From 006b1d0a579e36448983b0a4d624805d7230ef4e Mon Sep 17 00:00:00 2001
From: Lucas Smith <me@lucasjamessmith.me>
Date: Fri, 20 Feb 2026 11:36:20 +1100
Subject: [PATCH] feat: per-recipient envelope expiration (#2519)

---
 .../calm-violet-tide-envelope-expiration.md   | 519 ++++++++++++++++++
 .../embed/authoring/configure-fields-view.tsx |   4 +-
 .../embed/embed-recipient-expired.tsx         |  46 ++
 .../forms/document-preferences-form.tsx       |  38 ++
 .../document-page-view-recipients.tsx         |  54 +-
 .../envelope-editor-settings-dialog.tsx       |  42 +-
 .../o.$orgUrl.settings.document.tsx           |   2 +
 .../t.$teamUrl+/settings.document.tsx         |   2 +
 .../_recipient+/sign.$token+/_index.tsx       |  24 +-
 .../_recipient+/sign.$token+/expired.tsx      | 114 ++++
 apps/remix/app/routes/embed+/_v0+/_layout.tsx |   5 +
 .../app/routes/embed+/_v0+/sign.$token.tsx    |  25 +-
 apps/remix/server/router.ts                   |   5 +
 package-lock.json                             |  13 +
 package.json                                  |   1 +
 packages/api/v1/schema.ts                     |   7 +-
 .../e2e/api/v2/envelopes-api.spec.ts          |   3 +
 .../envelope-expiration-send.spec.ts          | 291 ++++++++++
 .../envelope-expiration-settings.spec.ts      | 150 +++++
 .../envelope-expiration-signing.spec.ts       | 131 +++++
 .../organisation-team-preferences.spec.ts     |   9 +-
 .../template-recipient-expired.tsx            |  54 ++
 .../email/templates/recipient-expired.tsx     |  68 +++
 packages/lib/constants/envelope-expiration.ts |  66 +++
 packages/lib/errors/app-error.ts              |   2 +
 packages/lib/jobs/client.ts                   |   6 +
 packages/lib/jobs/client/_internal/job.ts     |   5 +
 packages/lib/jobs/client/base.ts              |  10 +
 packages/lib/jobs/client/client.ts            |  11 +
 packages/lib/jobs/client/inngest.ts           |   9 +-
 packages/lib/jobs/client/local.ts             | 153 +++++-
 ...d-owner-recipient-expired-email.handler.ts | 117 ++++
 .../send-owner-recipient-expired-email.ts     |  32 ++
 .../expire-recipients-sweep.handler.ts        |  53 ++
 .../internal/expire-recipients-sweep.ts       |  30 +
 .../process-recipient-expired.handler.ts      |  95 ++++
 .../internal/process-recipient-expired.ts     |  31 ++
 .../document/complete-document-with-token.ts  |   3 +
 .../document/reject-document-with-token.ts    |  11 +-
 .../server-only/document/resend-document.ts   |  23 +-
 .../lib/server-only/document/send-document.ts |  23 +
 ...et-envelope-for-direct-template-signing.ts |   1 +
 .../get-envelope-for-recipient-signing.ts     |  10 +-
 .../field/remove-signed-field-with-token.ts   |   3 +
 .../field/sign-field-with-token.ts            |   3 +
 .../template/create-document-from-template.ts |   4 +
 .../webhooks/trigger/generate-sample-data.ts  |  97 +++-
 .../webhooks/zapier/list-documents.ts         |   4 +-
 packages/lib/types/document-audit-logs.ts     |  14 +
 packages/lib/types/document-email.ts          |   9 +
 packages/lib/types/document-meta.ts           |   2 +
 packages/lib/types/document.ts                |   1 +
 packages/lib/types/envelope.ts                |   1 +
 packages/lib/types/recipient.ts               |  12 +-
 packages/lib/types/webhook-payload.ts         |   6 +-
 packages/lib/utils/document-audit-logs.ts     |   8 +
 packages/lib/utils/document.ts                |   4 +
 packages/lib/utils/organisations.ts           |   4 +
 packages/lib/utils/recipients.ts              |  21 +
 packages/lib/utils/teams.ts                   |   3 +
 .../migration.sql                             |  18 +
 packages/prisma/schema.prisma                 |  52 +-
 .../envelope-router/use-envelope.types.ts     |   2 +
 .../update-organisation-settings.ts           |   3 +
 .../update-organisation-settings.types.ts     |   2 +
 .../team-router/update-team-settings.ts       |   3 +
 .../team-router/update-team-settings.types.ts |   2 +
 .../trpc/server/template-router/schema.ts     |   2 +
 .../document/document-email-checkboxes.tsx    |  67 ++-
 .../document/expiration-period-picker.tsx     | 153 ++++++
 70 files changed, 2705 insertions(+), 93 deletions(-)
 create mode 100644 .agents/plans/calm-violet-tide-envelope-expiration.md
 create mode 100644 apps/remix/app/components/embed/embed-recipient-expired.tsx
 create mode 100644 apps/remix/app/routes/_recipient+/sign.$token+/expired.tsx
 create mode 100644 packages/app-tests/e2e/envelopes/envelope-expiration-send.spec.ts
 create mode 100644 packages/app-tests/e2e/envelopes/envelope-expiration-settings.spec.ts
 create mode 100644 packages/app-tests/e2e/envelopes/envelope-expiration-signing.spec.ts
 create mode 100644 packages/email/template-components/template-recipient-expired.tsx
 create mode 100644 packages/email/templates/recipient-expired.tsx
 create mode 100644 packages/lib/constants/envelope-expiration.ts
 create mode 100644 packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.handler.ts
 create mode 100644 packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.ts
 create mode 100644 packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts
 create mode 100644 packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts
 create mode 100644 packages/lib/jobs/definitions/internal/process-recipient-expired.handler.ts
 create mode 100644 packages/lib/jobs/definitions/internal/process-recipient-expired.ts
 create mode 100644 packages/prisma/migrations/20260219091107_add_recipient_expirations/migration.sql
 create mode 100644 packages/ui/components/document/expiration-period-picker.tsx

diff --git a/.agents/plans/calm-violet-tide-envelope-expiration.md b/.agents/plans/calm-violet-tide-envelope-expiration.md
new file mode 100644
index 000000000..b2e8506ec
--- /dev/null
+++ b/.agents/plans/calm-violet-tide-envelope-expiration.md
@@ -0,0 +1,519 @@
+---
+date: 2026-02-10
+title: Envelope Expiration
+---
+
+## Summary
+
+Envelopes (documents sent for signing) should automatically expire after a configurable period, preventing recipients from completing stale documents. Expiration is tracked **per-recipient** — when a recipient's signing window lapses, the document owner is notified and can resend (extending the deadline) or cancel. The document itself stays PENDING so other recipients can continue signing.
+
+**Settings cascade**: Organisation → Team → Document (each level can override the prior).
+**Default**: 1 month from when the envelope is sent (transitions to PENDING).
+
+---
+
+## 1. Database Schema Changes
+
+### 1.1 Expiration period data shape
+
+Store expiration as a structured JSON object rather than an enum or raw milliseconds. This avoids the enum treadmill (adding `FOUR_MONTHS` later requires a migration) while keeping values validated and meaningful.
+
+**Zod schema** (defined in `packages/lib/constants/envelope-expiration.ts`):
+
+```typescript
+export const ZEnvelopeExpirationPeriod = z.union([
+  z.object({ unit: z.enum(['day', 'week', 'month', 'year']), amount: z.number().int().min(1) }),
+  z.object({ disabled: z.literal(true) }),
+]);
+
+export type TEnvelopeExpirationPeriod = z.infer<typeof ZEnvelopeExpirationPeriod>;
+```
+
+Semantics:
+
+- `null` on `DocumentMeta` / `TeamGlobalSettings` = inherit from parent
+- `{ disabled: true }` = explicitly never expires
+- `{ unit: 'month', amount: 1 }` = expires in 1 month
+
+No Prisma enum is needed — the period is stored as `Json?` on the relevant models (see sections 1.3 and 1.4).
+
+### 1.2 Add expiration fields to `Recipient`
+
+```prisma
+model Recipient {
+  // ... existing fields
+  expiresAt              DateTime?
+  expirationNotifiedAt   DateTime?   // null = not yet notified; set when owner notification sent
+
+  @@index([expiresAt])
+}
+```
+
+`expiresAt` is a computed timestamp set when the envelope transitions to PENDING (at send time). It is calculated from the effective expiration period. Storing the concrete timestamp rather than a relative duration means:
+
+- Sweep queries are simple (`WHERE expiresAt <= NOW() AND expirationNotifiedAt IS NULL`)
+- No need to re-resolve the settings cascade at query time
+- The sender can see the exact deadline in the UI
+- The index on `expiresAt` ensures the expiration sweep query is efficient
+
+`expirationNotifiedAt` tracks whether the owner has already been notified about this recipient's expiration, making the notification job idempotent.
+
+### 1.3 Add expiration period to settings models
+
+**OrganisationGlobalSettings** (JSON, application-level default):
+
+```prisma
+model OrganisationGlobalSettings {
+  // ... existing fields
+  envelopeExpirationPeriod Json?
+}
+```
+
+Prisma `@default` doesn't work for `Json` columns, so the application-level default (`{ unit: 'month', amount: 1 }`) is applied in `extractDerivedTeamSettings` / `extractDerivedDocumentMeta` when the value is null. The migration should backfill existing rows with `{ "unit": "month", "amount": 1 }`.
+
+**TeamGlobalSettings** (nullable, null = inherit from org):
+
+```prisma
+model TeamGlobalSettings {
+  // ... existing fields
+  envelopeExpirationPeriod Json?
+}
+```
+
+### 1.4 Add expiration period to DocumentMeta
+
+This allows per-document override during the document editing flow:
+
+```prisma
+model DocumentMeta {
+  // ... existing fields
+  envelopeExpirationPeriod Json?
+}
+```
+
+When null on DocumentMeta, the resolved team/org setting is used at send time. Validated at write time using `ZEnvelopeExpirationPeriod.nullable()`.
+
+**Important**: `envelopeExpirationPeriod` on `DocumentMeta` is a user-facing preference that may be set during the draft editing flow. It does NOT determine the final expiration — that is resolved at send time (see section 2.3). The value stored here is just the user's selection in the document editor.
+
+---
+
+## 2. Expiration Period Resolution
+
+### 2.1 Duration mapping
+
+Add to `packages/lib/constants/envelope-expiration.ts` alongside the Zod schema:
+
+```typescript
+import { Duration } from 'luxon';
+
+const UNIT_TO_LUXON_KEY: Record<TEnvelopeExpirationPeriod['unit'], string> = {
+  day: 'days',
+  week: 'weeks',
+  month: 'months',
+  year: 'years',
+};
+
+export const DEFAULT_ENVELOPE_EXPIRATION_PERIOD: TEnvelopeExpirationPeriod = {
+  unit: 'month',
+  amount: 1,
+};
+
+export const getEnvelopeExpirationDuration = (period: TEnvelopeExpirationPeriod): Duration => {
+  return Duration.fromObject({ [UNIT_TO_LUXON_KEY[period.unit]]: period.amount });
+};
+```
+
+### 2.2 Settings cascade integration
+
+`extractDerivedTeamSettings()` in `packages/lib/utils/teams.ts` needs **no code changes** — it iterates `Object.keys(derivedSettings)` and overrides with non-null team values at runtime. The new `envelopeExpirationPeriod` field on both `OrganisationGlobalSettings` and `TeamGlobalSettings` will be automatically picked up.
+
+Update `extractDerivedDocumentMeta()` in `packages/lib/utils/document.ts` to include the new field:
+
+```typescript
+envelopeExpirationPeriod: meta.envelopeExpirationPeriod ?? settings.envelopeExpirationPeriod,
+```
+
+### 2.3 Compute `expiresAt` at send time
+
+The expiration period is **locked at send time** — when the envelope transitions to PENDING. The concrete `expiresAt` timestamp is computed for each recipient when the document is actually sent.
+
+In `packages/lib/server-only/document/send-document.ts`:
+
+```typescript
+// Resolve effective period: document meta -> team/org settings -> default
+const rawPeriod =
+  envelope.documentMeta?.envelopeExpirationPeriod ?? settings.envelopeExpirationPeriod;
+
+const expiresAt = resolveExpiresAt(rawPeriod);
+
+// Inside the $transaction, for each recipient:
+await tx.recipient.updateMany({
+  where: { envelopeId: envelope.id },
+  data: { expiresAt },
+});
+```
+
+### 2.4 Compute `expiresAt` in the direct template flow
+
+`create-document-from-direct-template.ts` creates envelopes directly as PENDING and then calls `sendDocument` afterward. Since `sendDocument` handles setting `expiresAt` on recipients, the direct template flow doesn't need to set it directly — `sendDocument` handles it.
+
+---
+
+## 3. Cron Job Infrastructure (New)
+
+The current job system is purely event-triggered. Inngest natively supports cron-triggered functions, but the local provider (used in dev and by self-hosters who don't want a third-party dependency) has no scheduling capability. This section adds cron support to the local provider to maintain feature parity.
+
+### 3.1 Extend `JobDefinition` with cron support
+
+Add an optional `cron` field to the trigger type in `packages/lib/jobs/client/_internal/job.ts`:
+
+```typescript
+export type JobDefinition<Name extends string = string, Schema = any> = {
+  id: string;
+  name: string;
+  version: string;
+  enabled?: boolean;
+  optimizeParallelism?: boolean;
+  trigger: {
+    name: Name;
+    schema?: z.ZodType<Schema>;
+    /** Cron expression (e.g. "* * * * *"). When set, the job runs on a schedule. */
+    cron?: string;
+  };
+  handler: (options: { payload: Schema; io: JobRunIO }) => Promise<Json | void>;
+};
+```
+
+### 3.2 Inngest provider: wire up native cron
+
+In `packages/lib/jobs/client/inngest.ts`, when defining a function, check for `cron`:
+
+```typescript
+defineJob(job) {
+  if (job.trigger.cron) {
+    this._functions.push(
+      this._client.createFunction(
+        { id: job.id, name: job.name },
+        { cron: job.trigger.cron },
+        async ({ step, logger }) => {
+          const io = convertInngestIoToJobRunIo(step, logger, this);
+          await job.handler({ payload: {} as any, io });
+        },
+      ),
+    );
+  } else {
+    // Existing event-triggered logic (unchanged)
+  }
+}
+```
+
+### 3.3 Local provider: poller + deterministic `BackgroundJob` IDs
+
+Use the existing `BackgroundJob` table for multi-instance dedupe instead of advisory locks. This approach keeps implementation Prisma-only (no raw SQL), works for single-instance and multi-instance deployments, and preserves existing retry/visibility behavior.
+
+**On `defineJob()`**: If the job has a `cron` field, register an in-process scheduler entry and start a lightweight poller (every 30s with jitter).
+
+**Each poll tick**:
+
+1. Evaluate whether the cron schedule has one or more due run slots since the last tick (use a real cron parser, e.g. `cron-parser`)
+2. For each due slot, build a deterministic run ID from job ID + scheduled slot time
+3. Create a `BackgroundJob` row with that deterministic ID using Prisma
+4. If insert succeeds → enqueue via the existing local job pipeline
+5. If insert fails with Prisma `P2002` (unique violation) → another node already enqueued that run, skip
+
+### 3.4 Summary of changes to the job system
+
+| File                                        | Change                                                           |
+| ------------------------------------------- | ---------------------------------------------------------------- |
+| `packages/lib/jobs/client/_internal/job.ts` | Add optional `cron` field to `trigger` type                      |
+| `packages/lib/jobs/client/local.ts`         | Add cron poller + deterministic `BackgroundJob.id` dedupe        |
+| `packages/lib/jobs/client/inngest.ts`       | Wire up `{ cron: ... }` in `createFunction` for cron jobs        |
+| `packages/lib/jobs/client/_internal/*`      | Add cron helper utilities (`getDueCronSlots`, run ID generation) |
+
+---
+
+## 4. Expiration Processing
+
+### 4.1 Two-job architecture
+
+Expiration uses two jobs: a **sweep dispatcher** that runs on a cron schedule and finds expired recipients, and an **individual notification job** that handles the audit log, owner notification email, and webhook for a single recipient. This separation means:
+
+- The sweep is lightweight and fast (just a query + N job triggers)
+- Each recipient's expiration notification is independently retryable
+- The individual jobs are idempotent — they check `expirationNotifiedAt IS NULL` before processing
+
+### 4.2 Sweep job: `EXPIRE_RECIPIENTS_SWEEP_JOB`
+
+A cron-triggered job that runs every minute to find and dispatch notifications for expired recipients.
+
+**Definition:** `packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts`
+
+**Handler:** `packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts`
+
+```typescript
+const expiredRecipients = await prisma.recipient.findMany({
+  where: {
+    expiresAt: { lte: new Date() },
+    expirationNotifiedAt: null,
+    signingStatus: { notIn: [SigningStatus.SIGNED, SigningStatus.REJECTED] },
+    envelope: { status: DocumentStatus.PENDING },
+  },
+  select: { id: true },
+  take: 100,
+});
+
+for (const recipient of expiredRecipients) {
+  await jobs.triggerJob({
+    name: 'internal.notify-recipient-expired',
+    payload: { recipientId: recipient.id },
+  });
+}
+```
+
+### 4.3 Individual notification job: `NOTIFY_RECIPIENT_EXPIRED_JOB`
+
+An event-triggered job that handles a single recipient's expiration.
+
+**Definition:** `packages/lib/jobs/definitions/internal/notify-recipient-expired.ts`
+
+**Handler:** `packages/lib/jobs/definitions/internal/notify-recipient-expired.handler.ts`
+
+The handler:
+
+1. Fetches the recipient (with guard: `expirationNotifiedAt IS NULL` + not signed/rejected)
+2. Sets `recipient.expirationNotifiedAt = now()` (idempotency)
+3. Creates audit log entry with `DOCUMENT_RECIPIENT_EXPIRED` type
+4. Sends email notification to the **document owner** (inline — no separate email job)
+5. The document stays PENDING — the owner decides whether to resend or cancel
+
+### 4.4 Register in job client
+
+Add `EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION` and `NOTIFY_RECIPIENT_EXPIRED_JOB_DEFINITION` to the job registry in `packages/lib/jobs/client.ts`.
+
+### 4.5 Email template: Recipient Expired
+
+Target the **document owner**:
+
+- Subject: `Signing window expired for "{recipientName}" on "{documentTitle}"`
+- Body: "The signing window for {recipientName} ({recipientEmail}) on document {title} has expired. You can resend the document to extend their deadline or cancel the document."
+- Include a "View Document" link to the document page in the app
+
+Template files:
+
+- `packages/email/templates/recipient-expired.tsx` — wrapper
+- `packages/email/template-components/template-recipient-expired.tsx` — body
+
+### 4.6 Recipient signing guard
+
+In the signing flow, check `recipient.expiresAt` before allowing any signing action. Note that the document stays PENDING even after recipient expiration, so the existing `status !== PENDING` guard does not block expired recipients — an explicit expiration check is required:
+
+```typescript
+if (recipient.expiresAt && recipient.expiresAt <= new Date()) {
+  throw new AppError(AppErrorCode.RECIPIENT_EXPIRED, {
+    message: 'Recipient signing window has expired',
+  });
+}
+```
+
+**Files to update:**
+
+- `packages/lib/server-only/document/complete-document-with-token.ts`
+- `packages/lib/server-only/field/sign-field-with-token.ts`
+- `packages/lib/server-only/field/remove-signed-field-with-token.ts`
+- `packages/lib/server-only/document/reject-document-with-token.ts`
+
+---
+
+## 5. UI Design
+
+### 5.1 Expiration Period Selector Component
+
+Use a number input + unit selector combo. This gives organisations full flexibility to configure any duration without needing schema changes for new options.
+
+**Layout**: A horizontal group with:
+
+- A number `<Input>` (min 1, integer)
+- A `<Select>` for the unit (`day`, `week`, `month`, `year`)
+- A "Never expires" toggle/checkbox that disables the duration inputs and sets the value to `{ disabled: true }`
+
+At the team level, include an "Inherit from organisation" option that clears the value to `null`.
+
+**Validation**: Use `ZEnvelopeExpirationPeriod` for form validation.
+
+### 5.2 Organisation Settings → Document Preferences
+
+Add a "Default Envelope Expiration" field to the `DocumentPreferencesForm` component. At the org level, there is no "Inherit" option — it must have a concrete value (default: `{ unit: 'month', amount: 1 }`).
+
+### 5.3 Team Settings → Document Preferences
+
+Same field as org, but with the additional "Inherit from organisation" option (stored as `null`).
+
+### 5.4 Document Editor → Settings Step
+
+Add the expiration selector to `packages/ui/primitives/document-flow/add-settings.tsx` inside the "Advanced Options" accordion.
+
+Label: **"Expiration"**
+Description: _"How long recipients have to complete this document after it is sent."_
+
+### 5.5 Recipient Signing Page — Expired State
+
+When a recipient visits a signing link for an expired recipient:
+
+- Redirect to `/sign/{token}/expired`
+- Show a clear, non-alarming message: "Your signing window has expired. Please contact the sender for a new invitation."
+- Do not show the signing form or fields
+- The `isExpired` flag in `get-envelope-for-recipient-signing.ts` is derived from `recipient.expiresAt`
+
+### 5.6 Embed Signing — Expired State
+
+Embed signing routes handle recipient expiration by throwing `embed-recipient-expired`:
+
+- `apps/remix/app/routes/embed+/_v0+/sign.$token.tsx` — both V1 and V2 loaders check expiration
+- The embed error boundary renders an `EmbedRecipientExpired` component
+- Direct templates (`direct.$token.tsx`) create fresh recipients so `isExpired` is always `false`
+
+---
+
+## 6. API / TRPC Changes
+
+### 6.1 Update settings mutation schemas
+
+- `packages/trpc/server/organisation-router/update-organisation-settings.types.ts` — add `envelopeExpirationPeriod: ZEnvelopeExpirationPeriod` (non-nullable at org level)
+- `packages/trpc/server/team-router/update-team-settings.types.ts` — add `envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullable()` (null = inherit from org)
+
+### 6.2 Update document mutation schemas
+
+- `packages/lib/types/document-meta.ts` — add `envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullable()` to the meta schema
+- `packages/trpc/server/document-router/create-document.types.ts` — include in meta
+- `packages/trpc/server/document-router/update-document.types.ts` — include in meta
+- `packages/trpc/server/document-router/distribute-document.types.ts` — include in meta
+
+### 6.3 Expose `expiresAt` in recipient responses
+
+Ensure `expiresAt` and `expirationNotifiedAt` are returned when fetching recipients/documents so the UI can display expiration status.
+
+### 6.4 Webhook / API schema updates
+
+- Recipient schema includes `expiresAt` and `expirationNotifiedAt` fields (replacing the old `expired` field)
+- Update `packages/api/v1/schema.ts`, webhook payload types, zapier integration, and sample data generators
+
+---
+
+## 7. Edge Cases & Considerations
+
+### 7.1 Already-sent documents
+
+The migration should NOT retroactively expire existing recipients. `expiresAt` will be null for all existing recipients, meaning they never expire (backward-compatible).
+
+### 7.2 Re-sending / redistributing
+
+When `redistribute` is called on a PENDING document, `expiresAt` should be refreshed on all eligible recipients. Redistributing signals active intent, so the clock should restart.
+
+**Implementation**: `resendDocument` refreshes `recipient.expiresAt` for all recipients that haven't signed/rejected yet.
+
+### 7.3 Multi-recipient partial expiration
+
+If some recipients have signed and others expire, the document stays PENDING. This is the key advantage over document-level expiration — the owner can resend to extend the expired recipients' deadlines without affecting those who've already signed.
+
+### 7.4 Partial completion
+
+Partial signatures are preserved. The document is not sealed/completed until all required recipients have signed (or the owner cancels).
+
+### 7.5 Timezone handling
+
+`expiresAt` is stored as UTC. Display in the sender's configured timezone.
+
+### 7.6 Race condition: signing at expiration time
+
+The signing guard checks `recipient.expiresAt` in application code before the signing operation. The notification job's guard (`expirationNotifiedAt IS NULL` + `signingStatus NOT IN (SIGNED, REJECTED)`) prevents double-notifications. If a recipient signs just before expiration, the sweep's `signingStatus` filter skips them.
+
+### 7.7 Direct template flow
+
+`create-document-from-direct-template.ts` creates envelopes directly as PENDING then calls `sendDocument`. Since `sendDocument` sets `recipient.expiresAt`, no special handling is needed in the direct template flow.
+
+---
+
+## 8. Migration Plan
+
+1. Add Prisma schema changes (`expiresAt` + `expirationNotifiedAt` on Recipient, `Json?` fields on settings models, index)
+2. Generate and run migration
+3. Backfill: set `envelopeExpirationPeriod` to `{ "unit": "month", "amount": 1 }` on all existing `OrganisationGlobalSettings` rows
+4. No backfill on `Recipient.expiresAt` — existing recipients keep null (never expire)
+5. Deploy backend changes (jobs, guards, email template)
+6. Deploy frontend changes (settings UI, document editor, signing page, embeds)
+
+---
+
+## 9. Files to Create or Modify
+
+### New Files
+
+- `packages/lib/constants/envelope-expiration.ts` — `ZEnvelopeExpirationPeriod` schema, types, `DEFAULT_ENVELOPE_EXPIRATION_PERIOD`, `getEnvelopeExpirationDuration()`, `resolveExpiresAt()` helper
+- `packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts` — cron sweep job definition
+- `packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts` — cron sweep handler
+- `packages/lib/jobs/definitions/internal/notify-recipient-expired.ts` — individual notification job definition
+- `packages/lib/jobs/definitions/internal/notify-recipient-expired.handler.ts` — notification handler (includes inline email sending)
+- `packages/email/templates/recipient-expired.tsx` — email template wrapper
+- `packages/email/template-components/template-recipient-expired.tsx` — email template body
+- `apps/remix/app/components/embed/embed-recipient-expired.tsx` — embed expired component
+
+### Modified Files
+
+**Job system (cron infrastructure):**
+
+- `packages/lib/jobs/client/_internal/job.ts` — add optional `cron` field to `trigger` type
+- `packages/lib/jobs/client/local.ts` — add cron poller + deterministic `BackgroundJob.id` dedupe
+- `packages/lib/jobs/client/inngest.ts` — wire up `{ cron: ... }` in `createFunction`
+- `packages/lib/jobs/client/_internal/*` — add cron helper utilities (slot calc + run ID)
+- `packages/lib/jobs/client.ts` — register new jobs
+
+**Schema & data layer:**
+
+- `packages/prisma/schema.prisma` — model changes + index
+- `packages/lib/utils/document.ts` — `extractDerivedDocumentMeta` (add `envelopeExpirationPeriod`)
+- `packages/lib/server-only/document/send-document.ts` — resolve settings + compute and set `recipient.expiresAt`
+- `packages/lib/server-only/template/create-document-from-direct-template.ts` — no changes (sendDocument handles it)
+- `packages/lib/server-only/document/resend-document.ts` — refresh `recipient.expiresAt` on redistribute
+- `packages/lib/server-only/document/complete-document-with-token.ts` — recipient expiration guard
+- `packages/lib/server-only/field/sign-field-with-token.ts` — recipient expiration guard
+- `packages/lib/server-only/field/remove-signed-field-with-token.ts` — recipient expiration guard
+- `packages/lib/server-only/document/reject-document-with-token.ts` — recipient expiration guard
+
+**Error handling:**
+
+- `packages/lib/errors/app-error.ts` — add `RECIPIENT_EXPIRED` error code
+
+**Audit logs:**
+
+- `packages/lib/types/document-audit-logs.ts` — add `DOCUMENT_RECIPIENT_EXPIRED` type with `recipientEmail`/`recipientName` data fields
+- `packages/lib/utils/document-audit-logs.ts` — add human-readable rendering for `DOCUMENT_RECIPIENT_EXPIRED`
+
+**Signing page:**
+
+- `packages/lib/server-only/envelope/get-envelope-for-recipient-signing.ts` — derive `isExpired` from `recipient.expiresAt`
+- `apps/remix/app/routes/_recipient+/sign.$token+/_index.tsx` — keep redirect to expired page using `isExpired`
+
+**Embeds:**
+
+- `apps/remix/app/routes/embed+/_v0+/sign.$token.tsx` — check recipient expiration in V1/V2 loaders
+- `apps/remix/app/routes/embed+/_v0+/_layout.tsx` — handle `embed-recipient-expired` in error boundary
+
+**Webhook / API:**
+
+- `packages/lib/types/recipient.ts` — add `expiresAt`/`expirationNotifiedAt` to recipient type
+- `packages/lib/types/webhook-payload.ts` — add `expiresAt`/`expirationNotifiedAt` to webhook recipient
+- `packages/lib/server-only/webhooks/trigger/generate-sample-data.ts` — update sample data
+- `packages/lib/server-only/webhooks/zapier/list-documents.ts` — update zapier recipient shape
+- `packages/api/v1/schema.ts` — add `expiresAt` to API recipient schema
+
+**TRPC / settings:**
+
+- `packages/trpc/server/organisation-router/update-organisation-settings.types.ts`
+- `packages/trpc/server/team-router/update-team-settings.types.ts`
+- `packages/lib/types/document-meta.ts`
+
+**UI:**
+
+- `apps/remix/app/components/forms/document-preferences-form.tsx` — add expiration period picker
+- `packages/ui/primitives/document-flow/add-settings.tsx` — add expiration field
+- `packages/ui/primitives/document-flow/add-settings.types.ts` — add to schema
diff --git a/apps/remix/app/components/embed/authoring/configure-fields-view.tsx b/apps/remix/app/components/embed/authoring/configure-fields-view.tsx
index 915c40b8b..0a8b43e58 100644
--- a/apps/remix/app/components/embed/authoring/configure-fields-view.tsx
+++ b/apps/remix/app/components/embed/authoring/configure-fields-view.tsx
@@ -115,7 +115,9 @@ export const ConfigureFieldsView = ({
       templateId: null,
       token: '',
       documentDeletedAt: null,
-      expired: null,
+      expired: null, // !: deprecated Not in use. To be removed in a future migration.
+      expiresAt: null,
+      expirationNotifiedAt: null,
       signedAt: null,
       authOptions: null,
       rejectionReason: null,
diff --git a/apps/remix/app/components/embed/embed-recipient-expired.tsx b/apps/remix/app/components/embed/embed-recipient-expired.tsx
new file mode 100644
index 000000000..821ac0044
--- /dev/null
+++ b/apps/remix/app/components/embed/embed-recipient-expired.tsx
@@ -0,0 +1,46 @@
+import { useEffect, useState } from 'react';
+
+import { Trans } from '@lingui/react/macro';
+
+export const EmbedRecipientExpired = () => {
+  const [hasPostedMessage, setHasPostedMessage] = useState(false);
+
+  useEffect(() => {
+    if (window.parent && !hasPostedMessage) {
+      window.parent.postMessage(
+        {
+          action: 'recipient-expired',
+          data: null,
+        },
+        '*',
+      );
+    }
+
+    setHasPostedMessage(true);
+  }, [hasPostedMessage]);
+
+  if (!hasPostedMessage) {
+    return null;
+  }
+
+  return (
+    <div className="embed--RecipientExpired relative mx-auto flex min-h-[100dvh] max-w-screen-lg flex-col items-center justify-center p-6">
+      <h3 className="text-center text-2xl font-bold text-foreground">
+        <Trans>Signing Window Expired</Trans>
+      </h3>
+
+      <div className="mt-8 max-w-[50ch] text-center">
+        <p className="text-sm text-muted-foreground">
+          <Trans>
+            Your signing window for this document has expired. Please contact the sender for a new
+            invitation.
+          </Trans>
+        </p>
+
+        <p className="mt-4 text-sm text-muted-foreground">
+          <Trans>Please check with the parent application for more information.</Trans>
+        </p>
+      </div>
+    </div>
+  );
+};
diff --git a/apps/remix/app/components/forms/document-preferences-form.tsx b/apps/remix/app/components/forms/document-preferences-form.tsx
index f8f70fa52..c3d425abb 100644
--- a/apps/remix/app/components/forms/document-preferences-form.tsx
+++ b/apps/remix/app/components/forms/document-preferences-form.tsx
@@ -11,6 +11,10 @@ import { useCurrentOrganisation } from '@documenso/lib/client-only/providers/org
 import { useSession } from '@documenso/lib/client-only/providers/session';
 import { DATE_FORMATS } from '@documenso/lib/constants/date-formats';
 import { DOCUMENT_SIGNATURE_TYPES, DocumentSignatureType } from '@documenso/lib/constants/document';
+import {
+  type TEnvelopeExpirationPeriod,
+  ZEnvelopeExpirationPeriod,
+} from '@documenso/lib/constants/envelope-expiration';
 import {
   SUPPORTED_LANGUAGES,
   SUPPORTED_LANGUAGE_CODES,
@@ -27,6 +31,7 @@ import { isPersonalLayout } from '@documenso/lib/utils/organisations';
 import { recipientAbbreviation } from '@documenso/lib/utils/recipient-formatter';
 import { extractTeamSignatureSettings } from '@documenso/lib/utils/teams';
 import { DocumentSignatureSettingsTooltip } from '@documenso/ui/components/document/document-signature-settings-tooltip';
+import { ExpirationPeriodPicker } from '@documenso/ui/components/document/expiration-period-picker';
 import { RecipientRoleSelect } from '@documenso/ui/components/recipient/recipient-role-select';
 import { Alert } from '@documenso/ui/primitives/alert';
 import { AvatarWithText } from '@documenso/ui/primitives/avatar';
@@ -70,6 +75,7 @@ export type TDocumentPreferencesFormSchema = {
   defaultRecipients: TDefaultRecipients | null;
   delegateDocumentOwnership: boolean | null;
   aiFeaturesEnabled: boolean | null;
+  envelopeExpirationPeriod: TEnvelopeExpirationPeriod | null;
 };
 
 type SettingsSubset = Pick<
@@ -87,6 +93,7 @@ type SettingsSubset = Pick<
   | 'defaultRecipients'
   | 'delegateDocumentOwnership'
   | 'aiFeaturesEnabled'
+  | 'envelopeExpirationPeriod'
 >;
 
 export type DocumentPreferencesFormProps = {
@@ -126,6 +133,7 @@ export const DocumentPreferencesForm = ({
     defaultRecipients: ZDefaultRecipientsSchema.nullable(),
     delegateDocumentOwnership: z.boolean().nullable(),
     aiFeaturesEnabled: z.boolean().nullable(),
+    envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullable(),
   });
 
   const form = useForm<TDocumentPreferencesFormSchema>({
@@ -146,6 +154,7 @@ export const DocumentPreferencesForm = ({
         : null,
       delegateDocumentOwnership: settings.delegateDocumentOwnership,
       aiFeaturesEnabled: settings.aiFeaturesEnabled,
+      envelopeExpirationPeriod: settings.envelopeExpirationPeriod ?? null,
     },
     resolver: zodResolver(ZDocumentPreferencesFormSchema),
   });
@@ -669,6 +678,35 @@ export const DocumentPreferencesForm = ({
             )}
           />
 
+          <FormField
+            control={form.control}
+            name="envelopeExpirationPeriod"
+            render={({ field }) => (
+              <FormItem className="flex-1">
+                <FormLabel>
+                  <Trans>Default Envelope Expiration</Trans>
+                </FormLabel>
+
+                <FormControl>
+                  <ExpirationPeriodPicker
+                    value={field.value}
+                    onChange={field.onChange}
+                    inheritLabel={canInherit ? t`Inherit from organisation` : undefined}
+                  />
+                </FormControl>
+
+                <FormDescription>
+                  <Trans>
+                    Controls how long recipients have to complete signing before the document
+                    expires. After expiration, recipients can no longer sign the document.
+                  </Trans>
+                </FormDescription>
+
+                <FormMessage />
+              </FormItem>
+            )}
+          />
+
           {isAiFeaturesConfigured && (
             <FormField
               control={form.control}
diff --git a/apps/remix/app/components/general/document/document-page-view-recipients.tsx b/apps/remix/app/components/general/document/document-page-view-recipients.tsx
index a134d75f4..b3f367302 100644
--- a/apps/remix/app/components/general/document/document-page-view-recipients.tsx
+++ b/apps/remix/app/components/general/document/document-page-view-recipients.tsx
@@ -9,19 +9,21 @@ import {
   AlertTriangle,
   CheckIcon,
   Clock,
+  Clock8Icon,
   MailIcon,
   MailOpenIcon,
   PenIcon,
   PlusIcon,
   UserIcon,
 } from 'lucide-react';
+import { DateTime } from 'luxon';
 import { Link, useSearchParams } from 'react-router';
 import { match } from 'ts-pattern';
 
 import { RECIPIENT_ROLES_DESCRIPTION } from '@documenso/lib/constants/recipient-roles';
 import type { TEnvelope } from '@documenso/lib/types/envelope';
 import { isDocumentCompleted } from '@documenso/lib/utils/document';
-import { formatSigningLink } from '@documenso/lib/utils/recipients';
+import { formatSigningLink, isRecipientExpired } from '@documenso/lib/utils/recipients';
 import { CopyTextButton } from '@documenso/ui/components/common/copy-text-button';
 import { SignatureIcon } from '@documenso/ui/icons/signature';
 import { AvatarWithText } from '@documenso/ui/primitives/avatar';
@@ -44,7 +46,7 @@ export const DocumentPageViewRecipients = ({
   envelope,
   documentRootPath,
 }: DocumentPageViewRecipientsProps) => {
-  const { _ } = useLingui();
+  const { _, i18n } = useLingui();
   const { toast } = useToast();
   const [searchParams, setSearchParams] = useSearchParams();
 
@@ -66,9 +68,9 @@ export const DocumentPageViewRecipients = ({
   }, [searchParams, setSearchParams]);
 
   return (
-    <section className="dark:bg-background border-border bg-widget flex flex-col rounded-xl border">
+    <section className="flex flex-col rounded-xl border border-border bg-widget dark:bg-background">
       <div className="flex flex-row items-center justify-between px-4 py-3">
-        <h1 className="text-foreground font-medium">
+        <h1 className="font-medium text-foreground">
           <Trans>Recipients</Trans>
         </h1>
 
@@ -87,7 +89,7 @@ export const DocumentPageViewRecipients = ({
         )}
       </div>
 
-      <ul className="text-muted-foreground divide-y border-t">
+      <ul className="divide-y border-t text-muted-foreground">
         {recipients.length === 0 && (
           <li className="flex flex-col items-center justify-center py-6 text-sm">
             <Trans>No recipients</Trans>
@@ -98,9 +100,9 @@ export const DocumentPageViewRecipients = ({
           <li key={recipient.id} className="flex items-center justify-between px-4 py-2.5 text-sm">
             <AvatarWithText
               avatarFallback={recipient.email.slice(0, 1).toUpperCase()}
-              primaryText={<p className="text-muted-foreground text-sm">{recipient.email}</p>}
+              primaryText={<p className="text-sm text-muted-foreground">{recipient.email}</p>}
               secondaryText={
-                <p className="text-muted-foreground/70 text-xs">
+                <p className="text-xs text-muted-foreground/70">
                   {_(RECIPIENT_ROLES_DESCRIPTION[recipient.role].roleName)}
                 </p>
               }
@@ -154,12 +156,41 @@ export const DocumentPageViewRecipients = ({
                 )}
 
               {envelope.status !== DocumentStatus.DRAFT &&
-                recipient.signingStatus === SigningStatus.NOT_SIGNED && (
+                recipient.signingStatus === SigningStatus.NOT_SIGNED &&
+                isRecipientExpired(recipient) && (
+                  <Badge variant="destructive">
+                    <Clock8Icon className="mr-1 h-3 w-3" />
+                    <Trans>Expired</Trans>
+                  </Badge>
+                )}
+
+              {envelope.status !== DocumentStatus.DRAFT &&
+                recipient.signingStatus === SigningStatus.NOT_SIGNED &&
+                !isRecipientExpired(recipient) &&
+                (recipient.expiresAt ? (
+                  <PopoverHover
+                    trigger={
+                      <Badge variant="secondary">
+                        <Clock className="mr-1 h-3 w-3" />
+                        <Trans>Pending</Trans>
+                      </Badge>
+                    }
+                  >
+                    <p className="text-xs text-muted-foreground">
+                      <Trans>
+                        Expires{' '}
+                        {recipient.expiresAt
+                          ? i18n.date(recipient.expiresAt, DateTime.DATETIME_MED)
+                          : 'N/A'}
+                      </Trans>
+                    </p>
+                  </PopoverHover>
+                ) : (
                   <Badge variant="secondary">
                     <Clock className="mr-1 h-3 w-3" />
                     <Trans>Pending</Trans>
                   </Badge>
-                )}
+                ))}
 
               {envelope.status !== DocumentStatus.DRAFT &&
                 recipient.signingStatus === SigningStatus.REJECTED && (
@@ -175,7 +206,7 @@ export const DocumentPageViewRecipients = ({
                       <Trans>Reason for rejection: </Trans>
                     </p>
 
-                    <p className="text-muted-foreground mt-1 text-sm">
+                    <p className="mt-1 text-sm text-muted-foreground">
                       {recipient.rejectionReason}
                     </p>
                   </PopoverHover>
@@ -183,7 +214,8 @@ export const DocumentPageViewRecipients = ({
 
               {envelope.status === DocumentStatus.PENDING &&
                 recipient.signingStatus === SigningStatus.NOT_SIGNED &&
-                recipient.role !== RecipientRole.CC && (
+                recipient.role !== RecipientRole.CC &&
+                !isRecipientExpired(recipient) && (
                   <TooltipProvider>
                     <Tooltip open={shouldHighlightCopyButtons && i === 0}>
                       <TooltipTrigger asChild>
diff --git a/apps/remix/app/components/general/envelope-editor/envelope-editor-settings-dialog.tsx b/apps/remix/app/components/general/envelope-editor/envelope-editor-settings-dialog.tsx
index 5c946f22c..4e6373825 100644
--- a/apps/remix/app/components/general/envelope-editor/envelope-editor-settings-dialog.tsx
+++ b/apps/remix/app/components/general/envelope-editor/envelope-editor-settings-dialog.tsx
@@ -22,6 +22,7 @@ import {
   DOCUMENT_DISTRIBUTION_METHODS,
   DOCUMENT_SIGNATURE_TYPES,
 } from '@documenso/lib/constants/document';
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import {
   SUPPORTED_LANGUAGES,
   SUPPORTED_LANGUAGE_CODES,
@@ -62,6 +63,7 @@ import {
   DocumentVisibilitySelect,
   DocumentVisibilityTooltip,
 } from '@documenso/ui/components/document/document-visibility-select';
+import { ExpirationPeriodPicker } from '@documenso/ui/components/document/expiration-period-picker';
 import { cn } from '@documenso/ui/lib/utils';
 import { Button } from '@documenso/ui/primitives/button';
 import { CardDescription, CardHeader, CardTitle } from '@documenso/ui/primitives/card';
@@ -135,6 +137,7 @@ export const ZAddSettingsFormSchema = z.object({
     signatureTypes: z.array(z.nativeEnum(DocumentSignatureType)).min(1, {
       message: msg`At least one signature type must be enabled`.id,
     }),
+    envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
   }),
 });
 
@@ -207,6 +210,7 @@ export const EnvelopeEditorSettingsDialog = ({
         emailReplyTo: envelope.documentMeta.emailReplyTo ?? undefined,
         emailSettings: ZDocumentEmailSettingsSchema.parse(envelope.documentMeta.emailSettings),
         signatureTypes: extractTeamSignatureSettings(envelope.documentMeta),
+        envelopeExpirationPeriod: envelope.documentMeta?.envelopeExpirationPeriod ?? null,
       },
     };
   };
@@ -245,6 +249,7 @@ export const EnvelopeEditorSettingsDialog = ({
       message,
       subject,
       emailReplyTo,
+      envelopeExpirationPeriod,
     } = data.meta;
 
     const parsedGlobalAccessAuth = z
@@ -273,6 +278,7 @@ export const EnvelopeEditorSettingsDialog = ({
           drawSignatureEnabled: signatureTypes.includes(DocumentSignatureType.DRAW),
           typedSignatureEnabled: signatureTypes.includes(DocumentSignatureType.TYPE),
           uploadSignatureEnabled: signatureTypes.includes(DocumentSignatureType.UPLOAD),
+          envelopeExpirationPeriod,
         },
       });
 
@@ -373,7 +379,7 @@ export const EnvelopeEditorSettingsDialog = ({
           <Form {...form}>
             <form onSubmit={form.handleSubmit(onFormSubmit)}>
               <fieldset
-                className="flex h-[45rem] max-h-[calc(100vh-14rem)] w-full flex-col space-y-6 overflow-y-auto px-6 pt-6"
+                className="flex h-[45rem] max-h-[calc(100vh-14rem)] w-full flex-col space-y-6 overflow-y-auto px-6 py-6"
                 disabled={form.formState.isSubmitting}
                 key={activeTab}
               >
@@ -636,6 +642,40 @@ export const EnvelopeEditorSettingsDialog = ({
                           </FormItem>
                         )}
                       />
+
+                      <FormField
+                        control={form.control}
+                        name="meta.envelopeExpirationPeriod"
+                        render={({ field }) => (
+                          <FormItem>
+                            <FormLabel className="flex flex-row items-center">
+                              <Trans>Expiration</Trans>
+                              <Tooltip>
+                                <TooltipTrigger>
+                                  <InfoIcon className="mx-2 h-4 w-4" />
+                                </TooltipTrigger>
+
+                                <TooltipContent className="max-w-xs text-muted-foreground">
+                                  <Trans>
+                                    How long recipients have to complete this document after it is
+                                    sent. Uses the team default when set to inherit.
+                                  </Trans>
+                                </TooltipContent>
+                              </Tooltip>
+                            </FormLabel>
+
+                            <FormControl>
+                              <ExpirationPeriodPicker
+                                value={field.value}
+                                onChange={field.onChange}
+                                disabled={envelopeHasBeenSent}
+                              />
+                            </FormControl>
+
+                            <FormMessage />
+                          </FormItem>
+                        )}
+                      />
                     </>
                   ))
                   .with('email', () => (
diff --git a/apps/remix/app/routes/_authenticated+/o.$orgUrl.settings.document.tsx b/apps/remix/app/routes/_authenticated+/o.$orgUrl.settings.document.tsx
index 3ad5f0785..fc6b0b644 100644
--- a/apps/remix/app/routes/_authenticated+/o.$orgUrl.settings.document.tsx
+++ b/apps/remix/app/routes/_authenticated+/o.$orgUrl.settings.document.tsx
@@ -60,6 +60,7 @@ export default function OrganisationSettingsDocumentPage() {
         defaultRecipients,
         delegateDocumentOwnership,
         aiFeaturesEnabled,
+        envelopeExpirationPeriod,
       } = data;
 
       if (
@@ -90,6 +91,7 @@ export default function OrganisationSettingsDocumentPage() {
           drawSignatureEnabled: signatureTypes.includes(DocumentSignatureType.DRAW),
           delegateDocumentOwnership: delegateDocumentOwnership,
           aiFeaturesEnabled,
+          envelopeExpirationPeriod: envelopeExpirationPeriod ?? undefined,
         },
       });
 
diff --git a/apps/remix/app/routes/_authenticated+/t.$teamUrl+/settings.document.tsx b/apps/remix/app/routes/_authenticated+/t.$teamUrl+/settings.document.tsx
index 7fc7a5aa8..a6089fddb 100644
--- a/apps/remix/app/routes/_authenticated+/t.$teamUrl+/settings.document.tsx
+++ b/apps/remix/app/routes/_authenticated+/t.$teamUrl+/settings.document.tsx
@@ -53,6 +53,7 @@ export default function TeamsSettingsPage() {
         defaultRecipients,
         delegateDocumentOwnership,
         aiFeaturesEnabled,
+        envelopeExpirationPeriod,
       } = data;
 
       await updateTeamSettings({
@@ -67,6 +68,7 @@ export default function TeamsSettingsPage() {
           includeAuditLog,
           defaultRecipients,
           aiFeaturesEnabled,
+          envelopeExpirationPeriod,
           ...(signatureTypes.length === 0
             ? {
                 typedSignatureEnabled: null,
diff --git a/apps/remix/app/routes/_recipient+/sign.$token+/_index.tsx b/apps/remix/app/routes/_recipient+/sign.$token+/_index.tsx
index ede85cafd..c7ba1eaaa 100644
--- a/apps/remix/app/routes/_recipient+/sign.$token+/_index.tsx
+++ b/apps/remix/app/routes/_recipient+/sign.$token+/_index.tsx
@@ -25,6 +25,7 @@ import { getTeamSettings } from '@documenso/lib/server-only/team/get-team-settin
 import { getUserByEmail } from '@documenso/lib/server-only/user/get-user-by-email';
 import { DocumentAccessAuth } from '@documenso/lib/types/document-auth';
 import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
+import { isRecipientExpired } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 import { SigningCard3D } from '@documenso/ui/components/signing-card';
 
@@ -140,6 +141,10 @@ const handleV1Loader = async ({ params, request }: Route.LoaderArgs) => {
     throw redirect(`/sign/${token}/rejected`);
   }
 
+  if (isRecipientExpired(recipient)) {
+    throw redirect(`/sign/${token}/expired`);
+  }
+
   if (
     document.status === DocumentStatus.COMPLETED ||
     recipient.signingStatus === SigningStatus.SIGNED
@@ -201,7 +206,8 @@ const handleV2Loader = async ({ params, request }: Route.LoaderArgs) => {
     return envelopeForSigning;
   }
 
-  const { envelope, recipient, isCompleted, isRejected, isRecipientsTurn } = envelopeForSigning;
+  const { envelope, recipient, isCompleted, isRejected, isExpired, isRecipientsTurn } =
+    envelopeForSigning;
 
   if (!isRecipientsTurn) {
     throw redirect(`/sign/${token}/waiting`);
@@ -233,12 +239,6 @@ const handleV2Loader = async ({ params, request }: Route.LoaderArgs) => {
     } as const;
   }
 
-  await viewedDocument({
-    token,
-    requestMetadata,
-    recipientAccessAuth: derivedRecipientAccessAuth,
-  }).catch(() => null);
-
   if (isRejected) {
     throw redirect(`/sign/${token}/rejected`);
   }
@@ -247,6 +247,16 @@ const handleV2Loader = async ({ params, request }: Route.LoaderArgs) => {
     throw redirect(envelope.documentMeta.redirectUrl || `/sign/${token}/complete`);
   }
 
+  if (isExpired) {
+    throw redirect(`/sign/${token}/expired`);
+  }
+
+  await viewedDocument({
+    token,
+    requestMetadata,
+    recipientAccessAuth: derivedRecipientAccessAuth,
+  }).catch(() => null);
+
   return {
     isDocumentAccessValid: true,
     envelopeForSigning,
diff --git a/apps/remix/app/routes/_recipient+/sign.$token+/expired.tsx b/apps/remix/app/routes/_recipient+/sign.$token+/expired.tsx
new file mode 100644
index 000000000..a5b3e3f7f
--- /dev/null
+++ b/apps/remix/app/routes/_recipient+/sign.$token+/expired.tsx
@@ -0,0 +1,114 @@
+import { Trans } from '@lingui/react/macro';
+import { TimerOffIcon } from 'lucide-react';
+import { Link } from 'react-router';
+
+import { getOptionalSession } from '@documenso/auth/server/lib/utils/get-session';
+import { useOptionalSession } from '@documenso/lib/client-only/providers/session';
+import { getDocumentAndSenderByToken } from '@documenso/lib/server-only/document/get-document-by-token';
+import { isRecipientAuthorized } from '@documenso/lib/server-only/document/is-recipient-authorized';
+import { getRecipientByToken } from '@documenso/lib/server-only/recipient/get-recipient-by-token';
+import { Badge } from '@documenso/ui/primitives/badge';
+import { Button } from '@documenso/ui/primitives/button';
+
+import { DocumentSigningAuthPageView } from '~/components/general/document-signing/document-signing-auth-page';
+import { truncateTitle } from '~/utils/truncate-title';
+
+import type { Route } from './+types/expired';
+
+export async function loader({ params, request }: Route.LoaderArgs) {
+  const { user } = await getOptionalSession(request);
+
+  const { token } = params;
+
+  if (!token) {
+    throw new Response('Not Found', { status: 404 });
+  }
+
+  const document = await getDocumentAndSenderByToken({
+    token,
+    requireAccessAuth: false,
+  }).catch(() => null);
+
+  if (!document) {
+    throw new Response('Not Found', { status: 404 });
+  }
+
+  const title = document.title;
+
+  const recipient = await getRecipientByToken({ token }).catch(() => null);
+
+  if (!recipient) {
+    throw new Response('Not Found', { status: 404 });
+  }
+
+  const isDocumentAccessValid = await isRecipientAuthorized({
+    type: 'ACCESS',
+    documentAuthOptions: document.authOptions,
+    recipient,
+    userId: user?.id,
+  });
+
+  const recipientEmail = recipient.email;
+
+  if (isDocumentAccessValid) {
+    return {
+      isDocumentAccessValid: true,
+      recipientEmail,
+      title,
+    };
+  }
+
+  return {
+    isDocumentAccessValid: false,
+    recipientEmail,
+  };
+}
+
+export default function ExpiredSigningPage({ loaderData }: Route.ComponentProps) {
+  const { sessionData } = useOptionalSession();
+  const user = sessionData?.user;
+
+  const { isDocumentAccessValid, recipientEmail, title } = loaderData;
+
+  if (!isDocumentAccessValid) {
+    return <DocumentSigningAuthPageView email={recipientEmail} />;
+  }
+
+  return (
+    <div className="flex flex-col items-center pt-24 lg:pt-36 xl:pt-44">
+      <Badge
+        variant="neutral"
+        size="default"
+        title={title}
+        className="mb-6 rounded-xl border bg-transparent"
+      >
+        {truncateTitle(title ?? '')}
+      </Badge>
+
+      <div className="flex flex-col items-center">
+        <div className="flex items-center gap-x-4">
+          <TimerOffIcon className="h-10 w-10 text-orange-500" />
+
+          <h2 className="max-w-[35ch] text-center text-2xl font-semibold leading-normal md:text-3xl lg:text-4xl">
+            <Trans>Signing Deadline Expired</Trans>
+          </h2>
+        </div>
+
+        <p className="mt-6 max-w-[60ch] text-center text-sm text-muted-foreground">
+          <Trans>
+            The signing deadline for this document has passed. Please contact the document owner if
+            you need a new copy to sign.
+          </Trans>
+        </p>
+
+        {user && (
+          <Button className="mt-6" asChild>
+            <Link to={`/`}>
+              <Trans>Return Home</Trans>
+            </Link>
+          </Button>
+        )}
+      </div>
+    </div>
+  );
+}
diff --git a/apps/remix/app/routes/embed+/_v0+/_layout.tsx b/apps/remix/app/routes/embed+/_v0+/_layout.tsx
index b1c535281..4d7d45eeb 100644
--- a/apps/remix/app/routes/embed+/_v0+/_layout.tsx
+++ b/apps/remix/app/routes/embed+/_v0+/_layout.tsx
@@ -13,6 +13,7 @@ import { EmbedDocumentCompleted } from '~/components/embed/embed-document-comple
 import { EmbedDocumentRejected } from '~/components/embed/embed-document-rejected';
 import { EmbedDocumentWaitingForTurn } from '~/components/embed/embed-document-waiting-for-turn';
 import { EmbedPaywall } from '~/components/embed/embed-paywall';
+import { EmbedRecipientExpired } from '~/components/embed/embed-recipient-expired';
 
 import type { Route } from './+types/_layout';
 
@@ -79,6 +80,10 @@ export function ErrorBoundary({ loaderData }: Route.ErrorBoundaryProps) {
       return <EmbedDocumentWaitingForTurn />;
     }
 
+    if (error.status === 403 && error.data.type === 'embed-recipient-expired') {
+      return <EmbedRecipientExpired />;
+    }
+
     // !: Not used at the moment, may be removed in the future.
     if (error.status === 403 && error.data.type === 'embed-document-rejected') {
       return <EmbedDocumentRejected />;
diff --git a/apps/remix/app/routes/embed+/_v0+/sign.$token.tsx b/apps/remix/app/routes/embed+/_v0+/sign.$token.tsx
index e3bf2b03b..157805d91 100644
--- a/apps/remix/app/routes/embed+/_v0+/sign.$token.tsx
+++ b/apps/remix/app/routes/embed+/_v0+/sign.$token.tsx
@@ -19,6 +19,7 @@ import { getRecipientsForAssistant } from '@documenso/lib/server-only/recipient/
 import { DocumentAccessAuth } from '@documenso/lib/types/document-auth';
 import { isDocumentCompleted } from '@documenso/lib/utils/document';
 import { extractDocumentAuthMethods } from '@documenso/lib/utils/document-auth';
+import { isRecipientExpired } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 
 import { EmbedSignDocumentV1ClientPage } from '~/components/embed/embed-document-signing-page-v1';
@@ -78,6 +79,17 @@ async function handleV1Loader({ params, request }: Route.LoaderArgs) {
     );
   }
 
+  if (isRecipientExpired(recipient)) {
+    throw data(
+      {
+        type: 'embed-recipient-expired',
+      },
+      {
+        status: 403,
+      },
+    );
+  }
+
   const { derivedRecipientAccessAuth } = extractDocumentAuthMethods({
     documentAuth: document.authOptions,
   });
@@ -190,7 +202,7 @@ async function handleV2Loader({ params, request }: Route.LoaderArgs) {
     );
   }
 
-  const { envelope, recipient, isRecipientsTurn } = envelopeForSigning;
+  const { envelope, recipient, isRecipientsTurn, isExpired } = envelopeForSigning;
 
   const organisationClaim = await getOrganisationClaimByTeamId({ teamId: envelope.teamId });
 
@@ -208,6 +220,17 @@ async function handleV2Loader({ params, request }: Route.LoaderArgs) {
     );
   }
 
+  if (isExpired) {
+    throw data(
+      {
+        type: 'embed-recipient-expired',
+      },
+      {
+        status: 403,
+      },
+    );
+  }
+
   if (!isRecipientsTurn) {
     throw data(
       {
diff --git a/apps/remix/server/router.ts b/apps/remix/server/router.ts
index 037abcaf6..dd0eca8a9 100644
--- a/apps/remix/server/router.ts
+++ b/apps/remix/server/router.ts
@@ -86,6 +86,7 @@ app.use(async (c, next) => {
 
   const honoLogger = logger.child({
     requestId: c.var.requestId,
+    requestPath: c.req.path,
     ipAddress: metadata.ipAddress,
     userAgent: metadata.userAgent,
   });
@@ -146,6 +147,10 @@ if (env('NODE_ENV') !== 'development') {
 // Start license client to verify license on startup.
 void LicenseClient.start();
 
+// Start cron scheduler for background jobs (e.g. envelope expiration sweep).
+// No-op for Inngest provider which handles cron externally.
+jobsClient.startCron();
+
 void migrateDeletedAccountServiceAccount();
 void migrateLegacyServiceAccount();
 
diff --git a/package-lock.json b/package-lock.json
index 4906e375d..389f17010 100644
--- a/package-lock.json
+++ b/package-lock.json
@@ -19,6 +19,7 @@
         "@lingui/conf": "^5.6.0",
         "@lingui/core": "^5.6.0",
         "ai": "^5.0.104",
+        "cron-parser": "^5.5.0",
         "luxon": "^3.7.2",
         "patch-package": "^8.0.1",
         "posthog-node": "4.18.0",
@@ -20192,6 +20193,18 @@
         "typescript": ">=5"
       }
     },
+    "node_modules/cron-parser": {
+      "version": "5.5.0",
+      "resolved": "https://registry.npmjs.org/cron-parser/-/cron-parser-5.5.0.tgz",
+      "integrity": "sha512-oML4lKUXxizYswqmxuOCpgFS8BNUJpIu6k/2HVHyaL8Ynnf3wdf9tkns0yRdJLSIjkJ+b0DXHMZEHGpMwjnPww==",
+      "license": "MIT",
+      "dependencies": {
+        "luxon": "^3.7.1"
+      },
+      "engines": {
+        "node": ">=18"
+      }
+    },
     "node_modules/cross-env": {
       "version": "10.1.0",
       "resolved": "https://registry.npmjs.org/cross-env/-/cross-env-10.1.0.tgz",
diff --git a/package.json b/package.json
index 254bb8652..5a2bfeae3 100644
--- a/package.json
+++ b/package.json
@@ -90,6 +90,7 @@
     "@lingui/conf": "^5.6.0",
     "@lingui/core": "^5.6.0",
     "ai": "^5.0.104",
+    "cron-parser": "^5.5.0",
     "luxon": "^3.7.2",
     "patch-package": "^8.0.1",
     "posthog-node": "4.18.0",
diff --git a/packages/api/v1/schema.ts b/packages/api/v1/schema.ts
index 6b2cbc65c..58ad056bf 100644
--- a/packages/api/v1/schema.ts
+++ b/packages/api/v1/schema.ts
@@ -437,8 +437,8 @@ export const ZSuccessfulRecipientResponseSchema = z.object({
   role: z.nativeEnum(RecipientRole),
   signingOrder: z.number().nullish(),
   token: z.string(),
-  // !: Not used for now
-  // expired: z.string(),
+  expiresAt: z.date().nullish(),
+  expirationNotifiedAt: z.date().nullish(),
   signedAt: z.date().nullable(),
   readStatus: z.nativeEnum(ReadStatus),
   signingStatus: z.nativeEnum(SigningStatus),
@@ -576,7 +576,8 @@ export const ZRecipientSchema = z.object({
   token: z.string(),
   signingOrder: z.number().nullish(),
   documentDeletedAt: z.date().nullish(),
-  expired: z.date().nullish(),
+  expiresAt: z.date().nullish(),
+  expirationNotifiedAt: z.date().nullish(),
   signedAt: z.date().nullish(),
   authOptions: z.unknown(),
   role: z.nativeEnum(RecipientRole),
diff --git a/packages/app-tests/e2e/api/v2/envelopes-api.spec.ts b/packages/app-tests/e2e/api/v2/envelopes-api.spec.ts
index beac50e56..ffabac913 100644
--- a/packages/app-tests/e2e/api/v2/envelopes-api.spec.ts
+++ b/packages/app-tests/e2e/api/v2/envelopes-api.spec.ts
@@ -171,6 +171,7 @@ test.describe('API V2 Envelopes', () => {
                 positionY: 0,
                 width: 0,
                 height: 0,
+                fieldMeta: { type: 'signature' },
               },
               {
                 type: FieldType.SIGNATURE,
@@ -180,6 +181,7 @@ test.describe('API V2 Envelopes', () => {
                 positionY: 0,
                 width: 0,
                 height: 0,
+                fieldMeta: { type: 'signature' },
               },
             ],
           },
@@ -205,6 +207,7 @@ test.describe('API V2 Envelopes', () => {
             documentPending: false,
             documentCompleted: false,
             documentDeleted: false,
+            ownerRecipientExpired: true,
             ownerDocumentCompleted: true,
           },
         },
diff --git a/packages/app-tests/e2e/envelopes/envelope-expiration-send.spec.ts b/packages/app-tests/e2e/envelopes/envelope-expiration-send.spec.ts
new file mode 100644
index 000000000..8610a59e2
--- /dev/null
+++ b/packages/app-tests/e2e/envelopes/envelope-expiration-send.spec.ts
@@ -0,0 +1,291 @@
+import { expect, test } from '@playwright/test';
+import fs from 'node:fs';
+import path from 'node:path';
+
+import { NEXT_PUBLIC_WEBAPP_URL } from '@documenso/lib/constants/app';
+import { createApiToken } from '@documenso/lib/server-only/public-api/create-api-token';
+import { prisma } from '@documenso/prisma';
+import { EnvelopeType, RecipientRole } from '@documenso/prisma/client';
+import { seedPendingDocument } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+import type {
+  TCreateEnvelopePayload,
+  TCreateEnvelopeResponse,
+} from '@documenso/trpc/server/envelope-router/create-envelope.types';
+import type { TDistributeEnvelopeRequest } from '@documenso/trpc/server/envelope-router/distribute-envelope.types';
+
+import { apiSignin } from '../fixtures/authentication';
+import { openDropdownMenu } from '../fixtures/generic';
+
+const WEBAPP_BASE_URL = NEXT_PUBLIC_WEBAPP_URL();
+const baseUrl = `${WEBAPP_BASE_URL}/api/v2-beta`;
+
+const examplePdf = fs.readFileSync(path.join(__dirname, '../../../../assets/example.pdf'));
+
+test.describe.configure({ mode: 'parallel' });
+
+test('[ENVELOPE_EXPIRATION]: sending document sets expiresAt on recipients', async ({
+  request,
+}) => {
+  const { user, team } = await seedUser();
+
+  const { token } = await createApiToken({
+    userId: user.id,
+    teamId: team.id,
+    tokenName: 'test-expiration-send',
+    expiresIn: null,
+  });
+
+  const createPayload: TCreateEnvelopePayload = {
+    type: EnvelopeType.DOCUMENT,
+    title: '[TEST] Expiration Send Test',
+    recipients: [
+      {
+        email: 'signer-expiry@test.documenso.com',
+        name: 'Signer Expiry',
+        role: RecipientRole.SIGNER,
+        fields: [
+          {
+            type: 'SIGNATURE',
+            page: 1,
+            positionX: 10,
+            positionY: 10,
+            width: 10,
+            height: 5,
+            fieldMeta: { type: 'signature' },
+          },
+        ],
+      },
+    ],
+  };
+
+  const formData = new FormData();
+  formData.append('payload', JSON.stringify(createPayload));
+  formData.append('files', new File([examplePdf], 'example.pdf', { type: 'application/pdf' }));
+
+  const createRes = await request.post(`${baseUrl}/envelope/create`, {
+    headers: { Authorization: `Bearer ${token}` },
+    multipart: formData,
+  });
+
+  expect(createRes.ok()).toBeTruthy();
+
+  const { id: envelopeId }: TCreateEnvelopeResponse = await createRes.json();
+
+  const distributeRes = await request.post(`${baseUrl}/envelope/distribute`, {
+    headers: { Authorization: `Bearer ${token}` },
+    data: { envelopeId } satisfies TDistributeEnvelopeRequest,
+  });
+
+  expect(distributeRes.ok()).toBeTruthy();
+
+  // Check that recipients now have expiresAt set.
+  const recipients = await prisma.recipient.findMany({
+    where: { envelopeId },
+  });
+
+  expect(recipients.length).toBe(1);
+  expect(recipients[0].expiresAt).not.toBeNull();
+
+  // The default expiration period is 3 months. Verify it's roughly correct.
+  const expiresAt = recipients[0].expiresAt!;
+  const now = new Date();
+  const diffMs = expiresAt.getTime() - now.getTime();
+  const diffDays = diffMs / (1000 * 60 * 60 * 24);
+
+  // 3 months is roughly 89-92 days. Allow a generous range.
+  expect(diffDays).toBeGreaterThan(80);
+  expect(diffDays).toBeLessThan(100);
+});
+
+test('[ENVELOPE_EXPIRATION]: sending document with custom org expiration period', async ({
+  request,
+}) => {
+  const { user, organisation, team } = await seedUser();
+
+  // Set org expiration to 7 days.
+  await prisma.organisationGlobalSettings.update({
+    where: { id: organisation.organisationGlobalSettingsId },
+    data: { envelopeExpirationPeriod: { unit: 'day', amount: 7 } },
+  });
+
+  const { token } = await createApiToken({
+    userId: user.id,
+    teamId: team.id,
+    tokenName: 'test-expiration-custom',
+    expiresIn: null,
+  });
+
+  const createPayload: TCreateEnvelopePayload = {
+    type: EnvelopeType.DOCUMENT,
+    title: '[TEST] Custom Expiration Send Test',
+    recipients: [
+      {
+        email: 'signer-custom@test.documenso.com',
+        name: 'Signer Custom',
+        role: RecipientRole.SIGNER,
+        fields: [
+          {
+            type: 'SIGNATURE',
+            page: 1,
+            positionX: 10,
+            positionY: 10,
+            width: 10,
+            height: 5,
+            fieldMeta: { type: 'signature' },
+          },
+        ],
+      },
+    ],
+  };
+
+  const formData = new FormData();
+  formData.append('payload', JSON.stringify(createPayload));
+  formData.append('files', new File([examplePdf], 'example.pdf', { type: 'application/pdf' }));
+
+  const createRes = await request.post(`${baseUrl}/envelope/create`, {
+    headers: { Authorization: `Bearer ${token}` },
+    multipart: formData,
+  });
+
+  expect(createRes.ok()).toBeTruthy();
+
+  const { id: envelopeId }: TCreateEnvelopeResponse = await createRes.json();
+
+  const distributeRes = await request.post(`${baseUrl}/envelope/distribute`, {
+    headers: { Authorization: `Bearer ${token}` },
+    data: { envelopeId } satisfies TDistributeEnvelopeRequest,
+  });
+
+  expect(distributeRes.ok()).toBeTruthy();
+
+  const recipients = await prisma.recipient.findMany({
+    where: { envelopeId },
+  });
+
+  expect(recipients.length).toBe(1);
+  expect(recipients[0].expiresAt).not.toBeNull();
+
+  // 7 days expiration.
+  const expiresAt = recipients[0].expiresAt!;
+  const now = new Date();
+  const diffMs = expiresAt.getTime() - now.getTime();
+  const diffDays = diffMs / (1000 * 60 * 60 * 24);
+
+  expect(diffDays).toBeGreaterThan(6);
+  expect(diffDays).toBeLessThan(8);
+});
+
+test('[ENVELOPE_EXPIRATION]: sending document with expiration disabled', async ({ request }) => {
+  const { user, organisation, team } = await seedUser();
+
+  // Disable expiration at org level.
+  await prisma.organisationGlobalSettings.update({
+    where: { id: organisation.organisationGlobalSettingsId },
+    data: { envelopeExpirationPeriod: { disabled: true } },
+  });
+
+  const { token } = await createApiToken({
+    userId: user.id,
+    teamId: team.id,
+    tokenName: 'test-expiration-disabled',
+    expiresIn: null,
+  });
+
+  const createPayload: TCreateEnvelopePayload = {
+    type: EnvelopeType.DOCUMENT,
+    title: '[TEST] Disabled Expiration Send Test',
+    recipients: [
+      {
+        email: 'signer-disabled@test.documenso.com',
+        name: 'Signer Disabled',
+        role: RecipientRole.SIGNER,
+        fields: [
+          {
+            type: 'SIGNATURE',
+            page: 1,
+            positionX: 10,
+            positionY: 10,
+            width: 10,
+            height: 5,
+            fieldMeta: { type: 'signature' },
+          },
+        ],
+      },
+    ],
+  };
+
+  const formData = new FormData();
+  formData.append('payload', JSON.stringify(createPayload));
+  formData.append('files', new File([examplePdf], 'example.pdf', { type: 'application/pdf' }));
+
+  const createRes = await request.post(`${baseUrl}/envelope/create`, {
+    headers: { Authorization: `Bearer ${token}` },
+    multipart: formData,
+  });
+
+  expect(createRes.ok()).toBeTruthy();
+
+  const { id: envelopeId }: TCreateEnvelopeResponse = await createRes.json();
+
+  const distributeRes = await request.post(`${baseUrl}/envelope/distribute`, {
+    headers: { Authorization: `Bearer ${token}` },
+    data: { envelopeId } satisfies TDistributeEnvelopeRequest,
+  });
+
+  expect(distributeRes.ok()).toBeTruthy();
+
+  const recipients = await prisma.recipient.findMany({
+    where: { envelopeId },
+  });
+
+  expect(recipients.length).toBe(1);
+  expect(recipients[0].expiresAt).toBeNull();
+});
+
+test('[ENVELOPE_EXPIRATION]: resending refreshes expiresAt', async ({ page }) => {
+  const { user, team } = await seedUser();
+
+  const document = await seedPendingDocument(user, team.id, ['resend-target@test.documenso.com']);
+
+  const recipient = document.recipients[0];
+
+  // Set an initial expiresAt that's 1 day from now.
+  const initialExpiresAt = new Date(Date.now() + 24 * 60 * 60 * 1000);
+
+  await prisma.recipient.update({
+    where: { id: recipient.id },
+    data: { expiresAt: initialExpiresAt },
+  });
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/t/${team.url}/documents?status=PENDING`,
+  });
+
+  // Open the document action menu and click Resend.
+  const actionBtn = page.getByTestId('document-table-action-btn').first();
+  await expect(actionBtn).toBeAttached();
+  await openDropdownMenu(page, actionBtn);
+  await expect(page.getByRole('menuitem', { name: 'Resend' })).toBeVisible();
+  await page.getByRole('menuitem', { name: 'Resend' }).click();
+
+  // Select the recipient and send.
+  await page.getByLabel('test.documenso.com').first().click();
+  await page.getByRole('button', { name: 'Send reminder' }).click();
+
+  await expect(page.getByText('Document re-sent', { exact: true })).toBeVisible({
+    timeout: 10_000,
+  });
+
+  // Verify expiresAt was refreshed.
+  await expect(async () => {
+    const updatedRecipient = await prisma.recipient.findUniqueOrThrow({
+      where: { id: recipient.id },
+    });
+
+    expect(updatedRecipient.expiresAt).not.toBeNull();
+    expect(updatedRecipient.expiresAt!.getTime()).toBeGreaterThan(initialExpiresAt.getTime());
+  }).toPass({ timeout: 10_000 });
+});
diff --git a/packages/app-tests/e2e/envelopes/envelope-expiration-settings.spec.ts b/packages/app-tests/e2e/envelopes/envelope-expiration-settings.spec.ts
new file mode 100644
index 000000000..7710a3ddb
--- /dev/null
+++ b/packages/app-tests/e2e/envelopes/envelope-expiration-settings.spec.ts
@@ -0,0 +1,150 @@
+import { expect, test } from '@playwright/test';
+
+import { getTeamSettings } from '@documenso/lib/server-only/team/get-team-settings';
+import { prisma } from '@documenso/prisma';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+
+test.describe.configure({ mode: 'parallel' });
+
+test('[ENVELOPE_EXPIRATION]: set custom expiration period at organisation level', async ({
+  page,
+}) => {
+  const { user, organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/o/${organisation.url}/settings/document`,
+  });
+
+  // Wait for the form to load.
+  await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
+
+  // Change the amount to 2.
+  const amountInput = page.getByRole('spinbutton');
+  await amountInput.clear();
+  await amountInput.fill('2');
+
+  // Find all triggers, the unit picker is the one showing Months/Days/etc.
+  // In the duration mode, there's a mode select and a unit select.
+  // The unit select is inside the duration row, after the number input.
+  // Let's find the select trigger that contains the unit text.
+  const unitTrigger = page
+    .locator('button[role="combobox"]')
+    .filter({ hasText: /Months|Days|Weeks|Years/ });
+
+  await unitTrigger.click();
+  await page.getByRole('option', { name: 'Weeks' }).click();
+
+  await page.getByRole('button', { name: 'Update' }).first().click();
+  await expect(page.getByText('Your document preferences have been updated').first()).toBeVisible();
+
+  // Verify via database.
+  const orgSettings = await prisma.organisationGlobalSettings.findUniqueOrThrow({
+    where: { id: organisation.organisationGlobalSettingsId },
+  });
+
+  expect(orgSettings.envelopeExpirationPeriod).toEqual({ unit: 'week', amount: 2 });
+});
+
+test('[ENVELOPE_EXPIRATION]: disable expiration at organisation level', async ({ page }) => {
+  const { user, organisation } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/o/${organisation.url}/settings/document`,
+  });
+
+  await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
+
+  // Find the mode select (shows "Custom duration") and change to "Never expires".
+  const modeTrigger = page
+    .locator('button[role="combobox"]')
+    .filter({ hasText: 'Custom duration' });
+  await modeTrigger.click();
+  await page.getByRole('option', { name: 'Never expires' }).click();
+
+  await page.getByRole('button', { name: 'Update' }).first().click();
+  await expect(page.getByText('Your document preferences have been updated').first()).toBeVisible();
+
+  // Verify via database.
+  const orgSettings = await prisma.organisationGlobalSettings.findUniqueOrThrow({
+    where: { id: organisation.organisationGlobalSettingsId },
+  });
+
+  expect(orgSettings.envelopeExpirationPeriod).toEqual({ disabled: true });
+});
+
+test('[ENVELOPE_EXPIRATION]: team inherits expiration from organisation', async () => {
+  const { organisation, team } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  // Set org expiration to 2 weeks directly.
+  await prisma.organisationGlobalSettings.update({
+    where: { id: organisation.organisationGlobalSettingsId },
+    data: { envelopeExpirationPeriod: { unit: 'week', amount: 2 } },
+  });
+
+  // Verify team settings inherit the org setting.
+  const teamSettings = await getTeamSettings({ teamId: team.id });
+
+  expect(teamSettings.envelopeExpirationPeriod).toEqual({ unit: 'week', amount: 2 });
+});
+
+test('[ENVELOPE_EXPIRATION]: team overrides organisation expiration', async ({ page }) => {
+  const { user, organisation, team } = await seedUser({
+    isPersonalOrganisation: false,
+  });
+
+  // Set org expiration to 2 weeks.
+  await prisma.organisationGlobalSettings.update({
+    where: { id: organisation.organisationGlobalSettingsId },
+    data: { envelopeExpirationPeriod: { unit: 'week', amount: 2 } },
+  });
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/t/${team.url}/settings/document`,
+  });
+
+  await expect(page.getByRole('button', { name: 'Update' }).first()).toBeVisible();
+
+  // Scope to the "Default Envelope Expiration" form field section.
+  const expirationSection = page.getByText('Default Envelope Expiration').locator('..');
+
+  // The expiration picker mode select should show "Inherit from organisation" by default.
+  const modeTrigger = expirationSection.locator('button[role="combobox"]').first();
+  await expect(modeTrigger).toBeVisible();
+
+  // Switch to custom duration.
+  await modeTrigger.click();
+  await page.getByRole('option', { name: 'Custom duration' }).click();
+
+  // Set to 5 days.
+  const amountInput = expirationSection.getByRole('spinbutton');
+  await amountInput.clear();
+  await amountInput.fill('5');
+
+  const unitTrigger = expirationSection
+    .locator('button[role="combobox"]')
+    .filter({ hasText: /Months|Days|Weeks|Years/ });
+  await unitTrigger.click();
+  await page.getByRole('option', { name: 'Days' }).click();
+
+  await page.getByRole('button', { name: 'Update' }).first().click();
+  await expect(page.getByText('Your document preferences have been updated').first()).toBeVisible();
+
+  // Verify team setting is overridden.
+  const teamSettings = await getTeamSettings({ teamId: team.id });
+
+  expect(teamSettings.envelopeExpirationPeriod).toEqual({ unit: 'day', amount: 5 });
+});
diff --git a/packages/app-tests/e2e/envelopes/envelope-expiration-signing.spec.ts b/packages/app-tests/e2e/envelopes/envelope-expiration-signing.spec.ts
new file mode 100644
index 000000000..873229288
--- /dev/null
+++ b/packages/app-tests/e2e/envelopes/envelope-expiration-signing.spec.ts
@@ -0,0 +1,131 @@
+import { expect, test } from '@playwright/test';
+
+import { prisma } from '@documenso/prisma';
+import { FieldType } from '@documenso/prisma/client';
+import { seedPendingDocumentWithFullFields } from '@documenso/prisma/seed/documents';
+import { seedUser } from '@documenso/prisma/seed/users';
+
+import { apiSignin } from '../fixtures/authentication';
+import { signSignaturePad } from '../fixtures/signature';
+
+test.describe.configure({ mode: 'parallel' });
+
+test('[ENVELOPE_EXPIRATION]: expired recipient is redirected to expired page', async ({ page }) => {
+  const { user, team } = await seedUser();
+
+  const { recipients } = await seedPendingDocumentWithFullFields({
+    owner: user,
+    recipients: ['expired-recipient@test.documenso.com'],
+    teamId: team.id,
+  });
+
+  const recipient = recipients[0];
+
+  // Set expiresAt to the past so the recipient is expired.
+  await prisma.recipient.update({
+    where: { id: recipient.id },
+    data: { expiresAt: new Date(Date.now() - 60_000) },
+  });
+
+  await page.goto(`/sign/${recipient.token}`);
+  await page.waitForURL(`/sign/${recipient.token}/expired`);
+
+  await expect(page.getByText('Signing Deadline Expired')).toBeVisible();
+  await expect(page.getByText('The signing deadline for this document has passed')).toBeVisible();
+});
+
+test('[ENVELOPE_EXPIRATION]: non-expired recipient can access signing page', async ({ page }) => {
+  const { user, team } = await seedUser();
+
+  const { recipients } = await seedPendingDocumentWithFullFields({
+    owner: user,
+    recipients: ['active-recipient@test.documenso.com'],
+    teamId: team.id,
+  });
+
+  const recipient = recipients[0];
+
+  // Set expiresAt to 1 hour in the future.
+  await prisma.recipient.update({
+    where: { id: recipient.id },
+    data: { expiresAt: new Date(Date.now() + 60 * 60 * 1000) },
+  });
+
+  await page.goto(`/sign/${recipient.token}`);
+
+  await expect(page.getByRole('heading', { name: 'Sign Document' })).toBeVisible();
+});
+
+test('[ENVELOPE_EXPIRATION]: recipient with null expiresAt can sign normally', async ({ page }) => {
+  const { user, team } = await seedUser();
+
+  const { recipients } = await seedPendingDocumentWithFullFields({
+    owner: user,
+    recipients: ['null-expiry@test.documenso.com'],
+    teamId: team.id,
+  });
+
+  const recipient = recipients[0];
+
+  // Verify expiresAt is null (default from seed).
+  const dbRecipient = await prisma.recipient.findUniqueOrThrow({
+    where: { id: recipient.id },
+  });
+
+  expect(dbRecipient.expiresAt).toBeNull();
+
+  await page.goto(`/sign/${recipient.token}`);
+
+  await expect(page.getByRole('heading', { name: 'Sign Document' })).toBeVisible();
+});
+
+test('[ENVELOPE_EXPIRATION]: expired recipient cannot complete signing', async ({ page }) => {
+  const { user, team } = await seedUser();
+
+  // Use only a SIGNATURE field to simplify the signing flow.
+  const { recipients } = await seedPendingDocumentWithFullFields({
+    owner: user,
+    recipients: [user],
+    teamId: team.id,
+    fields: [FieldType.SIGNATURE],
+  });
+
+  const recipient = recipients[0];
+
+  await apiSignin({
+    page,
+    email: user.email,
+    redirectPath: `/sign/${recipient.token}`,
+  });
+
+  await expect(page.getByRole('heading', { name: 'Sign Document' })).toBeVisible();
+
+  // Now expire the recipient while they're on the signing page.
+  await prisma.recipient.update({
+    where: { id: recipient.id },
+    data: { expiresAt: new Date(Date.now() - 1_000) },
+  });
+
+  // Set up signature.
+  await signSignaturePad(page);
+
+  // Click the signature field to attempt to insert it.
+  // The server will reject because the recipient is now expired.
+  const signatureField = recipient.fields.find((f) => f.type === FieldType.SIGNATURE);
+
+  if (signatureField) {
+    await page.locator(`#field-${signatureField.id}`).getByRole('button').click();
+  }
+
+  // The server should reject the signing attempt because the recipient has expired.
+  // Verify the field was NOT inserted (stays data-inserted="false").
+  if (signatureField) {
+    await expect(async () => {
+      const field = await prisma.field.findUniqueOrThrow({
+        where: { id: signatureField.id },
+      });
+
+      expect(field.inserted).toBe(false);
+    }).toPass({ timeout: 10_000 });
+  }
+});
diff --git a/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts b/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
index 400f635ba..abb2a08d6 100644
--- a/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
+++ b/packages/app-tests/e2e/organisations/organisation-team-preferences.spec.ts
@@ -229,6 +229,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
     documentPending: false, // unchecked
     documentCompleted: true,
     documentDeleted: false, // unchecked
+    ownerRecipientExpired: true,
     ownerDocumentCompleted: true,
   });
 
@@ -244,9 +245,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
   await page.getByRole('option', { name: 'Override organisation settings' }).click();
 
   // Update some email settings
-  await page
-    .getByRole('checkbox', { name: 'Email recipients with a signing request' })
-    .uncheck();
+  await page.getByRole('checkbox', { name: 'Email recipients with a signing request' }).uncheck();
   await page
     .getByRole('checkbox', { name: 'Email recipients when the document is completed', exact: true })
     .uncheck();
@@ -270,6 +269,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
     documentPending: true,
     documentCompleted: false,
     documentDeleted: true,
+    ownerRecipientExpired: true,
     ownerDocumentCompleted: false,
   });
 
@@ -290,6 +290,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
     documentPending: true,
     documentCompleted: false,
     documentDeleted: true,
+    ownerRecipientExpired: true,
     ownerDocumentCompleted: false,
   });
 
@@ -315,6 +316,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
     documentPending: false,
     documentCompleted: true,
     documentDeleted: false,
+    ownerRecipientExpired: true,
     ownerDocumentCompleted: true,
   });
 
@@ -335,6 +337,7 @@ test('[ORGANISATIONS]: manage email preferences', async ({ page }) => {
     documentPending: false,
     documentCompleted: true,
     documentDeleted: false,
+    ownerRecipientExpired: true,
     ownerDocumentCompleted: true,
   });
 });
diff --git a/packages/email/template-components/template-recipient-expired.tsx b/packages/email/template-components/template-recipient-expired.tsx
new file mode 100644
index 000000000..9df723a2f
--- /dev/null
+++ b/packages/email/template-components/template-recipient-expired.tsx
@@ -0,0 +1,54 @@
+import { Trans } from '@lingui/react/macro';
+
+import { Button, Section, Text } from '../components';
+import { TemplateDocumentImage } from './template-document-image';
+
+export type TemplateRecipientExpiredProps = {
+  documentName: string;
+  recipientName: string;
+  recipientEmail: string;
+  documentLink: string;
+  assetBaseUrl: string;
+};
+
+export const TemplateRecipientExpired = ({
+  documentName,
+  recipientName,
+  recipientEmail,
+  documentLink,
+  assetBaseUrl,
+}: TemplateRecipientExpiredProps) => {
+  const displayName = recipientName || recipientEmail;
+
+  return (
+    <>
+      <TemplateDocumentImage className="mt-6" assetBaseUrl={assetBaseUrl} />
+
+      <Section>
+        <Text className="mx-auto mb-0 max-w-[80%] text-center text-lg font-semibold text-primary">
+          <Trans>
+            Signing window expired for "{displayName}" on "{documentName}"
+          </Trans>
+        </Text>
+
+        <Text className="my-1 text-center text-base text-slate-400">
+          <Trans>
+            The signing window for {displayName} on document "{documentName}" has expired. You can
+            resend the document to extend their deadline or cancel the document.
+          </Trans>
+        </Text>
+
+        <Section className="my-4 text-center">
+          <Button
+            className="inline-flex items-center justify-center rounded-lg bg-documenso-500 px-6 py-3 text-center text-sm font-medium text-white no-underline"
+            href={documentLink}
+          >
+            <Trans>View Document</Trans>
+          </Button>
+        </Section>
+      </Section>
+    </>
+  );
+};
+
+export default TemplateRecipientExpired;
diff --git a/packages/email/templates/recipient-expired.tsx b/packages/email/templates/recipient-expired.tsx
new file mode 100644
index 000000000..4e39c4dfa
--- /dev/null
+++ b/packages/email/templates/recipient-expired.tsx
@@ -0,0 +1,68 @@
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+
+import { Body, Container, Head, Hr, Html, Img, Preview, Section } from '../components';
+import { useBranding } from '../providers/branding';
+import { TemplateFooter } from '../template-components/template-footer';
+import type { TemplateRecipientExpiredProps } from '../template-components/template-recipient-expired';
+import { TemplateRecipientExpired } from '../template-components/template-recipient-expired';
+
+export type RecipientExpiredEmailTemplateProps = Partial<TemplateRecipientExpiredProps>;
+
+export const RecipientExpiredTemplate = ({
+  documentName = 'Open Source Pledge.pdf',
+  recipientName = 'John Doe',
+  recipientEmail = 'john@example.com',
+  documentLink = 'https://documenso.com',
+  assetBaseUrl = 'http://localhost:3002',
+}: RecipientExpiredEmailTemplateProps) => {
+  const { _ } = useLingui();
+  const branding = useBranding();
+
+  const previewText = msg`The signing window for "${recipientName}" on document "${documentName}" has expired.`;
+
+  const getAssetUrl = (path: string) => {
+    return new URL(path, assetBaseUrl).toString();
+  };
+
+  return (
+    <Html>
+      <Head />
+      <Preview>{_(previewText)}</Preview>
+
+      <Body className="mx-auto my-auto bg-white font-sans">
+        <Section>
+          <Container className="mx-auto mb-2 mt-8 max-w-xl rounded-lg border border-solid border-slate-200 p-4 backdrop-blur-sm">
+            <Section>
+              {branding.brandingEnabled && branding.brandingLogo ? (
+                <Img src={branding.brandingLogo} alt="Branding Logo" className="mb-4 h-6" />
+              ) : (
+                <Img
+                  src={getAssetUrl('/static/logo.png')}
+                  alt="Documenso Logo"
+                  className="mb-4 h-6"
+                />
+              )}
+
+              <TemplateRecipientExpired
+                documentName={documentName}
+                recipientName={recipientName}
+                recipientEmail={recipientEmail}
+                documentLink={documentLink}
+                assetBaseUrl={assetBaseUrl}
+              />
+            </Section>
+          </Container>
+
+          <Hr className="mx-auto mt-12 max-w-xl" />
+
+          <Container className="mx-auto max-w-xl">
+            <TemplateFooter />
+          </Container>
+        </Section>
+      </Body>
+    </Html>
+  );
+};
+
+export default RecipientExpiredTemplate;
diff --git a/packages/lib/constants/envelope-expiration.ts b/packages/lib/constants/envelope-expiration.ts
new file mode 100644
index 000000000..212872b27
--- /dev/null
+++ b/packages/lib/constants/envelope-expiration.ts
@@ -0,0 +1,66 @@
+import type { DurationLikeObject } from 'luxon';
+import { Duration } from 'luxon';
+import { z } from 'zod';
+
+export const ZEnvelopeExpirationDurationPeriod = z.object({
+  unit: z.enum(['day', 'week', 'month', 'year']),
+  amount: z.number().int().min(1),
+});
+
+export const ZEnvelopeExpirationDisabledPeriod = z.object({
+  disabled: z.literal(true),
+});
+
+export const ZEnvelopeExpirationPeriod = z.union([
+  ZEnvelopeExpirationDurationPeriod,
+  ZEnvelopeExpirationDisabledPeriod,
+]);
+
+export type TEnvelopeExpirationPeriod = z.infer<typeof ZEnvelopeExpirationPeriod>;
+export type TEnvelopeExpirationDurationPeriod = z.infer<typeof ZEnvelopeExpirationDurationPeriod>;
+
+const UNIT_TO_LUXON_KEY: Record<
+  TEnvelopeExpirationDurationPeriod['unit'],
+  keyof DurationLikeObject
+> = {
+  day: 'days',
+  week: 'weeks',
+  month: 'months',
+  year: 'years',
+};
+
+export const DEFAULT_ENVELOPE_EXPIRATION_PERIOD: TEnvelopeExpirationDurationPeriod = {
+  unit: 'month',
+  amount: 3,
+};
+
+export const getEnvelopeExpirationDuration = (
+  period: TEnvelopeExpirationDurationPeriod,
+): Duration => {
+  return Duration.fromObject({ [UNIT_TO_LUXON_KEY[period.unit]]: period.amount });
+};
+
+/**
+ * Resolve the concrete expiresAt timestamp from a raw expiration period (from JSON column).
+ *
+ * - `null` means use the default period (3 months).
+ * - `{ disabled: true }` means never expires (returns null).
+ * - `{ unit, amount }` means compute the timestamp from now + duration.
+ */
+export const resolveExpiresAt = (rawPeriod: unknown): Date | null => {
+  if (rawPeriod === null || rawPeriod === undefined) {
+    const duration = getEnvelopeExpirationDuration(DEFAULT_ENVELOPE_EXPIRATION_PERIOD);
+
+    return new Date(Date.now() + duration.toMillis());
+  }
+
+  const parsed = ZEnvelopeExpirationPeriod.parse(rawPeriod);
+
+  if ('disabled' in parsed) {
+    return null;
+  }
+
+  const duration = getEnvelopeExpirationDuration(parsed);
+
+  return new Date(Date.now() + duration.toMillis());
+};
diff --git a/packages/lib/errors/app-error.ts b/packages/lib/errors/app-error.ts
index ee82bcd91..2ee4579f2 100644
--- a/packages/lib/errors/app-error.ts
+++ b/packages/lib/errors/app-error.ts
@@ -9,6 +9,7 @@ export enum AppErrorCode {
   'EXPIRED_CODE' = 'EXPIRED_CODE',
   'INVALID_BODY' = 'INVALID_BODY',
   'INVALID_REQUEST' = 'INVALID_REQUEST',
+  'RECIPIENT_EXPIRED' = 'RECIPIENT_EXPIRED',
   'LIMIT_EXCEEDED' = 'LIMIT_EXCEEDED',
   'NOT_FOUND' = 'NOT_FOUND',
   'NOT_SETUP' = 'NOT_SETUP',
@@ -23,6 +24,7 @@ export enum AppErrorCode {
 export const genericErrorCodeToTrpcErrorCodeMap: Record<string, { code: string; status: number }> =
   {
     [AppErrorCode.ALREADY_EXISTS]: { code: 'BAD_REQUEST', status: 400 },
+    [AppErrorCode.RECIPIENT_EXPIRED]: { code: 'BAD_REQUEST', status: 400 },
     [AppErrorCode.EXPIRED_CODE]: { code: 'BAD_REQUEST', status: 400 },
     [AppErrorCode.INVALID_BODY]: { code: 'BAD_REQUEST', status: 400 },
     [AppErrorCode.INVALID_REQUEST]: { code: 'BAD_REQUEST', status: 400 },
diff --git a/packages/lib/jobs/client.ts b/packages/lib/jobs/client.ts
index 857ed20cd..be699d6cd 100644
--- a/packages/lib/jobs/client.ts
+++ b/packages/lib/jobs/client.ts
@@ -3,6 +3,7 @@ import { SEND_CONFIRMATION_EMAIL_JOB_DEFINITION } from './definitions/emails/sen
 import { SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION } from './definitions/emails/send-document-cancelled-emails';
 import { SEND_ORGANISATION_MEMBER_JOINED_EMAIL_JOB_DEFINITION } from './definitions/emails/send-organisation-member-joined-email';
 import { SEND_ORGANISATION_MEMBER_LEFT_EMAIL_JOB_DEFINITION } from './definitions/emails/send-organisation-member-left-email';
+import { SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION } from './definitions/emails/send-owner-recipient-expired-email';
 import { SEND_PASSWORD_RESET_SUCCESS_EMAIL_JOB_DEFINITION } from './definitions/emails/send-password-reset-success-email';
 import { SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION } from './definitions/emails/send-recipient-signed-email';
 import { SEND_SIGNING_REJECTION_EMAILS_JOB_DEFINITION } from './definitions/emails/send-rejection-emails';
@@ -11,6 +12,8 @@ import { SEND_TEAM_DELETED_EMAIL_JOB_DEFINITION } from './definitions/emails/sen
 import { BACKPORT_SUBSCRIPTION_CLAIM_JOB_DEFINITION } from './definitions/internal/backport-subscription-claims';
 import { BULK_SEND_TEMPLATE_JOB_DEFINITION } from './definitions/internal/bulk-send-template';
 import { EXECUTE_WEBHOOK_JOB_DEFINITION } from './definitions/internal/execute-webhook';
+import { EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION } from './definitions/internal/expire-recipients-sweep';
+import { PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION } from './definitions/internal/process-recipient-expired';
 import { SEAL_DOCUMENT_JOB_DEFINITION } from './definitions/internal/seal-document';
 
 /**
@@ -28,9 +31,12 @@ export const jobsClient = new JobClient([
   SEND_SIGNING_REJECTION_EMAILS_JOB_DEFINITION,
   SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION,
   SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION,
+  SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION,
   BACKPORT_SUBSCRIPTION_CLAIM_JOB_DEFINITION,
   BULK_SEND_TEMPLATE_JOB_DEFINITION,
   EXECUTE_WEBHOOK_JOB_DEFINITION,
+  EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION,
+  PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION,
 ] as const);
 
 export const jobs = jobsClient;
diff --git a/packages/lib/jobs/client/_internal/job.ts b/packages/lib/jobs/client/_internal/job.ts
index 426f1c251..68c464c6b 100644
--- a/packages/lib/jobs/client/_internal/job.ts
+++ b/packages/lib/jobs/client/_internal/job.ts
@@ -36,6 +36,11 @@ export type JobDefinition<Name extends string = string, Schema = any> = {
   trigger: {
     name: Name;
     schema?: z.ZodType<Schema>;
+    /**
+     * Optional cron expression (e.g., "* * * * *" for every minute).
+     * When set, the job runs on a schedule instead of being event-triggered.
+     */
+    cron?: string;
   };
   handler: (options: { payload: Schema; io: JobRunIO }) => Promise<Json | void>;
 };
diff --git a/packages/lib/jobs/client/base.ts b/packages/lib/jobs/client/base.ts
index 40ff7360d..53e66e0da 100644
--- a/packages/lib/jobs/client/base.ts
+++ b/packages/lib/jobs/client/base.ts
@@ -16,4 +16,14 @@ export abstract class BaseJobProvider {
   public getApiHandler(): (req: HonoContext) => Promise<Response | void> {
     throw new Error('Not implemented');
   }
+
+  /**
+   * Start the cron scheduler for any registered cron jobs.
+   *
+   * No-op for providers that handle cron scheduling externally (e.g. Inngest).
+   * Must be called explicitly at application startup.
+   */
+  public startCron(): void {
+    // No-op by default — providers override if needed.
+  }
 }
diff --git a/packages/lib/jobs/client/client.ts b/packages/lib/jobs/client/client.ts
index 8c9956e34..93ee0cd67 100644
--- a/packages/lib/jobs/client/client.ts
+++ b/packages/lib/jobs/client/client.ts
@@ -26,4 +26,15 @@ export class JobClient<T extends ReadonlyArray<JobDefinition> = []> {
   public getApiHandler() {
     return this._provider.getApiHandler();
   }
+
+  /**
+   * Start the cron scheduler for any registered cron jobs.
+   *
+   * Call this once at application startup after the instance is ready to
+   * process requests. No-op for providers that handle cron externally
+   * (e.g. Inngest).
+   */
+  public startCron() {
+    this._provider.startCron();
+  }
 }
diff --git a/packages/lib/jobs/client/inngest.ts b/packages/lib/jobs/client/inngest.ts
index 2a243e6c1..8b565342b 100644
--- a/packages/lib/jobs/client/inngest.ts
+++ b/packages/lib/jobs/client/inngest.ts
@@ -35,16 +35,17 @@ export class InngestJobProvider extends BaseJobProvider {
   }
 
   public defineJob<N extends string, T>(job: JobDefinition<N, T>): void {
-    console.log('defining job', job.id);
+    const triggerConfig: { cron: string } | { event: N } = job.trigger.cron
+      ? { cron: job.trigger.cron }
+      : { event: job.trigger.name };
+
     const fn = this._client.createFunction(
       {
         id: job.id,
         name: job.name,
         optimizeParallelism: job.optimizeParallelism ?? false,
       },
-      {
-        event: job.trigger.name,
-      },
+      triggerConfig,
       async (ctx) => {
         const io = this.convertInngestIoToJobRunIo(ctx);
 
diff --git a/packages/lib/jobs/client/local.ts b/packages/lib/jobs/client/local.ts
index 0540c137e..7c416d05a 100644
--- a/packages/lib/jobs/client/local.ts
+++ b/packages/lib/jobs/client/local.ts
@@ -1,5 +1,6 @@
-import { sha256 } from '@noble/hashes/sha256';
+import { sha256 } from '@noble/hashes/sha2';
 import { BackgroundJobStatus, Prisma } from '@prisma/client';
+import { CronExpressionParser } from 'cron-parser';
 import type { Context as HonoContext } from 'hono';
 
 import { prisma } from '@documenso/prisma';
@@ -16,10 +17,33 @@ import {
 import type { Json } from './_internal/json';
 import { BaseJobProvider } from './base';
 
+/**
+ * Build a deterministic BackgroundJob ID for a cron run so that multiple
+ * instances of the local provider racing to enqueue the same slot will
+ * collide on the primary key instead of creating duplicates.
+ */
+const createCronRunId = (jobId: string, scheduledFor: Date): string => {
+  const key = `cron:${jobId}:${scheduledFor.toISOString()}`;
+  const hash = Buffer.from(sha256(key)).toString('hex').slice(0, 24);
+
+  return `cron_${hash}`;
+};
+
+type CronJobEntry = {
+  definition: JobDefinition;
+  cron: string;
+  lastTickAt: Date;
+};
+
+const CRON_POLL_INTERVAL_MS = 30_000; // 30 seconds
+const CRON_POLL_JITTER_MS = 5_000; // 0-5 seconds random offset
+
 export class LocalJobProvider extends BaseJobProvider {
   private static _instance: LocalJobProvider;
 
   private _jobDefinitions: Record<string, JobDefinition> = {};
+  private _cronJobs: CronJobEntry[] = [];
+  private _cronPoller: NodeJS.Timeout | null = null;
 
   private constructor() {
     super();
@@ -38,6 +62,133 @@ export class LocalJobProvider extends BaseJobProvider {
       ...definition,
       enabled: definition.enabled ?? true,
     };
+
+    if (definition.trigger.cron && definition.enabled !== false) {
+      const alreadyRegistered = this._cronJobs.some((job) => job.definition.id === definition.id);
+
+      if (!alreadyRegistered) {
+        this._cronJobs.push({
+          definition: {
+            ...definition,
+            enabled: definition.enabled ?? true,
+          },
+          cron: definition.trigger.cron,
+          lastTickAt: new Date(),
+        });
+
+        console.log(`[JOBS]: Registered cron job ${definition.id} (${definition.trigger.cron})`);
+      }
+    }
+  }
+
+  /**
+   * Start the single cron poller for all registered cron jobs.
+   *
+   * Must be called explicitly at application startup after all jobs have been
+   * defined. The poller runs every 30 seconds (+ random jitter to avoid
+   * thundering herd across instances) and evaluates all registered cron jobs
+   * for due slots.
+   *
+   * For each due slot it creates a BackgroundJob row with a deterministic ID.
+   * If the insert succeeds the job is dispatched; if it fails with a unique
+   * constraint violation (P2002) another instance already claimed that slot.
+   */
+  public override startCron() {
+    if (this._cronPoller) {
+      return;
+    }
+
+    if (this._cronJobs.length === 0) {
+      return;
+    }
+
+    const tick = () => {
+      const jitter = Math.floor(Math.random() * CRON_POLL_JITTER_MS);
+
+      this._cronPoller = setTimeout(() => {
+        void this.processCronTick().finally(tick);
+      }, CRON_POLL_INTERVAL_MS + jitter);
+    };
+
+    tick();
+
+    console.log(`[JOBS]: Started cron poller for ${this._cronJobs.length} job(s)`);
+  }
+
+  private async processCronTick() {
+    for (const cronJob of this._cronJobs) {
+      try {
+        const dueSlots = this.getDueCronSlots(cronJob);
+
+        cronJob.lastTickAt = new Date();
+
+        if (dueSlots.length === 0) {
+          continue;
+        }
+
+        // Only take the latest slot — sweep-style jobs don't need to catch up
+        // every missed slot after downtime, just the most recent one.
+        const scheduledFor = dueSlots[dueSlots.length - 1];
+        const deterministicId = createCronRunId(cronJob.definition.id, scheduledFor);
+
+        const pendingJob = await prisma.backgroundJob
+          .create({
+            data: {
+              id: deterministicId,
+              jobId: cronJob.definition.id,
+              name: cronJob.definition.name,
+              version: cronJob.definition.version,
+              payload: { scheduledFor: scheduledFor.toISOString() },
+            },
+          })
+          .catch((error: unknown) => {
+            // P2002 = unique constraint violation — another instance already enqueued this slot.
+            if (error instanceof Prisma.PrismaClientKnownRequestError && error.code === 'P2002') {
+              return null;
+            }
+
+            throw error;
+          });
+
+        if (!pendingJob) {
+          continue;
+        }
+
+        await this.submitJobToEndpoint({
+          jobId: pendingJob.id,
+          jobDefinitionId: pendingJob.jobId,
+          data: {
+            name: cronJob.definition.trigger.name,
+            payload: { scheduledFor: scheduledFor.toISOString() },
+          },
+          isRetry: false,
+        });
+      } catch (error) {
+        console.error(`[JOBS]: Cron tick failed for ${cronJob.definition.id}`, error);
+      }
+    }
+  }
+
+  /**
+   * Use cron-parser to find all cron slots that are due between the last tick
+   * and now.
+   */
+  private getDueCronSlots(cronJob: CronJobEntry): Date[] {
+    const expr = CronExpressionParser.parse(cronJob.cron, {
+      currentDate: cronJob.lastTickAt,
+    });
+
+    const now = new Date();
+    const slots: Date[] = [];
+
+    let next = expr.next();
+
+    while (next.toDate() <= now) {
+      slots.push(next.toDate());
+      next = expr.next();
+    }
+
+    return slots;
   }
 
   public async triggerJob(options: SimpleTriggerJobOptions) {
diff --git a/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.handler.ts b/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.handler.ts
new file mode 100644
index 000000000..612823951
--- /dev/null
+++ b/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.handler.ts
@@ -0,0 +1,117 @@
+import { createElement } from 'react';
+
+import { msg } from '@lingui/core/macro';
+
+import { mailer } from '@documenso/email/mailer';
+import { RecipientExpiredTemplate } from '@documenso/email/templates/recipient-expired';
+import { prisma } from '@documenso/prisma';
+
+import { getI18nInstance } from '../../../client-only/providers/i18n-server';
+import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
+import { getEmailContext } from '../../../server-only/email/get-email-context';
+import { extractDerivedDocumentEmailSettings } from '../../../types/document-email';
+import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
+import { formatDocumentsPath } from '../../../utils/teams';
+import type { JobRunIO } from '../../client/_internal/job';
+import type { TSendOwnerRecipientExpiredEmailJobDefinition } from './send-owner-recipient-expired-email';
+
+export const run = async ({
+  payload,
+  io,
+}: {
+  payload: TSendOwnerRecipientExpiredEmailJobDefinition;
+  io: JobRunIO;
+}) => {
+  const { recipientId, envelopeId } = payload;
+
+  const envelope = await prisma.envelope.findFirst({
+    where: {
+      id: envelopeId,
+    },
+    include: {
+      user: {
+        select: {
+          id: true,
+          email: true,
+          name: true,
+        },
+      },
+      documentMeta: true,
+      team: {
+        select: {
+          teamEmail: true,
+          name: true,
+          url: true,
+        },
+      },
+    },
+  });
+
+  if (!envelope) {
+    throw new Error(`Envelope ${envelopeId} not found`);
+  }
+
+  const recipient = await prisma.recipient.findFirst({
+    where: {
+      id: recipientId,
+      envelopeId,
+    },
+  });
+
+  if (!recipient) {
+    throw new Error(`Recipient ${recipientId} not found on envelope ${envelopeId}`);
+  }
+
+  const { documentMeta, user: documentOwner } = envelope;
+
+  const isEmailEnabled = extractDerivedDocumentEmailSettings(documentMeta).ownerRecipientExpired;
+
+  if (!isEmailEnabled) {
+    return;
+  }
+
+  const { branding, emailLanguage, senderEmail } = await getEmailContext({
+    emailType: 'RECIPIENT',
+    source: {
+      type: 'team',
+      teamId: envelope.teamId,
+    },
+    meta: documentMeta,
+  });
+
+  const i18n = await getI18nInstance(emailLanguage);
+
+  const documentLink = `${NEXT_PUBLIC_WEBAPP_URL()}${formatDocumentsPath(envelope.team.url)}/${envelope.id}`;
+
+  const template = createElement(RecipientExpiredTemplate, {
+    documentName: envelope.title,
+    recipientName: recipient.name || recipient.email,
+    recipientEmail: recipient.email,
+    documentLink,
+    assetBaseUrl: NEXT_PUBLIC_WEBAPP_URL(),
+  });
+
+  await io.runTask('send-owner-recipient-expired-email', async () => {
+    const [html, text] = await Promise.all([
+      renderEmailWithI18N(template, { lang: emailLanguage, branding }),
+      renderEmailWithI18N(template, {
+        lang: emailLanguage,
+        branding,
+        plainText: true,
+      }),
+    ]);
+
+    await mailer.sendMail({
+      to: {
+        name: documentOwner.name || '',
+        address: documentOwner.email,
+      },
+      from: senderEmail,
+      subject: i18n._(
+        msg`Signing window expired for "${recipient.name || recipient.email}" on "${envelope.title}"`,
+      ),
+      html,
+      text,
+    });
+  });
+};
diff --git a/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.ts b/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.ts
new file mode 100644
index 000000000..1f312d8a3
--- /dev/null
+++ b/packages/lib/jobs/definitions/emails/send-owner-recipient-expired-email.ts
@@ -0,0 +1,32 @@
+import { z } from 'zod';
+
+import { type JobDefinition } from '../../client/_internal/job';
+
+const SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_ID = 'send.owner.recipient.expired.email';
+
+const SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_SCHEMA = z.object({
+  recipientId: z.number(),
+  envelopeId: z.string(),
+});
+
+export type TSendOwnerRecipientExpiredEmailJobDefinition = z.infer<
+  typeof SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_SCHEMA
+>;
+
+export const SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION = {
+  id: SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_ID,
+  name: 'Send Owner Recipient Expired Email',
+  version: '1.0.0',
+  trigger: {
+    name: SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_ID,
+    schema: SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_SCHEMA,
+  },
+  handler: async ({ payload, io }) => {
+    const handler = await import('./send-owner-recipient-expired-email.handler');
+
+    await handler.run({ payload, io });
+  },
+} as const satisfies JobDefinition<
+  typeof SEND_OWNER_RECIPIENT_EXPIRED_EMAIL_JOB_DEFINITION_ID,
+  TSendOwnerRecipientExpiredEmailJobDefinition
+>;
diff --git a/packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts b/packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts
new file mode 100644
index 000000000..2ca22a31c
--- /dev/null
+++ b/packages/lib/jobs/definitions/internal/expire-recipients-sweep.handler.ts
@@ -0,0 +1,53 @@
+import { DocumentStatus, SigningStatus } from '@prisma/client';
+
+import { prisma } from '@documenso/prisma';
+
+import { jobs } from '../../client';
+import type { JobRunIO } from '../../client/_internal/job';
+import type { TExpireRecipientsSweepJobDefinition } from './expire-recipients-sweep';
+
+export const run = async ({
+  io,
+}: {
+  payload: TExpireRecipientsSweepJobDefinition;
+  io: JobRunIO;
+}) => {
+  const now = new Date();
+
+  const expiredRecipients = await prisma.recipient.findMany({
+    where: {
+      expiresAt: {
+        lte: now,
+      },
+      expirationNotifiedAt: null,
+      signingStatus: {
+        notIn: [SigningStatus.SIGNED, SigningStatus.REJECTED],
+      },
+      envelope: {
+        status: DocumentStatus.PENDING,
+      },
+    },
+    select: {
+      id: true,
+    },
+    take: 1000, // Limit to 1000 to avoid long-running jobs. Will be picked up in the next run if there are more.
+  });
+
+  if (expiredRecipients.length === 0) {
+    io.logger.info('No expired recipients found');
+    return;
+  }
+
+  io.logger.info(`Found ${expiredRecipients.length} expired recipients`);
+
+  await Promise.allSettled(
+    expiredRecipients.map(async (recipient) => {
+      await jobs.triggerJob({
+        name: 'internal.process-recipient-expired',
+        payload: {
+          recipientId: recipient.id,
+        },
+      });
+    }),
+  );
+};
diff --git a/packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts b/packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts
new file mode 100644
index 000000000..c80de02b7
--- /dev/null
+++ b/packages/lib/jobs/definitions/internal/expire-recipients-sweep.ts
@@ -0,0 +1,30 @@
+import { z } from 'zod';
+
+import { type JobDefinition } from '../../client/_internal/job';
+
+const EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_ID = 'internal.expire-recipients-sweep';
+
+const EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_SCHEMA = z.object({});
+
+export type TExpireRecipientsSweepJobDefinition = z.infer<
+  typeof EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_SCHEMA
+>;
+
+export const EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION = {
+  id: EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_ID,
+  name: 'Expire Recipients Sweep',
+  version: '1.0.0',
+  trigger: {
+    name: EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_ID,
+    schema: EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_SCHEMA,
+    cron: '*/15 * * * *', // Every 15 minutes.
+  },
+  handler: async ({ payload, io }) => {
+    const handler = await import('./expire-recipients-sweep.handler');
+
+    await handler.run({ payload, io });
+  },
+} as const satisfies JobDefinition<
+  typeof EXPIRE_RECIPIENTS_SWEEP_JOB_DEFINITION_ID,
+  TExpireRecipientsSweepJobDefinition
+>;
diff --git a/packages/lib/jobs/definitions/internal/process-recipient-expired.handler.ts b/packages/lib/jobs/definitions/internal/process-recipient-expired.handler.ts
new file mode 100644
index 000000000..45e15edc5
--- /dev/null
+++ b/packages/lib/jobs/definitions/internal/process-recipient-expired.handler.ts
@@ -0,0 +1,95 @@
+import { SigningStatus, WebhookTriggerEvents } from '@prisma/client';
+
+import { prisma } from '@documenso/prisma';
+
+import { triggerWebhook } from '../../../server-only/webhooks/trigger/trigger-webhook';
+import { DOCUMENT_AUDIT_LOG_TYPE } from '../../../types/document-audit-logs';
+import {
+  ZWebhookDocumentSchema,
+  mapEnvelopeToWebhookDocumentPayload,
+} from '../../../types/webhook-payload';
+import { createDocumentAuditLogData } from '../../../utils/document-audit-logs';
+import { jobs } from '../../client';
+import type { JobRunIO } from '../../client/_internal/job';
+import type { TProcessRecipientExpiredJobDefinition } from './process-recipient-expired';
+
+export const run = async ({
+  payload,
+  io,
+}: {
+  payload: TProcessRecipientExpiredJobDefinition;
+  io: JobRunIO;
+}) => {
+  const { recipientId } = payload;
+
+  // Atomic idempotency guard — only one concurrent worker wins.
+  // Wrapping in runTask caches the result so that on retry the claim is not
+  // re-evaluated and subsequent steps can still proceed.
+  const claimedCount = await io.runTask('claim-recipient', async () => {
+    const result = await prisma.recipient.updateMany({
+      where: {
+        id: recipientId,
+        expirationNotifiedAt: null,
+        signingStatus: { notIn: [SigningStatus.SIGNED, SigningStatus.REJECTED] },
+      },
+      data: { expirationNotifiedAt: new Date() },
+    });
+
+    return result.count;
+  });
+
+  if (claimedCount === 0) {
+    io.logger.info(`Recipient ${recipientId} already processed or no longer eligible, skipping`);
+    return;
+  }
+
+  // Fetch recipient (now marked) with its envelope for downstream steps.
+  // Re-fetch after claiming so that expirationNotifiedAt reflects the updated value
+  // and webhook consumers see consistent state.
+  const recipient = await prisma.recipient.findUniqueOrThrow({
+    where: { id: recipientId },
+    include: {
+      envelope: {
+        include: { recipients: true, documentMeta: true },
+      },
+    },
+  });
+
+  const { envelope } = recipient;
+
+  io.logger.info(
+    `Recipient ${recipientId} (${recipient.email}) expired on envelope ${recipient.envelopeId}`,
+  );
+
+  // Create audit log entry — wrapped so a retry skips this if it already succeeded.
+  await io.runTask('create-audit-log', async () => {
+    await prisma.documentAuditLog.create({
+      data: createDocumentAuditLogData({
+        type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_RECIPIENT_EXPIRED,
+        envelopeId: recipient.envelopeId,
+        data: {
+          recipientEmail: recipient.email,
+          recipientName: recipient.name,
+          recipientId: recipient.id,
+        },
+      }),
+    });
+  });
+
+  // Trigger webhook for recipient expiration.
+  await triggerWebhook({
+    event: WebhookTriggerEvents.RECIPIENT_EXPIRED,
+    data: ZWebhookDocumentSchema.parse(mapEnvelopeToWebhookDocumentPayload(envelope)),
+    userId: envelope.userId,
+    teamId: envelope.teamId,
+  });
+
+  // Trigger email notification to the document owner.
+  await jobs.triggerJob({
+    name: 'send.owner.recipient.expired.email',
+    payload: {
+      recipientId: recipient.id,
+      envelopeId: recipient.envelopeId,
+    },
+  });
+};
diff --git a/packages/lib/jobs/definitions/internal/process-recipient-expired.ts b/packages/lib/jobs/definitions/internal/process-recipient-expired.ts
new file mode 100644
index 000000000..4945c9b80
--- /dev/null
+++ b/packages/lib/jobs/definitions/internal/process-recipient-expired.ts
@@ -0,0 +1,31 @@
+import { z } from 'zod';
+
+import { type JobDefinition } from '../../client/_internal/job';
+
+const PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_ID = 'internal.process-recipient-expired';
+
+const PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_SCHEMA = z.object({
+  recipientId: z.number(),
+});
+
+export type TProcessRecipientExpiredJobDefinition = z.infer<
+  typeof PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_SCHEMA
+>;
+
+export const PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION = {
+  id: PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_ID,
+  name: 'Process Recipient Expired',
+  version: '1.0.0',
+  trigger: {
+    name: PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_ID,
+    schema: PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_SCHEMA,
+  },
+  handler: async ({ payload, io }) => {
+    const handler = await import('./process-recipient-expired.handler');
+
+    await handler.run({ payload, io });
+  },
+} as const satisfies JobDefinition<
+  typeof PROCESS_RECIPIENT_EXPIRED_JOB_DEFINITION_ID,
+  TProcessRecipientExpiredJobDefinition
+>;
diff --git a/packages/lib/server-only/document/complete-document-with-token.ts b/packages/lib/server-only/document/complete-document-with-token.ts
index fe5126608..3b1ff67b8 100644
--- a/packages/lib/server-only/document/complete-document-with-token.ts
+++ b/packages/lib/server-only/document/complete-document-with-token.ts
@@ -29,6 +29,7 @@ import {
 import { extractDocumentAuthMethods } from '../../utils/document-auth';
 import type { EnvelopeIdOptions } from '../../utils/envelope';
 import { mapSecondaryIdToDocumentId, unsafeBuildEnvelopeIdQuery } from '../../utils/envelope';
+import { assertRecipientNotExpired } from '../../utils/recipients';
 import { getIsRecipientsTurnToSign } from '../recipient/get-is-recipient-turn';
 import { triggerWebhook } from '../webhooks/trigger/trigger-webhook';
 import { isRecipientAuthorized } from './is-recipient-authorized';
@@ -94,6 +95,8 @@ export const completeDocumentWithToken = async ({
 
   const [recipient] = envelope.recipients;
 
+  assertRecipientNotExpired(recipient);
+
   if (recipient.signingStatus === SigningStatus.SIGNED) {
     throw new Error(`Recipient ${recipient.id} has already signed`);
   }
diff --git a/packages/lib/server-only/document/reject-document-with-token.ts b/packages/lib/server-only/document/reject-document-with-token.ts
index 831feccf2..6e4cc2e46 100644
--- a/packages/lib/server-only/document/reject-document-with-token.ts
+++ b/packages/lib/server-only/document/reject-document-with-token.ts
@@ -1,4 +1,4 @@
-import { EnvelopeType, SigningStatus } from '@prisma/client';
+import { DocumentStatus, EnvelopeType, SigningStatus } from '@prisma/client';
 
 import { jobs } from '@documenso/lib/jobs/client';
 import { prisma } from '@documenso/prisma';
@@ -9,6 +9,7 @@ import type { RequestMetadata } from '../../universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '../../utils/document-audit-logs';
 import type { EnvelopeIdOptions } from '../../utils/envelope';
 import { mapSecondaryIdToDocumentId, unsafeBuildEnvelopeIdQuery } from '../../utils/envelope';
+import { assertRecipientNotExpired } from '../../utils/recipients';
 
 export type RejectDocumentWithTokenOptions = {
   token: string;
@@ -42,6 +43,14 @@ export async function rejectDocumentWithToken({
     });
   }
 
+  if (envelope.status !== DocumentStatus.PENDING) {
+    throw new AppError(AppErrorCode.INVALID_REQUEST, {
+      message: `Document ${envelope.id} must be pending to reject`,
+    });
+  }
+
+  assertRecipientNotExpired(recipient);
+
   // Update the recipient status to rejected
   const [updatedRecipient] = await prisma.$transaction([
     prisma.recipient.update({
diff --git a/packages/lib/server-only/document/resend-document.ts b/packages/lib/server-only/document/resend-document.ts
index f7995f041..632532830 100644
--- a/packages/lib/server-only/document/resend-document.ts
+++ b/packages/lib/server-only/document/resend-document.ts
@@ -11,6 +11,7 @@ import {
 
 import { mailer } from '@documenso/email/mailer';
 import { DocumentInviteEmailTemplate } from '@documenso/email/templates/document-invite';
+import { resolveExpiresAt } from '@documenso/lib/constants/envelope-expiration';
 import {
   RECIPIENT_ROLES_DESCRIPTION,
   RECIPIENT_ROLE_TO_EMAIL_TYPE,
@@ -94,11 +95,31 @@ export const resendDocument = async ({
     throw new Error('Can not send completed document');
   }
 
+  // Refresh the expiresAt on each resent recipient.
+  const expiresAt = resolveExpiresAt(envelope.documentMeta?.envelopeExpirationPeriod ?? null);
+
   const recipientsToRemind = envelope.recipients.filter(
     (recipient) =>
-      recipients.includes(recipient.id) && recipient.signingStatus === SigningStatus.NOT_SIGNED,
+      recipients.includes(recipient.id) &&
+      recipient.signingStatus === SigningStatus.NOT_SIGNED &&
+      recipient.role !== RecipientRole.CC,
   );
 
+  // Extend the expiration deadline for recipients being resent.
+  if (expiresAt && recipientsToRemind.length > 0) {
+    await prisma.recipient.updateMany({
+      where: {
+        id: {
+          in: recipientsToRemind.map((r) => r.id),
+        },
+      },
+      data: {
+        expiresAt,
+        expirationNotifiedAt: null,
+      },
+    });
+  }
+
   const isRecipientSigningRequestEmailEnabled = extractDerivedDocumentEmailSettings(
     envelope.documentMeta,
   ).recipientSigningRequest;
diff --git a/packages/lib/server-only/document/send-document.ts b/packages/lib/server-only/document/send-document.ts
index 4c6ae4493..0407b34d1 100644
--- a/packages/lib/server-only/document/send-document.ts
+++ b/packages/lib/server-only/document/send-document.ts
@@ -10,6 +10,7 @@ import {
   WebhookTriggerEvents,
 } from '@prisma/client';
 
+import { resolveExpiresAt } from '@documenso/lib/constants/envelope-expiration';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { ApiRequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '@documenso/lib/utils/document-audit-logs';
@@ -257,6 +258,28 @@ export const sendDocument = async ({
       });
     }
 
+    const expiresAt = resolveExpiresAt(envelope.documentMeta?.envelopeExpirationPeriod ?? null);
+
+    // Set expiresAt on each recipient that hasn't already signed/rejected.
+    // Exclude CC recipients since they don't sign and shouldn't be subject to expiry.
+    if (expiresAt) {
+      await tx.recipient.updateMany({
+        where: {
+          envelopeId: envelope.id,
+          signingStatus: {
+            notIn: [SigningStatus.SIGNED, SigningStatus.REJECTED],
+          },
+          role: {
+            not: RecipientRole.CC,
+          },
+        },
+        data: {
+          expiresAt,
+          expirationNotifiedAt: null,
+        },
+      });
+    }
+
     return await tx.envelope.update({
       where: {
         id: envelope.id,
diff --git a/packages/lib/server-only/envelope/get-envelope-for-direct-template-signing.ts b/packages/lib/server-only/envelope/get-envelope-for-direct-template-signing.ts
index 7957ef40f..d6be78773 100644
--- a/packages/lib/server-only/envelope/get-envelope-for-direct-template-signing.ts
+++ b/packages/lib/server-only/envelope/get-envelope-for-direct-template-signing.ts
@@ -163,6 +163,7 @@ export const getEnvelopeForDirectTemplateSigning = async ({
     isRecipientsTurn: true,
     isCompleted: false,
     isRejected: false,
+    isExpired: false,
     sender,
     settings: {
       includeSenderDetails: settings.includeSenderDetails,
diff --git a/packages/lib/server-only/envelope/get-envelope-for-recipient-signing.ts b/packages/lib/server-only/envelope/get-envelope-for-recipient-signing.ts
index a66051ad7..6141b33c2 100644
--- a/packages/lib/server-only/envelope/get-envelope-for-recipient-signing.ts
+++ b/packages/lib/server-only/envelope/get-envelope-for-recipient-signing.ts
@@ -13,6 +13,7 @@ import { AppError, AppErrorCode } from '../../errors/app-error';
 import type { TDocumentAuthMethods } from '../../types/document-auth';
 import { ZEnvelopeFieldSchema, ZFieldSchema } from '../../types/field';
 import { ZRecipientLiteSchema } from '../../types/recipient';
+import { isRecipientExpired } from '../../utils/recipients';
 import { isRecipientAuthorized } from '../document/is-recipient-authorized';
 import { getTeamSettings } from '../team/get-team-settings';
 
@@ -56,7 +57,9 @@ export const ZEnvelopeForSigningResponse = z.object({
       email: true,
       name: true,
       documentDeletedAt: true,
-      expired: true,
+      expired: true, //!: deprecated Not in use. To be removed in a future migration.
+      expiresAt: true,
+      expirationNotifiedAt: true,
       signedAt: true,
       authOptions: true,
       signingOrder: true,
@@ -102,7 +105,8 @@ export const ZEnvelopeForSigningResponse = z.object({
     email: true,
     name: true,
     documentDeletedAt: true,
-    expired: true,
+    expiresAt: true,
+    expirationNotifiedAt: true,
     signedAt: true,
     authOptions: true,
     token: true,
@@ -126,6 +130,7 @@ export const ZEnvelopeForSigningResponse = z.object({
 
   isCompleted: z.boolean(),
   isRejected: z.boolean(),
+  isExpired: z.boolean(),
   isRecipientsTurn: z.boolean(),
 
   sender: z.object({
@@ -291,6 +296,7 @@ export const getEnvelopeForRecipientSigning = async ({
     isRejected:
       recipient.signingStatus === SigningStatus.REJECTED ||
       envelope.status === DocumentStatus.REJECTED,
+    isExpired: isRecipientExpired(recipient),
     sender,
     settings: {
       includeSenderDetails: settings.includeSenderDetails,
diff --git a/packages/lib/server-only/field/remove-signed-field-with-token.ts b/packages/lib/server-only/field/remove-signed-field-with-token.ts
index 70be50629..0995ba4a9 100644
--- a/packages/lib/server-only/field/remove-signed-field-with-token.ts
+++ b/packages/lib/server-only/field/remove-signed-field-with-token.ts
@@ -3,6 +3,7 @@ import { DocumentStatus, RecipientRole, SigningStatus } from '@prisma/client';
 import { DOCUMENT_AUDIT_LOG_TYPE } from '@documenso/lib/types/document-audit-logs';
 import type { RequestMetadata } from '@documenso/lib/universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '@documenso/lib/utils/document-audit-logs';
+import { assertRecipientNotExpired } from '@documenso/lib/utils/recipients';
 import { prisma } from '@documenso/prisma';
 
 export type RemovedSignedFieldWithTokenOptions = {
@@ -56,6 +57,8 @@ export const removeSignedFieldWithToken = async ({
     throw new Error(`Document ${envelope.id} must be pending`);
   }
 
+  assertRecipientNotExpired(recipient);
+
   if (
     recipient?.signingStatus === SigningStatus.SIGNED ||
     field.recipient.signingStatus === SigningStatus.SIGNED
diff --git a/packages/lib/server-only/field/sign-field-with-token.ts b/packages/lib/server-only/field/sign-field-with-token.ts
index 8c6c81c2b..f36b02a84 100644
--- a/packages/lib/server-only/field/sign-field-with-token.ts
+++ b/packages/lib/server-only/field/sign-field-with-token.ts
@@ -25,6 +25,7 @@ import {
 } from '../../types/field-meta';
 import type { RequestMetadata } from '../../universal/extract-request-metadata';
 import { createDocumentAuditLogData } from '../../utils/document-audit-logs';
+import { assertRecipientNotExpired } from '../../utils/recipients';
 import { validateFieldAuth } from '../document/validate-field-auth';
 
 export type SignFieldWithTokenOptions = {
@@ -108,6 +109,8 @@ export const signFieldWithToken = async ({
     throw new Error(`Document ${envelope.id} must be pending for signing`);
   }
 
+  assertRecipientNotExpired(recipient);
+
   if (
     recipient.signingStatus === SigningStatus.SIGNED ||
     field.recipient.signingStatus === SigningStatus.SIGNED
diff --git a/packages/lib/server-only/template/create-document-from-template.ts b/packages/lib/server-only/template/create-document-from-template.ts
index bb9ba9db2..6d848303b 100644
--- a/packages/lib/server-only/template/create-document-from-template.ts
+++ b/packages/lib/server-only/template/create-document-from-template.ts
@@ -17,6 +17,7 @@ import { nanoid, prefixedId } from '@documenso/lib/universal/id';
 import { prisma } from '@documenso/prisma';
 
 import { DEFAULT_DOCUMENT_DATE_FORMAT } from '../../constants/date-formats';
+import type { TEnvelopeExpirationPeriod } from '../../constants/envelope-expiration';
 import type { SupportedLanguageCodes } from '../../constants/i18n';
 import { AppError, AppErrorCode } from '../../errors/app-error';
 import { ZDefaultRecipientsSchema } from '../../types/default-recipients';
@@ -119,6 +120,7 @@ export type CreateDocumentFromTemplateOptions = {
     typedSignatureEnabled?: boolean;
     uploadSignatureEnabled?: boolean;
     drawSignatureEnabled?: boolean;
+    envelopeExpirationPeriod?: TEnvelopeExpirationPeriod | null;
   };
 
   formValues?: TDocumentFormValues;
@@ -521,6 +523,8 @@ export const createDocumentFromTemplate = async ({
         override?.drawSignatureEnabled ?? template.documentMeta?.drawSignatureEnabled,
       allowDictateNextSigner:
         override?.allowDictateNextSigner ?? template.documentMeta?.allowDictateNextSigner,
+      envelopeExpirationPeriod:
+        override?.envelopeExpirationPeriod ?? template.documentMeta?.envelopeExpirationPeriod,
     }),
   });
 
diff --git a/packages/lib/server-only/webhooks/trigger/generate-sample-data.ts b/packages/lib/server-only/webhooks/trigger/generate-sample-data.ts
index 47e3e7c53..86b63a23f 100644
--- a/packages/lib/server-only/webhooks/trigger/generate-sample-data.ts
+++ b/packages/lib/server-only/webhooks/trigger/generate-sample-data.ts
@@ -61,7 +61,8 @@ export const generateSampleWebhookPayload = (
         name: 'John Doe',
         token: 'SIGNING_TOKEN',
         documentDeletedAt: null,
-        expired: null,
+        expiresAt: null,
+        expirationNotifiedAt: null,
         signedAt: null,
         authOptions: null,
         signingOrder: 1,
@@ -81,7 +82,8 @@ export const generateSampleWebhookPayload = (
         name: 'John Doe',
         token: 'SIGNING_TOKEN',
         documentDeletedAt: null,
-        expired: null,
+        expiresAt: null,
+        expirationNotifiedAt: null,
         signedAt: null,
         authOptions: null,
         signingOrder: 1,
@@ -120,7 +122,8 @@ export const generateSampleWebhookPayload = (
             role: RecipientRole.VIEWER,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: null,
             signingOrder: 1,
@@ -139,7 +142,8 @@ export const generateSampleWebhookPayload = (
             role: RecipientRole.SIGNER,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: null,
             rejectionReason: null,
@@ -168,7 +172,8 @@ export const generateSampleWebhookPayload = (
             readStatus: ReadStatus.OPENED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: null,
             signingOrder: 1,
@@ -185,7 +190,8 @@ export const generateSampleWebhookPayload = (
             readStatus: ReadStatus.OPENED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: null,
             signingOrder: 1,
@@ -222,7 +228,8 @@ export const generateSampleWebhookPayload = (
             signingStatus: SigningStatus.SIGNED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signingOrder: 1,
             rejectionReason: null,
           },
@@ -243,7 +250,8 @@ export const generateSampleWebhookPayload = (
             signingStatus: SigningStatus.SIGNED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signingOrder: 1,
             rejectionReason: null,
           },
@@ -270,7 +278,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer 2',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: now,
             authOptions: {
               accessAuth: null,
@@ -291,7 +300,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer 1',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: now,
             authOptions: {
               accessAuth: null,
@@ -314,7 +324,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer 2',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: now,
             authOptions: {
               accessAuth: null,
@@ -335,7 +346,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer 1',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: now,
             authOptions: {
               accessAuth: null,
@@ -374,7 +386,8 @@ export const generateSampleWebhookPayload = (
             signingStatus: SigningStatus.REJECTED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signingOrder: 1,
           },
         ],
@@ -391,7 +404,8 @@ export const generateSampleWebhookPayload = (
             signingStatus: SigningStatus.REJECTED,
             sendStatus: SendStatus.SENT,
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signingOrder: 1,
           },
         ],
@@ -425,6 +439,7 @@ export const generateSampleWebhookPayload = (
             recipientRemoved: true,
             documentCompleted: true,
             ownerDocumentCompleted: true,
+            ownerRecipientExpired: true,
             recipientSigningRequest: true,
           },
         },
@@ -437,7 +452,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer 1',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: {
               accessAuth: null,
@@ -460,7 +476,8 @@ export const generateSampleWebhookPayload = (
             name: 'Signer',
             token: 'SIGNING_TOKEN',
             documentDeletedAt: null,
-            expired: null,
+            expiresAt: null,
+            expirationNotifiedAt: null,
             signedAt: null,
             authOptions: {
               accessAuth: null,
@@ -480,5 +497,53 @@ export const generateSampleWebhookPayload = (
     };
   }
 
+  if (event === WebhookTriggerEvents.RECIPIENT_EXPIRED) {
+    const expiresAt = new Date(now.getTime() - 60 * 1000); // Expired 1 minute ago
+
+    return {
+      event,
+      payload: {
+        ...basePayload,
+        status: DocumentStatus.PENDING,
+        recipients: [
+          {
+            ...basePayload.recipients[0],
+            email: 'signer1@documenso.com',
+            name: 'Signer 1',
+            sendStatus: SendStatus.SENT,
+            documentDeletedAt: null,
+            expiresAt,
+            expirationNotifiedAt: now,
+            signedAt: null,
+            authOptions: null,
+            signingOrder: 1,
+            rejectionReason: null,
+            readStatus: ReadStatus.OPENED,
+            signingStatus: SigningStatus.NOT_SIGNED,
+          },
+        ],
+        Recipient: [
+          {
+            ...basePayload.Recipient[0],
+            email: 'signer1@documenso.com',
+            name: 'Signer 1',
+            sendStatus: SendStatus.SENT,
+            documentDeletedAt: null,
+            expiresAt,
+            expirationNotifiedAt: now,
+            signedAt: null,
+            authOptions: null,
+            signingOrder: 1,
+            rejectionReason: null,
+            readStatus: ReadStatus.OPENED,
+            signingStatus: SigningStatus.NOT_SIGNED,
+          },
+        ],
+      },
+      createdAt: now.toISOString(),
+      webhookEndpoint: webhookUrl,
+    };
+  }
+
   throw new Error(`Unsupported event type: ${event}`);
 };
diff --git a/packages/lib/server-only/webhooks/zapier/list-documents.ts b/packages/lib/server-only/webhooks/zapier/list-documents.ts
index 9aed6a878..105d4cd83 100644
--- a/packages/lib/server-only/webhooks/zapier/list-documents.ts
+++ b/packages/lib/server-only/webhooks/zapier/list-documents.ts
@@ -67,7 +67,9 @@ export const listDocumentsHandler = async (req: Request) => {
           name: recipient.name,
           token: recipient.token,
           documentDeletedAt: recipient.documentDeletedAt,
-          expired: recipient.expired,
+          expired: recipient.expired, // !: deprecated Not in use. To be removed in a future migration.
+          expiresAt: recipient.expiresAt,
+          expirationNotifiedAt: recipient.expirationNotifiedAt,
           signedAt: recipient.signedAt,
           authOptions: recipient.authOptions,
           signingOrder: recipient.signingOrder,
diff --git a/packages/lib/types/document-audit-logs.ts b/packages/lib/types/document-audit-logs.ts
index f4d0508da..3eb518d5c 100644
--- a/packages/lib/types/document-audit-logs.ts
+++ b/packages/lib/types/document-audit-logs.ts
@@ -40,6 +40,7 @@ export const ZDocumentAuditLogTypeSchema = z.enum([
   'DOCUMENT_VIEWED', // When the document is viewed by a recipient.
   'DOCUMENT_RECIPIENT_REJECTED', // When a recipient rejects the document.
   'DOCUMENT_RECIPIENT_COMPLETED', // When a recipient completes all their required tasks for the document.
+  'DOCUMENT_RECIPIENT_EXPIRED', // When a recipient's signing window expires.
   'DOCUMENT_SENT', // When the document transitions from DRAFT to PENDING.
   'DOCUMENT_TITLE_UPDATED', // When the document title is updated.
   'DOCUMENT_EXTERNAL_ID_UPDATED', // When the document external ID is updated.
@@ -694,6 +695,18 @@ export const ZDocumentAuditLogEventDocumentDelegatedOwnerCreatedSchema = z.objec
   }),
 });
 
+/**
+ * Event: Recipient's signing window expired.
+ */
+export const ZDocumentAuditLogEventRecipientExpiredSchema = z.object({
+  type: z.literal(DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_RECIPIENT_EXPIRED),
+  data: z.object({
+    recipientEmail: z.string(),
+    recipientName: z.string(),
+    recipientId: z.number(),
+  }),
+});
+
 export const ZDocumentAuditLogBaseSchema = z.object({
   id: z.string(),
   createdAt: z.date(),
@@ -739,6 +752,7 @@ export const ZDocumentAuditLogSchema = ZDocumentAuditLogBaseSchema.and(
     ZDocumentAuditLogEventRecipientAddedSchema,
     ZDocumentAuditLogEventRecipientUpdatedSchema,
     ZDocumentAuditLogEventRecipientRemovedSchema,
+    ZDocumentAuditLogEventRecipientExpiredSchema,
   ]),
 );
 
diff --git a/packages/lib/types/document-email.ts b/packages/lib/types/document-email.ts
index 0d2d2b52e..cc659519b 100644
--- a/packages/lib/types/document-email.ts
+++ b/packages/lib/types/document-email.ts
@@ -10,6 +10,7 @@ export enum DocumentEmailEvents {
   DocumentCompleted = 'documentCompleted',
   DocumentDeleted = 'documentDeleted',
   OwnerDocumentCompleted = 'ownerDocumentCompleted',
+  OwnerRecipientExpired = 'ownerRecipientExpired',
 }
 
 export const ZDocumentEmailSettingsSchema = z
@@ -52,6 +53,12 @@ export const ZDocumentEmailSettingsSchema = z
       .boolean()
       .describe('Whether to send an email to the document owner when the document is complete.')
       .default(true),
+    ownerRecipientExpired: z
+      .boolean()
+      .describe(
+        "Whether to send an email to the document owner when a recipient's signing window has expired.",
+      )
+      .default(true),
   })
   .strip()
   .catch(() => ({ ...DEFAULT_DOCUMENT_EMAIL_SETTINGS }));
@@ -78,6 +85,7 @@ export const extractDerivedDocumentEmailSettings = (
     documentCompleted: false,
     documentDeleted: false,
     ownerDocumentCompleted: emailSettings.ownerDocumentCompleted,
+    ownerRecipientExpired: emailSettings.ownerRecipientExpired,
   };
 };
 
@@ -89,4 +97,5 @@ export const DEFAULT_DOCUMENT_EMAIL_SETTINGS: TDocumentEmailSettings = {
   documentCompleted: true,
   documentDeleted: true,
   ownerDocumentCompleted: true,
+  ownerRecipientExpired: true,
 };
diff --git a/packages/lib/types/document-meta.ts b/packages/lib/types/document-meta.ts
index bb19f12aa..82a4af99c 100644
--- a/packages/lib/types/document-meta.ts
+++ b/packages/lib/types/document-meta.ts
@@ -3,6 +3,7 @@ import { DocumentDistributionMethod, DocumentSigningOrder } from '@prisma/client
 import { z } from 'zod';
 
 import { VALID_DATE_FORMAT_VALUES } from '@documenso/lib/constants/date-formats';
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { isValidRedirectUrl } from '@documenso/lib/utils/is-valid-redirect-url';
 import { DocumentMetaSchema } from '@documenso/prisma/generated/zod/modelSchema/DocumentMetaSchema';
@@ -128,6 +129,7 @@ export const ZDocumentMetaCreateSchema = z.object({
   emailId: z.string().nullish(),
   emailReplyTo: z.string().email().nullish(),
   emailSettings: ZDocumentEmailSettingsSchema.nullish(),
+  envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
 });
 
 export type TDocumentMetaCreate = z.infer<typeof ZDocumentMetaCreateSchema>;
diff --git a/packages/lib/types/document.ts b/packages/lib/types/document.ts
index 140e453cb..92daff749 100644
--- a/packages/lib/types/document.ts
+++ b/packages/lib/types/document.ts
@@ -71,6 +71,7 @@ export const ZDocumentSchema = LegacyDocumentSchema.pick({
     emailSettings: true,
     emailId: true,
     emailReplyTo: true,
+    envelopeExpirationPeriod: true,
   }).extend({
     password: z.string().nullable().default(null),
     documentId: z.number().default(-1).optional(),
diff --git a/packages/lib/types/envelope.ts b/packages/lib/types/envelope.ts
index 7c83afcdf..f3ea46f15 100644
--- a/packages/lib/types/envelope.ts
+++ b/packages/lib/types/envelope.ts
@@ -55,6 +55,7 @@ export const ZEnvelopeSchema = EnvelopeSchema.pick({
     emailSettings: true,
     emailId: true,
     emailReplyTo: true,
+    envelopeExpirationPeriod: true,
   }),
   recipients: ZEnvelopeRecipientLiteSchema.array(),
   fields: ZEnvelopeFieldSchema.array(),
diff --git a/packages/lib/types/recipient.ts b/packages/lib/types/recipient.ts
index cea2cd8b6..f8919cd3f 100644
--- a/packages/lib/types/recipient.ts
+++ b/packages/lib/types/recipient.ts
@@ -23,7 +23,9 @@ export const ZRecipientSchema = RecipientSchema.pick({
   name: true,
   token: true,
   documentDeletedAt: true,
-  expired: true,
+  expired: true, // deprecated Not in use. To be removed in a future migration.
+  expiresAt: true,
+  expirationNotifiedAt: true,
   signedAt: true,
   authOptions: true,
   signingOrder: true,
@@ -50,7 +52,9 @@ export const ZRecipientLiteSchema = RecipientSchema.pick({
   name: true,
   token: true,
   documentDeletedAt: true,
-  expired: true,
+  expired: true, // !: deprecated Not in use. To be removed in a future migration.
+  expiresAt: true,
+  expirationNotifiedAt: true,
   signedAt: true,
   authOptions: true,
   signingOrder: true,
@@ -75,7 +79,9 @@ export const ZRecipientManySchema = RecipientSchema.pick({
   name: true,
   token: true,
   documentDeletedAt: true,
-  expired: true,
+  expired: true, // !: deprecated Not in use. To be removed in a future migration.
+  expiresAt: true,
+  expirationNotifiedAt: true,
   signedAt: true,
   authOptions: true,
   signingOrder: true,
diff --git a/packages/lib/types/webhook-payload.ts b/packages/lib/types/webhook-payload.ts
index 31343656e..398a5e444 100644
--- a/packages/lib/types/webhook-payload.ts
+++ b/packages/lib/types/webhook-payload.ts
@@ -26,7 +26,8 @@ export const ZWebhookRecipientSchema = z.object({
   name: z.string(),
   token: z.string(),
   documentDeletedAt: z.date().nullable(),
-  expired: z.date().nullable(),
+  expiresAt: z.date().nullable(),
+  expirationNotifiedAt: z.date().nullable(),
   signedAt: z.date().nullable(),
   authOptions: z.any().nullable(),
   signingOrder: z.number().nullable(),
@@ -116,7 +117,8 @@ export const mapEnvelopeToWebhookDocumentPayload = (
     name: recipient.name,
     token: recipient.token,
     documentDeletedAt: recipient.documentDeletedAt,
-    expired: recipient.expired,
+    expiresAt: recipient.expiresAt,
+    expirationNotifiedAt: recipient.expirationNotifiedAt,
     signedAt: recipient.signedAt,
     authOptions: recipient.authOptions,
     signingOrder: recipient.signingOrder,
diff --git a/packages/lib/utils/document-audit-logs.ts b/packages/lib/utils/document-audit-logs.ts
index a769680d8..5067752cf 100644
--- a/packages/lib/utils/document-audit-logs.ts
+++ b/packages/lib/utils/document-audit-logs.ts
@@ -571,6 +571,14 @@ export const formatDocumentAuditLogAction = (
       you: msg`You deleted an envelope item with title ${data.envelopeItemTitle}`,
       user: msg`${user} deleted an envelope item with title ${data.envelopeItemTitle}`,
     }))
+    .with({ type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_RECIPIENT_EXPIRED }, ({ data }) => ({
+      anonymous: msg({
+        message: `Recipient signing window expired`,
+        context: `Audit log format`,
+      }),
+      you: msg`Signing window expired for ${data.recipientName || data.recipientEmail}`,
+      user: msg`Signing window expired for ${data.recipientName || data.recipientEmail}`,
+    }))
     .with({ type: DOCUMENT_AUDIT_LOG_TYPE.DOCUMENT_DELEGATED_OWNER_CREATED }, ({ data }) => {
       const message = msg({
         message: `The document ownership was delegated to ${data.delegatedOwnerName || data.delegatedOwnerEmail} on behalf of ${data.teamName}`,
diff --git a/packages/lib/utils/document.ts b/packages/lib/utils/document.ts
index 45f2d9f26..58753a6c8 100644
--- a/packages/lib/utils/document.ts
+++ b/packages/lib/utils/document.ts
@@ -62,6 +62,10 @@ export const extractDerivedDocumentMeta = (
     emailReplyTo: meta.emailReplyTo ?? settings.emailReplyTo,
     emailSettings:
       meta.emailSettings || settings.emailDocumentSettings || DEFAULT_DOCUMENT_EMAIL_SETTINGS,
+
+    // Envelope expiration.
+    envelopeExpirationPeriod:
+      meta.envelopeExpirationPeriod ?? settings.envelopeExpirationPeriod ?? null,
   } satisfies Omit<DocumentMeta, 'id'>;
 };
 
diff --git a/packages/lib/utils/organisations.ts b/packages/lib/utils/organisations.ts
index a75feb18b..b38e9a697 100644
--- a/packages/lib/utils/organisations.ts
+++ b/packages/lib/utils/organisations.ts
@@ -8,6 +8,7 @@ import {
 import type { ORGANISATION_MEMBER_ROLE_MAP } from '@documenso/lib/constants/organisations-translations';
 
 import { DEFAULT_DOCUMENT_DATE_FORMAT } from '../constants/date-formats';
+import { DEFAULT_ENVELOPE_EXPIRATION_PERIOD } from '../constants/envelope-expiration';
 import {
   LOWEST_ORGANISATION_ROLE,
   ORGANISATION_MEMBER_ROLE_HIERARCHY,
@@ -138,6 +139,9 @@ export const generateDefaultOrganisationSettings = (): Omit<
     emailDocumentSettings: DEFAULT_DOCUMENT_EMAIL_SETTINGS,
 
     defaultRecipients: null,
+
+    envelopeExpirationPeriod: DEFAULT_ENVELOPE_EXPIRATION_PERIOD,
+
     aiFeaturesEnabled: false,
   };
 };
diff --git a/packages/lib/utils/recipients.ts b/packages/lib/utils/recipients.ts
index aa3021324..3ee2e7119 100644
--- a/packages/lib/utils/recipients.ts
+++ b/packages/lib/utils/recipients.ts
@@ -5,6 +5,7 @@ import { z } from 'zod';
 import { isSignatureFieldType } from '@documenso/prisma/guards/is-signature-field';
 
 import { NEXT_PUBLIC_WEBAPP_URL } from '../constants/app';
+import { AppError, AppErrorCode } from '../errors/app-error';
 import { extractLegacyIds } from '../universal/id';
 
 /**
@@ -94,3 +95,23 @@ export const mapRecipientToLegacyRecipient = (
 export const isRecipientEmailValidForSending = (recipient: Pick<Recipient, 'email'>) => {
   return z.string().email().safeParse(recipient.email).success;
 };
+
+/**
+ * Whether the recipient's signing window has expired.
+ */
+export const isRecipientExpired = (recipient: { expiresAt: Date | null }) => {
+  return Boolean(recipient.expiresAt && new Date(recipient.expiresAt) <= new Date());
+};
+
+/**
+ * Asserts that the recipient's signing window has not expired.
+ *
+ * Throws an AppError with RECIPIENT_EXPIRED if the expiration date has passed.
+ */
+export const assertRecipientNotExpired = (recipient: { expiresAt: Date | null }) => {
+  if (isRecipientExpired(recipient)) {
+    throw new AppError(AppErrorCode.RECIPIENT_EXPIRED, {
+      message: 'Recipient signing window has expired',
+    });
+  }
+};
diff --git a/packages/lib/utils/teams.ts b/packages/lib/utils/teams.ts
index d1274b613..02fc562c1 100644
--- a/packages/lib/utils/teams.ts
+++ b/packages/lib/utils/teams.ts
@@ -205,6 +205,9 @@ export const generateDefaultTeamSettings = (): Omit<TeamGlobalSettings, 'id' | '
     // emailReplyToName: null,
 
     defaultRecipients: null,
+
+    envelopeExpirationPeriod: null,
+
     aiFeaturesEnabled: null,
   };
 };
diff --git a/packages/prisma/migrations/20260219091107_add_recipient_expirations/migration.sql b/packages/prisma/migrations/20260219091107_add_recipient_expirations/migration.sql
new file mode 100644
index 000000000..9b052674c
--- /dev/null
+++ b/packages/prisma/migrations/20260219091107_add_recipient_expirations/migration.sql
@@ -0,0 +1,18 @@
+-- AlterEnum
+ALTER TYPE "WebhookTriggerEvents" ADD VALUE 'RECIPIENT_EXPIRED';
+
+-- AlterTable
+ALTER TABLE "DocumentMeta" ADD COLUMN     "envelopeExpirationPeriod" JSONB;
+
+-- AlterTable
+ALTER TABLE "OrganisationGlobalSettings" ADD COLUMN     "envelopeExpirationPeriod" JSONB;
+
+-- AlterTable
+ALTER TABLE "Recipient" ADD COLUMN     "expirationNotifiedAt" TIMESTAMP(3),
+ADD COLUMN     "expiresAt" TIMESTAMP(3);
+
+-- AlterTable
+ALTER TABLE "TeamGlobalSettings" ADD COLUMN     "envelopeExpirationPeriod" JSONB;
+
+-- CreateIndex
+CREATE INDEX "Recipient_expiresAt_idx" ON "Recipient"("expiresAt");
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 886c6ea9c..17cbb166c 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -172,6 +172,7 @@ enum WebhookTriggerEvents {
   DOCUMENT_COMPLETED
   DOCUMENT_REJECTED
   DOCUMENT_CANCELLED
+  RECIPIENT_EXPIRED
 }
 
 model Webhook {
@@ -500,7 +501,7 @@ enum DocumentDistributionMethod {
   NONE
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
 model DocumentMeta {
   id                     String               @id @default(cuid())
   subject                String?
@@ -522,6 +523,8 @@ model DocumentMeta {
   emailReplyTo  String?
   emailId       String?
 
+  envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
+
   envelope Envelope?
 }
 
@@ -569,29 +572,32 @@ enum RecipientRole {
 
 /// @zod.import(["import { ZRecipientAuthOptionsSchema } from '@documenso/lib/types/document-auth';"])
 model Recipient {
-  id                Int           @id @default(autoincrement())
-  envelopeId        String
-  email             String        @db.VarChar(255)
-  name              String        @default("") @db.VarChar(255)
-  token             String
-  documentDeletedAt DateTime?
-  expired           DateTime?
-  signedAt          DateTime?
-  authOptions       Json? /// [RecipientAuthOptions] @zod.custom.use(ZRecipientAuthOptionsSchema)
-  signingOrder      Int? /// @zod.number.describe("The order in which the recipient should sign the document. Only works if the document is set to sequential signing.")
-  rejectionReason   String?
-  role              RecipientRole @default(SIGNER)
-  readStatus        ReadStatus    @default(NOT_OPENED)
-  signingStatus     SigningStatus @default(NOT_SIGNED)
-  sendStatus        SendStatus    @default(NOT_SENT)
-  envelope          Envelope      @relation(fields: [envelopeId], references: [id], onDelete: Cascade)
-  fields            Field[]
-  signatures        Signature[]
+  id                   Int           @id @default(autoincrement())
+  envelopeId           String
+  email                String        @db.VarChar(255)
+  name                 String        @default("") @db.VarChar(255)
+  token                String
+  documentDeletedAt    DateTime?
+  expired              DateTime? // deprecated Not in use. To be removed in a future migration.
+  expiresAt            DateTime?
+  expirationNotifiedAt DateTime?
+  signedAt             DateTime?
+  authOptions          Json? /// [RecipientAuthOptions] @zod.custom.use(ZRecipientAuthOptionsSchema)
+  signingOrder         Int? /// @zod.number.describe("The order in which the recipient should sign the document. Only works if the document is set to sequential signing.")
+  rejectionReason      String?
+  role                 RecipientRole @default(SIGNER)
+  readStatus           ReadStatus    @default(NOT_OPENED)
+  signingStatus        SigningStatus @default(NOT_SIGNED)
+  sendStatus           SendStatus    @default(NOT_SENT)
+  envelope             Envelope      @relation(fields: [envelopeId], references: [id], onDelete: Cascade)
+  fields               Field[]
+  signatures           Signature[]
 
   @@index([token])
   @@index([email])
   @@index([envelopeId])
   @@index([signedAt])
+  @@index([expiresAt])
 }
 
 enum FieldType {
@@ -808,7 +814,7 @@ enum OrganisationMemberInviteStatus {
   DECLINED
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
 model OrganisationGlobalSettings {
   id           String        @id
   organisation Organisation?
@@ -840,11 +846,13 @@ model OrganisationGlobalSettings {
   brandingUrl            String  @default("")
   brandingCompanyDetails String  @default("")
 
+  envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
+
   // AI features settings.
   aiFeaturesEnabled Boolean @default(false)
 }
 
-/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';"])
+/// @zod.import(["import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';", "import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';", "import { ZEnvelopeExpirationPeriod as ZEnvelopeExpirationPeriodSchema } from '@documenso/lib/constants/envelope-expiration';"])
 model TeamGlobalSettings {
   id   String @id
   team Team?
@@ -877,6 +885,8 @@ model TeamGlobalSettings {
   brandingUrl            String?
   brandingCompanyDetails String?
 
+  envelopeExpirationPeriod Json? /// [EnvelopeExpirationPeriod] @zod.custom.use(ZEnvelopeExpirationPeriodSchema)
+
   // AI features settings.
   aiFeaturesEnabled Boolean?
 }
diff --git a/packages/trpc/server/envelope-router/use-envelope.types.ts b/packages/trpc/server/envelope-router/use-envelope.types.ts
index 5121ba31a..84b334763 100644
--- a/packages/trpc/server/envelope-router/use-envelope.types.ts
+++ b/packages/trpc/server/envelope-router/use-envelope.types.ts
@@ -1,6 +1,7 @@
 import { z } from 'zod';
 import { zfd } from 'zod-form-data';
 
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
 import { ZDocumentFormValuesSchema } from '@documenso/lib/types/document-form-values';
 import {
@@ -97,6 +98,7 @@ export const ZUseEnvelopePayloadSchema = z.object({
       uploadSignatureEnabled: ZDocumentMetaUploadSignatureEnabledSchema.optional(),
       drawSignatureEnabled: ZDocumentMetaDrawSignatureEnabledSchema.optional(),
       allowDictateNextSigner: z.boolean().optional(),
+      envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
     })
     .describe('Override values from the template for the created document.')
     .optional(),
diff --git a/packages/trpc/server/organisation-router/update-organisation-settings.ts b/packages/trpc/server/organisation-router/update-organisation-settings.ts
index cd512e8c0..7dfa9b033 100644
--- a/packages/trpc/server/organisation-router/update-organisation-settings.ts
+++ b/packages/trpc/server/organisation-router/update-organisation-settings.ts
@@ -38,6 +38,7 @@ export const updateOrganisationSettingsRoute = authenticatedProcedure
       drawSignatureEnabled,
       defaultRecipients,
       delegateDocumentOwnership,
+      envelopeExpirationPeriod,
 
       // Branding related settings.
       brandingEnabled,
@@ -148,6 +149,8 @@ export const updateOrganisationSettingsRoute = authenticatedProcedure
             drawSignatureEnabled,
             defaultRecipients: defaultRecipients === null ? Prisma.DbNull : defaultRecipients,
             delegateDocumentOwnership: derivedDelegateDocumentOwnership,
+            envelopeExpirationPeriod:
+              envelopeExpirationPeriod === null ? Prisma.DbNull : envelopeExpirationPeriod,
 
             // Branding related settings.
             brandingEnabled,
diff --git a/packages/trpc/server/organisation-router/update-organisation-settings.types.ts b/packages/trpc/server/organisation-router/update-organisation-settings.types.ts
index 86a8ccb6f..1a294c078 100644
--- a/packages/trpc/server/organisation-router/update-organisation-settings.types.ts
+++ b/packages/trpc/server/organisation-router/update-organisation-settings.types.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
@@ -25,6 +26,7 @@ export const ZUpdateOrganisationSettingsRequestSchema = z.object({
     drawSignatureEnabled: z.boolean().optional(),
     defaultRecipients: ZDefaultRecipientsSchema.nullish(),
     delegateDocumentOwnership: z.boolean().nullish(),
+    envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.optional(),
 
     // Branding related settings.
     brandingEnabled: z.boolean().optional(),
diff --git a/packages/trpc/server/team-router/update-team-settings.ts b/packages/trpc/server/team-router/update-team-settings.ts
index 4e3f0eef0..f764bc95d 100644
--- a/packages/trpc/server/team-router/update-team-settings.ts
+++ b/packages/trpc/server/team-router/update-team-settings.ts
@@ -40,6 +40,7 @@ export const updateTeamSettingsRoute = authenticatedProcedure
       uploadSignatureEnabled,
       drawSignatureEnabled,
       delegateDocumentOwnership,
+      envelopeExpirationPeriod,
 
       // Branding related settings.
       brandingEnabled,
@@ -154,6 +155,8 @@ export const updateTeamSettingsRoute = authenticatedProcedure
             uploadSignatureEnabled,
             drawSignatureEnabled,
             delegateDocumentOwnership,
+            envelopeExpirationPeriod:
+              envelopeExpirationPeriod === null ? Prisma.DbNull : envelopeExpirationPeriod,
 
             // Branding related settings.
             brandingEnabled,
diff --git a/packages/trpc/server/team-router/update-team-settings.types.ts b/packages/trpc/server/team-router/update-team-settings.types.ts
index c0b9a26b5..f9ab1f097 100644
--- a/packages/trpc/server/team-router/update-team-settings.types.ts
+++ b/packages/trpc/server/team-router/update-team-settings.types.ts
@@ -1,5 +1,6 @@
 import { z } from 'zod';
 
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import { SUPPORTED_LANGUAGE_CODES } from '@documenso/lib/constants/i18n';
 import { ZDefaultRecipientsSchema } from '@documenso/lib/types/default-recipients';
 import { ZDocumentEmailSettingsSchema } from '@documenso/lib/types/document-email';
@@ -28,6 +29,7 @@ export const ZUpdateTeamSettingsRequestSchema = z.object({
     uploadSignatureEnabled: z.boolean().nullish(),
     drawSignatureEnabled: z.boolean().nullish(),
     delegateDocumentOwnership: z.boolean().nullish(),
+    envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
 
     // Branding related settings.
     brandingEnabled: z.boolean().nullish(),
diff --git a/packages/trpc/server/template-router/schema.ts b/packages/trpc/server/template-router/schema.ts
index 5b02d5cc4..1bc9f0e39 100644
--- a/packages/trpc/server/template-router/schema.ts
+++ b/packages/trpc/server/template-router/schema.ts
@@ -2,6 +2,7 @@ import { DocumentSigningOrder, DocumentVisibility, TemplateType } from '@prisma/
 import { z } from 'zod';
 import { zfd } from 'zod-form-data';
 
+import { ZEnvelopeExpirationPeriod } from '@documenso/lib/constants/envelope-expiration';
 import { ZDocumentSchema } from '@documenso/lib/types/document';
 import {
   ZDocumentAccessAuthTypesSchema,
@@ -160,6 +161,7 @@ export const ZCreateDocumentFromTemplateRequestSchema = z.object({
       uploadSignatureEnabled: ZDocumentMetaUploadSignatureEnabledSchema.optional(),
       drawSignatureEnabled: ZDocumentMetaDrawSignatureEnabledSchema.optional(),
       allowDictateNextSigner: z.boolean().optional(),
+      envelopeExpirationPeriod: ZEnvelopeExpirationPeriod.nullish(),
     })
     .describe('Override values from the template for the created document.')
     .optional(),
diff --git a/packages/ui/components/document/document-email-checkboxes.tsx b/packages/ui/components/document/document-email-checkboxes.tsx
index a1c35c828..dc846abbd 100644
--- a/packages/ui/components/document/document-email-checkboxes.tsx
+++ b/packages/ui/components/document/document-email-checkboxes.tsx
@@ -34,7 +34,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.RecipientSigned}
         >
           <Trans>Email the owner when a recipient signs</Trans>
@@ -44,7 +44,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Recipient signed email</Trans>
@@ -72,7 +72,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.RecipientSigningRequest}
         >
           <Trans>Email recipients with a signing request</Trans>
@@ -82,7 +82,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Recipient signing request email</Trans>
@@ -110,7 +110,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.RecipientRemoved}
         >
           <Trans>Email recipients when they're removed from a pending document</Trans>
@@ -120,7 +120,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Recipient removed email</Trans>
@@ -148,7 +148,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.DocumentPending}
         >
           <Trans>Email the signer if the document is still pending</Trans>
@@ -158,7 +158,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Document pending email</Trans>
@@ -187,7 +187,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.DocumentCompleted}
         >
           <Trans>Email recipients when the document is completed</Trans>
@@ -197,7 +197,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Document completed email</Trans>
@@ -225,7 +225,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.DocumentDeleted}
         >
           <Trans>Email recipients when a pending document is deleted</Trans>
@@ -235,7 +235,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Document deleted email</Trans>
@@ -263,7 +263,7 @@ export const DocumentEmailCheckboxes = ({
         />
 
         <label
-          className="text-muted-foreground ml-2 flex flex-row items-center text-sm"
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
           htmlFor={DocumentEmailEvents.OwnerDocumentCompleted}
         >
           <Trans>Email the owner when the document is completed</Trans>
@@ -273,7 +273,7 @@ export const DocumentEmailCheckboxes = ({
               <InfoIcon className="mx-2 h-4 w-4" />
             </TooltipTrigger>
 
-            <TooltipContent className="text-foreground max-w-md space-y-2 p-4">
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
               <h2>
                 <strong>
                   <Trans>Document completed email</Trans>
@@ -290,6 +290,45 @@ export const DocumentEmailCheckboxes = ({
           </Tooltip>
         </label>
       </div>
+
+      <div className="flex flex-row items-center">
+        <Checkbox
+          id={DocumentEmailEvents.OwnerRecipientExpired}
+          className="h-5 w-5"
+          checked={value.ownerRecipientExpired}
+          onCheckedChange={(checked) =>
+            onChange({ ...value, [DocumentEmailEvents.OwnerRecipientExpired]: Boolean(checked) })
+          }
+        />
+
+        <label
+          className="ml-2 flex flex-row items-center text-sm text-muted-foreground"
+          htmlFor={DocumentEmailEvents.OwnerRecipientExpired}
+        >
+          <Trans>Send recipient expired email to the owner</Trans>
+
+          <Tooltip>
+            <TooltipTrigger>
+              <InfoIcon className="mx-2 h-4 w-4" />
+            </TooltipTrigger>
+
+            <TooltipContent className="max-w-md space-y-2 p-4 text-foreground">
+              <h2>
+                <strong>
+                  <Trans>Recipient expired email</Trans>
+                </strong>
+              </h2>
+
+              <p>
+                <Trans>
+                  This will be sent to the document owner when a recipient's signing window has
+                  expired.
+                </Trans>
+              </p>
+            </TooltipContent>
+          </Tooltip>
+        </label>
+      </div>
     </div>
   );
 };
diff --git a/packages/ui/components/document/expiration-period-picker.tsx b/packages/ui/components/document/expiration-period-picker.tsx
new file mode 100644
index 000000000..f9e3094b9
--- /dev/null
+++ b/packages/ui/components/document/expiration-period-picker.tsx
@@ -0,0 +1,153 @@
+import type { MessageDescriptor } from '@lingui/core';
+import { msg } from '@lingui/core/macro';
+import { useLingui } from '@lingui/react';
+import { Trans } from '@lingui/react/macro';
+
+import type {
+  TEnvelopeExpirationDurationPeriod,
+  TEnvelopeExpirationPeriod,
+} from '@documenso/lib/constants/envelope-expiration';
+import { Input } from '@documenso/ui/primitives/input';
+import {
+  Select,
+  SelectContent,
+  SelectItem,
+  SelectTrigger,
+  SelectValue,
+} from '@documenso/ui/primitives/select';
+
+const EXPIRATION_UNITS: Array<{
+  value: TEnvelopeExpirationDurationPeriod['unit'];
+  label: MessageDescriptor;
+}> = [
+  { value: 'day', label: msg`Days` },
+  { value: 'week', label: msg`Weeks` },
+  { value: 'month', label: msg`Months` },
+  { value: 'year', label: msg`Years` },
+];
+
+type ExpirationMode = 'duration' | 'disabled' | 'inherit';
+
+const getMode = (value: TEnvelopeExpirationPeriod | null | undefined): ExpirationMode => {
+  if (!value) {
+    return 'inherit';
+  }
+
+  if ('disabled' in value) {
+    return 'disabled';
+  }
+
+  return 'duration';
+};
+
+const getAmount = (value: TEnvelopeExpirationPeriod | null | undefined): number => {
+  if (value && 'amount' in value) {
+    return value.amount;
+  }
+
+  return 1;
+};
+
+const getUnit = (
+  value: TEnvelopeExpirationPeriod | null | undefined,
+): TEnvelopeExpirationDurationPeriod['unit'] => {
+  if (value && 'unit' in value) {
+    return value.unit;
+  }
+
+  return 'month';
+};
+
+export type ExpirationPeriodPickerProps = {
+  value: TEnvelopeExpirationPeriod | null | undefined;
+  onChange: (value: TEnvelopeExpirationPeriod | null) => void;
+  disabled?: boolean;
+  inheritLabel?: string;
+};
+
+export const ExpirationPeriodPicker = ({
+  value,
+  onChange,
+  disabled = false,
+  inheritLabel,
+}: ExpirationPeriodPickerProps) => {
+  const { _ } = useLingui();
+
+  const mode = getMode(value);
+  const amount = getAmount(value);
+  const unit = getUnit(value);
+
+  const onModeChange = (newMode: string) => {
+    if (newMode === 'inherit') {
+      onChange(null);
+      return;
+    }
+
+    if (newMode === 'disabled') {
+      onChange({ disabled: true });
+      return;
+    }
+
+    onChange({ unit, amount });
+  };
+
+  const onAmountChange = (newAmount: number) => {
+    const clamped = Math.max(1, Math.floor(newAmount));
+
+    onChange({ unit, amount: clamped });
+  };
+
+  const onUnitChange = (newUnit: string) => {
+    // eslint-disable-next-line @typescript-eslint/consistent-type-assertions
+    onChange({ unit: newUnit as TEnvelopeExpirationDurationPeriod['unit'], amount });
+  };
+
+  return (
+    <div className="flex flex-col gap-2">
+      <Select value={mode} onValueChange={onModeChange} disabled={disabled}>
+        <SelectTrigger className="bg-background">
+          <SelectValue />
+        </SelectTrigger>
+
+        <SelectContent>
+          <SelectItem value="duration">
+            <Trans>Custom duration</Trans>
+          </SelectItem>
+
+          <SelectItem value="disabled">
+            <Trans>Never expires</Trans>
+          </SelectItem>
+
+          {inheritLabel !== undefined && <SelectItem value="inherit">{inheritLabel}</SelectItem>}
+        </SelectContent>
+      </Select>
+
+      {mode === 'duration' && (
+        <div className="flex flex-row gap-2">
+          <Input
+            type="number"
+            min={1}
+            className="w-20 bg-background"
+            value={amount}
+            onChange={(e) => onAmountChange(Number(e.target.value))}
+            disabled={disabled}
+          />
+
+          <Select value={unit} onValueChange={onUnitChange} disabled={disabled}>
+            <SelectTrigger className="flex-1 bg-background">
+              <SelectValue />
+            </SelectTrigger>
+
+            <SelectContent>
+              {EXPIRATION_UNITS.map((u) => (
+                <SelectItem key={u.value} value={u.value}>
+                  {_(u.label)}
+                </SelectItem>
+              ))}
+            </SelectContent>
+          </Select>
+        </div>
+      )}
+    </div>
+  );
+};