diff --git a/packages/ee/server-only/stripe/webhook/on-subscription-deleted.ts b/packages/ee/server-only/stripe/webhook/on-subscription-deleted.ts
index c930f70de..494269b26 100644
--- a/packages/ee/server-only/stripe/webhook/on-subscription-deleted.ts
+++ b/packages/ee/server-only/stripe/webhook/on-subscription-deleted.ts
@@ -1,19 +1,89 @@
 import { SubscriptionStatus } from '@prisma/client';
 
+import { createOrganisationClaimUpsertData } from '@documenso/lib/server-only/organisation/create-organisation';
 import type { Stripe } from '@documenso/lib/server-only/stripe';
+import { INTERNAL_CLAIM_ID, internalClaims } from '@documenso/lib/types/subscription';
 import { prisma } from '@documenso/prisma';
 
+import { extractStripeClaimId } from './on-subscription-updated';
+
 export type OnSubscriptionDeletedOptions = {
   subscription: Stripe.Subscription;
 };
 
 export const onSubscriptionDeleted = async ({ subscription }: OnSubscriptionDeletedOptions) => {
-  await prisma.subscription.update({
+  const existingSubscription = await prisma.subscription.findUnique({
     where: {
       planId: subscription.id,
     },
+    include: {
+      organisation: {
+        include: {
+          organisationClaim: true,
+        },
+      },
+    },
+  });
+
+  // If the subscription doesn't exist, we don't need to do anything.
+  if (!existingSubscription) {
+    return;
+  }
+
+  const subscriptionClaimId = await extractClaimIdFromStripeSubscription(subscription);
+
+  // Individuals get their subscription deleted so they can return to the
+  // free plan.
+  if (subscriptionClaimId === INTERNAL_CLAIM_ID.INDIVIDUAL) {
+    await prisma.$transaction(async (tx) => {
+      await tx.subscription.delete({
+        where: {
+          id: existingSubscription.id,
+        },
+      });
+
+      await tx.organisationClaim.update({
+        where: {
+          id: existingSubscription.organisation.organisationClaim.id,
+        },
+        data: {
+          originalSubscriptionClaimId: INTERNAL_CLAIM_ID.FREE,
+          ...createOrganisationClaimUpsertData(internalClaims[INTERNAL_CLAIM_ID.FREE]),
+        },
+      });
+    });
+
+    return;
+  }
+
+  // For all other cases, mark the subscription as inactive since
+  // they should still have a "Personal" account.
+  await prisma.subscription.update({
+    where: {
+      id: existingSubscription.id,
+    },
     data: {
       status: SubscriptionStatus.INACTIVE,
     },
   });
 };
+
+/**
+ * Extracts the claim ID from the Stripe subscription.
+ *
+ * Returns `null` if no claim ID found.
+ */
+const extractClaimIdFromStripeSubscription = async (subscription: Stripe.Subscription) => {
+  const deletedItem = subscription.items.data[0];
+
+  if (!deletedItem) {
+    return null;
+  }
+
+  try {
+    return await extractStripeClaimId(deletedItem.price);
+  } catch (error) {
+    console.error(error);
+    return null;
+  }
+};