diff --git a/apps/web/pages/documents/[id]/sign.tsx b/apps/web/pages/documents/[id]/sign.tsx
index 48b054572..0a62e1f7c 100644
--- a/apps/web/pages/documents/[id]/sign.tsx
+++ b/apps/web/pages/documents/[id]/sign.tsx
@@ -3,6 +3,10 @@ import Head from "next/head";
 import { NextPageWithLayout } from "../../_app";
 import { ReadStatus } from "@prisma/client";
 import PDFSigner from "../../../components/editor/pdf-signer";
+import Logo from "../../../components/logo";
+import Link from "next/link";
+import { Button } from "@documenso/ui";
+import { CheckBadgeIcon, ClockIcon } from "@heroicons/react/24/outline";
 
 const SignPage: NextPageWithLayout = (props: any) => {
   return (
@@ -10,7 +14,49 @@ const SignPage: NextPageWithLayout = (props: any) => {
       <Head>
         <title>Sign | Documenso</title>
       </Head>
-      <PDFSigner document={props.document} fields={props.fields} />
+      {!props.expired ? (
+        <PDFSigner document={props.document} fields={props.fields} />
+      ) : (
+        <>
+          <div className="mx-auto w-fit px-4 py-16 sm:px-6 sm:py-24 lg:px-8">
+            <ClockIcon className="text-neon w-10 inline mr-1"></ClockIcon>
+            <h1 className="text-base font-medium text-neon inline align-middle">
+              Time flies.
+            </h1>
+            <p className="mt-2 text-4xl font-bold tracking-tight">
+              This signing link is expired.
+            </p>
+            <p className="mt-2 text-base text-gray-500">
+              Please ask{" "}
+              {props.document.User.name
+                ? `${props.document.User.name}`
+                : `the sender`}{" "}
+              to resend it.
+            </p>
+            <div className="mx-auto w-fit text-xl pt-20"></div>
+          </div>
+          <div>
+            <div className="relative mx-96">
+              <div
+                className="absolute inset-0 flex items-center"
+                aria-hidden="true"
+              >
+                <div className="w-full border-t border-gray-300" />
+              </div>
+              <div className="relative flex justify-center"></div>
+            </div>
+          </div>
+          <p className="mt-4 text-center text-sm text-gray-600">
+            Want to send of your own?{" "}
+            <Link
+              href="/signup?source=expired"
+              className="font-medium text-neon hover:text-neon"
+            >
+              Create your own Account
+            </Link>
+          </p>
+        </>
+      )}
     </>
   );
 };
@@ -34,7 +80,7 @@ export async function getServerSideProps(context: any) {
       token: recipientToken,
     },
     include: {
-      Document: true,
+      Document: { include: { User: true } },
     },
   });
 
@@ -61,8 +107,11 @@ export async function getServerSideProps(context: any) {
 
   return {
     props: {
-      document: recipient.Document,
-      fields: unsignedFields,
+      document: JSON.parse(JSON.stringify(recipient.Document)),
+      fields: JSON.parse(JSON.stringify(unsignedFields)),
+      expired: recipient.expired
+        ? new Date(recipient.expired) < new Date()
+        : false,
     },
   };
 }
diff --git a/packages/lib/mail/sendSigningRequest.ts b/packages/lib/mail/sendSigningRequest.ts
index d042b9a82..e947149e6 100644
--- a/packages/lib/mail/sendSigningRequest.ts
+++ b/packages/lib/mail/sendSigningRequest.ts
@@ -23,11 +23,19 @@ export const sendSigningRequest = async (
   ).catch((err) => {
     throw err;
   });
+
+  const expiryDate = new Date();
+  expiryDate.setDate(expiryDate.getDate() + 60);
+
   await prisma.recipient.update({
     where: {
       id: recipient.id,
     },
-    data: { sendStatus: SendStatus.SENT, readStatus: ReadStatus.NOT_OPENED },
+    data: {
+      sendStatus: SendStatus.SENT,
+      readStatus: ReadStatus.NOT_OPENED,
+      expired: expiryDate,
+    },
   });
 
   await prisma.document.update({
diff --git a/packages/prisma/schema.prisma b/packages/prisma/schema.prisma
index 82cc64513..1f450eaeb 100644
--- a/packages/prisma/schema.prisma
+++ b/packages/prisma/schema.prisma
@@ -91,6 +91,7 @@ model Recipient {
   email         String        @db.VarChar(255)
   name          String        @default("") @db.VarChar(255)
   token         String
+  expired       DateTime?
   readStatus    ReadStatus    @default(NOT_OPENED)
   signingStatus SigningStatus @default(NOT_SIGNED)
   sendStatus    SendStatus    @default(NOT_SENT)
