diff --git a/packages/lib/jobs/client.ts b/packages/lib/jobs/client.ts
index 713d928d8..c0e5aeb55 100644
--- a/packages/lib/jobs/client.ts
+++ b/packages/lib/jobs/client.ts
@@ -5,6 +5,7 @@ import { SEND_PASSWORD_RESET_SUCCESS_EMAIL_JOB_DEFINITION } from './definitions/
 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';
 import { SEND_SIGNING_EMAIL_JOB_DEFINITION } from './definitions/emails/send-signing-email';
+import { SEND_SIGNING_REMINDER_EMAIL_JOB } from './definitions/emails/send-signing-reminder-email';
 import { SEND_TEAM_DELETED_EMAIL_JOB_DEFINITION } from './definitions/emails/send-team-deleted-email';
 import { SEND_TEAM_MEMBER_JOINED_EMAIL_JOB_DEFINITION } from './definitions/emails/send-team-member-joined-email';
 import { SEND_TEAM_MEMBER_LEFT_EMAIL_JOB_DEFINITION } from './definitions/emails/send-team-member-left-email';
@@ -27,6 +28,7 @@ export const jobsClient = new JobClient([
   SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION,
   SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION,
   BULK_SEND_TEMPLATE_JOB_DEFINITION,
+  SEND_SIGNING_REMINDER_EMAIL_JOB,
 ] 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 dce2f652b..d0fbf08e7 100644
--- a/packages/lib/jobs/client/_internal/job.ts
+++ b/packages/lib/jobs/client/_internal/job.ts
@@ -26,16 +26,26 @@ export type TriggerJobOptions<Definitions extends ReadonlyArray<JobDefinition> =
   };
 }[number];
 
+export type CronTrigger<N extends string = string> = {
+  type: 'cron';
+  schedule: string;
+  name: N;
+};
+
+export type EventTrigger<N extends string = string> = {
+  type: 'event';
+  name: N;
+};
+
 // eslint-disable-next-line @typescript-eslint/no-explicit-any
 export type JobDefinition<Name extends string = string, Schema = any> = {
   id: string;
   name: string;
   version: string;
   enabled?: boolean;
-  trigger: {
-    name: Name;
-    schema?: z.ZodType<Schema>;
-  };
+  trigger:
+    | (EventTrigger<Name> & { schema?: z.ZodType<Schema> })
+    | (CronTrigger<Name> & { schema?: z.ZodType<Schema> });
   handler: (options: { payload: Schema; io: JobRunIO }) => Promise<Json | void>;
 };
 
diff --git a/packages/lib/jobs/client/inngest.ts b/packages/lib/jobs/client/inngest.ts
index 95f5d5a6e..0c3c1595a 100644
--- a/packages/lib/jobs/client/inngest.ts
+++ b/packages/lib/jobs/client/inngest.ts
@@ -35,29 +35,53 @@ export class InngestJobProvider extends BaseJobProvider {
   }
 
   public defineJob<N extends string, T>(job: JobDefinition<N, T>): void {
-    console.log('defining job', job.id);
-    const fn = this._client.createFunction(
-      {
-        id: job.id,
-        name: job.name,
-      },
-      {
-        event: job.trigger.name,
-      },
-      async (ctx) => {
-        const io = this.convertInngestIoToJobRunIo(ctx);
+    let fn: InngestFunction.Any;
 
-        // We need to cast to any so we can deal with parsing later.
-        // eslint-disable-next-line @typescript-eslint/consistent-type-assertions, @typescript-eslint/no-explicit-any
-        let payload = ctx.event.data as any;
+    if (job.trigger.type === 'cron') {
+      fn = this._client.createFunction(
+        {
+          id: job.id,
+          name: job.name,
+        },
+        {
+          cron: job.trigger.schedule,
+        },
+        async (ctx) => {
+          const io = this.convertInngestIoToJobRunIo(ctx);
+          const payload: T | undefined = undefined;
 
-        if (job.trigger.schema) {
-          payload = job.trigger.schema.parse(payload);
-        }
+          if (job.trigger.schema) {
+            console.warn(
+              `Job "${job.id}" is cron-triggered but defines a schema. The schema will be ignored. `,
+            );
+          }
 
-        await job.handler({ payload, io });
-      },
-    );
+          await job.handler({ payload: payload as T, io });
+        },
+      );
+    } else {
+      fn = this._client.createFunction(
+        {
+          id: job.id,
+          name: job.name,
+        },
+        {
+          event: job.trigger.name,
+        },
+        async (ctx) => {
+          const io = this.convertInngestIoToJobRunIo(ctx);
+
+          // eslint-disable-next-line @typescript-eslint/consistent-type-assertions, @typescript-eslint/no-explicit-any
+          let payload = ctx.event.data as any;
+
+          if (job.trigger.schema) {
+            payload = job.trigger.schema.parse(payload);
+          }
+
+          await job.handler({ payload, io });
+        },
+      );
+    }
 
     this._functions.push(fn);
   }
diff --git a/packages/lib/jobs/definitions/emails/send-confirmation-email.ts b/packages/lib/jobs/definitions/emails/send-confirmation-email.ts
index ad30dd875..bbbb12b86 100644
--- a/packages/lib/jobs/definitions/emails/send-confirmation-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-confirmation-email.ts
@@ -18,6 +18,7 @@ export const SEND_CONFIRMATION_EMAIL_JOB_DEFINITION = {
   name: 'Send Confirmation Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_CONFIRMATION_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_CONFIRMATION_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-document-cancelled-emails.ts b/packages/lib/jobs/definitions/emails/send-document-cancelled-emails.ts
index ac21d806e..70751e1b4 100644
--- a/packages/lib/jobs/definitions/emails/send-document-cancelled-emails.ts
+++ b/packages/lib/jobs/definitions/emails/send-document-cancelled-emails.ts
@@ -19,6 +19,7 @@ export const SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION = {
   name: 'Send Document Cancelled Emails',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION_ID,
     schema: SEND_DOCUMENT_CANCELLED_EMAILS_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-password-reset-success-email.ts b/packages/lib/jobs/definitions/emails/send-password-reset-success-email.ts
index d73246bb6..a0256575d 100644
--- a/packages/lib/jobs/definitions/emails/send-password-reset-success-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-password-reset-success-email.ts
@@ -17,6 +17,7 @@ export const SEND_PASSWORD_RESET_SUCCESS_EMAIL_JOB_DEFINITION = {
   name: 'Send Password Reset Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_PASSWORD_RESET_SUCCESS_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_PASSWORD_RESET_SUCCESS_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-recipient-signed-email.ts b/packages/lib/jobs/definitions/emails/send-recipient-signed-email.ts
index cb67ceed6..90a68a0b5 100644
--- a/packages/lib/jobs/definitions/emails/send-recipient-signed-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-recipient-signed-email.ts
@@ -18,6 +18,7 @@ export const SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION = {
   name: 'Send Recipient Signed Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_RECIPIENT_SIGNED_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-rejection-emails.ts b/packages/lib/jobs/definitions/emails/send-rejection-emails.ts
index 12deffbf5..64a54b361 100644
--- a/packages/lib/jobs/definitions/emails/send-rejection-emails.ts
+++ b/packages/lib/jobs/definitions/emails/send-rejection-emails.ts
@@ -18,6 +18,7 @@ export const SEND_SIGNING_REJECTION_EMAILS_JOB_DEFINITION = {
   name: 'Send Rejection Emails',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_SIGNING_REJECTION_EMAILS_JOB_DEFINITION_ID,
     schema: SEND_SIGNING_REJECTION_EMAILS_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-signing-email.ts b/packages/lib/jobs/definitions/emails/send-signing-email.ts
index 9df4cf1b2..b84f884d2 100644
--- a/packages/lib/jobs/definitions/emails/send-signing-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-signing-email.ts
@@ -21,6 +21,7 @@ export const SEND_SIGNING_EMAIL_JOB_DEFINITION = {
   name: 'Send Signing Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_SIGNING_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_SIGNING_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-signing-reminder-email.ts b/packages/lib/jobs/definitions/emails/send-signing-reminder-email.ts
new file mode 100644
index 000000000..7a674adc6
--- /dev/null
+++ b/packages/lib/jobs/definitions/emails/send-signing-reminder-email.ts
@@ -0,0 +1,169 @@
+import { createElement } from 'react';
+
+import { msg } from '@lingui/core/macro';
+
+import { mailer } from '@documenso/email/mailer';
+import DocumentInviteEmailTemplate from '@documenso/email/templates/document-invite';
+import { prisma } from '@documenso/prisma';
+import { DocumentStatus, RecipientRole, SendStatus } from '@documenso/prisma/client';
+import { DocumentReminderInterval, SigningStatus } from '@documenso/prisma/generated/types';
+
+import { getI18nInstance } from '../../../client-only/providers/i18n-server';
+import { NEXT_PUBLIC_WEBAPP_URL } from '../../../constants/app';
+import { FROM_ADDRESS, FROM_NAME } from '../../../constants/email';
+import { RECIPIENT_ROLES_DESCRIPTION } from '../../../constants/recipient-roles';
+import { extractDerivedDocumentEmailSettings } from '../../../types/document-email';
+import { renderEmailWithI18N } from '../../../utils/render-email-with-i18n';
+import { shouldSendReminder } from '../../../utils/should-send-reminder';
+import type { JobDefinition, JobRunIO } from '../../client/_internal/job';
+
+export type SendSigningReminderEmailHandlerOptions = {
+  io: JobRunIO;
+};
+
+const SEND_SIGNING_REMINDER_EMAIL_JOB_ID = 'send.signing.reminder.email';
+
+export const SEND_SIGNING_REMINDER_EMAIL_JOB = {
+  id: SEND_SIGNING_REMINDER_EMAIL_JOB_ID,
+  name: 'Send Signing Reminder Email',
+  version: '1.0.0',
+  trigger: {
+    type: 'cron',
+    schedule: '*/5 * * * *',
+    name: SEND_SIGNING_REMINDER_EMAIL_JOB_ID,
+  },
+  handler: async ({ io }) => {
+    const now = new Date();
+
+    const documentWithReminders = await prisma.document.findMany({
+      where: {
+        status: DocumentStatus.PENDING,
+        documentMeta: {
+          reminderInterval: {
+            not: DocumentReminderInterval.NONE,
+          },
+        },
+        deletedAt: null,
+      },
+
+      include: {
+        documentMeta: true,
+        user: true,
+        recipients: {
+          where: {
+            signingStatus: SigningStatus.NOT_SIGNED,
+            role: {
+              not: RecipientRole.CC,
+            },
+          },
+        },
+      },
+    });
+
+    console.log(documentWithReminders);
+
+    for (const document of documentWithReminders) {
+      if (!extractDerivedDocumentEmailSettings(document.documentMeta).recipientSigningRequest) {
+        continue;
+      }
+
+      const { documentMeta } = document;
+      if (!documentMeta) {
+        return;
+      }
+
+      const { reminderInterval, lastReminderSentAt } = documentMeta;
+      if (
+        !shouldSendReminder({
+          reminderInterval,
+          lastReminderSentAt,
+          now,
+        })
+      ) {
+        continue;
+      }
+
+      for (const recipient of document.recipients) {
+        const i18n = await getI18nInstance(document.documentMeta?.language);
+        const recipientActionVerb = i18n
+          ._(RECIPIENT_ROLES_DESCRIPTION[recipient.role].actionVerb)
+          .toLowerCase();
+
+        const emailSubject = i18n._(
+          msg`Reminder: Please ${recipientActionVerb} the document "${document.title}"`,
+        );
+        const emailMessage = i18n._(
+          msg`This is a reminder to ${recipientActionVerb} the document "${document.title}". Please complete this at your earliest convenience.`,
+        );
+
+        const signDocumentLink = `${NEXT_PUBLIC_WEBAPP_URL()}/sign/${recipient.token}`;
+        const assetBaseUrl = NEXT_PUBLIC_WEBAPP_URL() || 'http://localhost:3000';
+
+        const template = createElement(DocumentInviteEmailTemplate, {
+          documentName: document.title,
+          inviterName: document.user.name || undefined,
+          inviterEmail: document.user.email,
+          assetBaseUrl,
+          signDocumentLink,
+          customBody: emailMessage,
+          role: recipient.role,
+          selfSigner: recipient.email === document.user.email,
+        });
+
+        await io.runTask('send-reminder-email', async () => {
+          const [html, text] = await Promise.all([
+            renderEmailWithI18N(template, { lang: document.documentMeta?.language }),
+            renderEmailWithI18N(template, {
+              lang: document.documentMeta?.language,
+              plainText: true,
+            }),
+          ]);
+
+          await mailer.sendMail({
+            to: {
+              name: recipient.name,
+              address: recipient.email,
+            },
+            from: {
+              name: FROM_NAME,
+              address: FROM_ADDRESS,
+            },
+            subject: emailSubject,
+            html,
+            text,
+          });
+        });
+
+        await io.runTask('update-recipient-status', async () => {
+          await prisma.recipient.update({
+            where: { id: recipient.id },
+            data: { sendStatus: SendStatus.SENT },
+          });
+        });
+
+        // TODO: Duncan == Audit log
+        // await io.runTask('store-reminder-audit-log', async () => {
+        //   await prisma.documentAuditLog.create({
+        //     data: createDocumentAuditLogData({
+        //       type: DOCUMENT_AUDIT_LOG_TYPE.REMINDER_SENT,
+        //       documentId: document.id,
+        //       user,
+        //       requestMetadata,
+        //       data: {
+        //         recipientId: recipient.id,
+        //         recipientName: recipient.name,
+        //         recipientEmail: recipient.email,
+        //         recipientRole: recipient.role,
+        //       },
+        //     }),
+        //   });
+        // });
+      }
+
+      await prisma.documentMeta.update({
+        where: { id: document.documentMeta?.id },
+        data: { lastReminderSentAt: now },
+      });
+    }
+  },
+} as const satisfies JobDefinition<typeof SEND_SIGNING_REMINDER_EMAIL_JOB_ID>;
diff --git a/packages/lib/jobs/definitions/emails/send-team-deleted-email.ts b/packages/lib/jobs/definitions/emails/send-team-deleted-email.ts
index 03c32b552..1c5a66372 100644
--- a/packages/lib/jobs/definitions/emails/send-team-deleted-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-team-deleted-email.ts
@@ -46,6 +46,7 @@ export const SEND_TEAM_DELETED_EMAIL_JOB_DEFINITION = {
   name: 'Send Team Deleted Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_TEAM_DELETED_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_TEAM_DELETED_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-team-member-joined-email.ts b/packages/lib/jobs/definitions/emails/send-team-member-joined-email.ts
index 258e7a34e..f11a9a776 100644
--- a/packages/lib/jobs/definitions/emails/send-team-member-joined-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-team-member-joined-email.ts
@@ -18,6 +18,7 @@ export const SEND_TEAM_MEMBER_JOINED_EMAIL_JOB_DEFINITION = {
   name: 'Send Team Member Joined Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_TEAM_MEMBER_JOINED_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_TEAM_MEMBER_JOINED_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/emails/send-team-member-left-email.ts b/packages/lib/jobs/definitions/emails/send-team-member-left-email.ts
index f940896a4..a79cfe738 100644
--- a/packages/lib/jobs/definitions/emails/send-team-member-left-email.ts
+++ b/packages/lib/jobs/definitions/emails/send-team-member-left-email.ts
@@ -18,6 +18,7 @@ export const SEND_TEAM_MEMBER_LEFT_EMAIL_JOB_DEFINITION = {
   name: 'Send Team Member Left Email',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEND_TEAM_MEMBER_LEFT_EMAIL_JOB_DEFINITION_ID,
     schema: SEND_TEAM_MEMBER_LEFT_EMAIL_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/internal/bulk-send-template.ts b/packages/lib/jobs/definitions/internal/bulk-send-template.ts
index c101e3c40..3787057a5 100644
--- a/packages/lib/jobs/definitions/internal/bulk-send-template.ts
+++ b/packages/lib/jobs/definitions/internal/bulk-send-template.ts
@@ -23,6 +23,7 @@ export const BULK_SEND_TEMPLATE_JOB_DEFINITION = {
   name: 'Bulk Send Template',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: BULK_SEND_TEMPLATE_JOB_DEFINITION_ID,
     schema: BULK_SEND_TEMPLATE_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/jobs/definitions/internal/seal-document.ts b/packages/lib/jobs/definitions/internal/seal-document.ts
index 27d922f27..e2d48c20d 100644
--- a/packages/lib/jobs/definitions/internal/seal-document.ts
+++ b/packages/lib/jobs/definitions/internal/seal-document.ts
@@ -19,6 +19,7 @@ export const SEAL_DOCUMENT_JOB_DEFINITION = {
   name: 'Seal Document',
   version: '1.0.0',
   trigger: {
+    type: 'event',
     name: SEAL_DOCUMENT_JOB_DEFINITION_ID,
     schema: SEAL_DOCUMENT_JOB_DEFINITION_SCHEMA,
   },
diff --git a/packages/lib/utils/should-send-reminder.ts b/packages/lib/utils/should-send-reminder.ts
new file mode 100644
index 000000000..91666fd14
--- /dev/null
+++ b/packages/lib/utils/should-send-reminder.ts
@@ -0,0 +1,49 @@
+import { DateTime } from 'luxon';
+
+import { DocumentReminderInterval } from '@documenso/prisma/client';
+
+export type ShouldSendReminderOptions = {
+  reminderInterval: DocumentReminderInterval;
+  lastReminderSentAt: Date | null;
+  now: Date;
+};
+
+export const shouldSendReminder = ({
+  lastReminderSentAt,
+  now = new Date(),
+  reminderInterval,
+}: ShouldSendReminderOptions): boolean => {
+  if (!lastReminderSentAt) {
+    return true;
+  }
+
+  const hoursSinceLastReminder = DateTime.fromJSDate(now).diff(
+    DateTime.fromJSDate(lastReminderSentAt),
+    'hours',
+  ).hours;
+  const monthsSinceLastReminder = DateTime.fromJSDate(now).diff(
+    DateTime.fromJSDate(lastReminderSentAt),
+    'months',
+  ).months;
+
+  switch (reminderInterval) {
+    case DocumentReminderInterval.EVERY_1_HOUR:
+      return hoursSinceLastReminder >= 1;
+    case DocumentReminderInterval.EVERY_6_HOURS:
+      return hoursSinceLastReminder >= 6;
+    case DocumentReminderInterval.EVERY_12_HOURS:
+      return hoursSinceLastReminder >= 12;
+    case DocumentReminderInterval.DAILY:
+      return hoursSinceLastReminder >= 24;
+    case DocumentReminderInterval.EVERY_3_DAYS:
+      return hoursSinceLastReminder >= 72;
+    case DocumentReminderInterval.WEEKLY:
+      return hoursSinceLastReminder >= 168;
+    case DocumentReminderInterval.EVERY_2_WEEKS:
+      return hoursSinceLastReminder >= 336;
+    case DocumentReminderInterval.MONTHLY:
+      return monthsSinceLastReminder >= 1;
+    default:
+      return false;
+  }
+};