diff --git a/apps/dashboard/src/routes/api/polar/webhook/+server.ts b/apps/dashboard/src/routes/api/polar/webhook/+server.ts
index edc335b9..65741fb2 100644
--- a/apps/dashboard/src/routes/api/polar/webhook/+server.ts
+++ b/apps/dashboard/src/routes/api/polar/webhook/+server.ts
@@ -157,6 +157,16 @@ async function onPayload(payload: PolarWebhookPayload) {
     case 'subscription.active':
       break;
     case 'subscription.revoked':
+      try {
+        const result = await OrgPlanApiServer.cancelOrgPlan({
+          subscriptionId,
+          payload: data as unknown as Record<string, unknown>
+        });
+        console.log('Subscription revoked', result);
+      } catch (error) {
+        console.error('Error revoking org plan', error);
+      }
+
       break;
     case 'subscription.canceled':
       break;
diff --git a/packages/db/package.json b/packages/db/package.json
index 6bafcee5..ba15865d 100644
--- a/packages/db/package.json
+++ b/packages/db/package.json
@@ -71,6 +71,7 @@
     "db:backfill-profile-email-verification": "tsx src/scripts/backfill-profile-email-verification.ts",
     "db:update-user-email": "tsx src/scripts/update-user-email.ts",
     "db:notify-students-over-limit": "tsx src/scripts/notify-students-over-limit.ts",
+    "db:downgrade-expired-subscriptions": "tsx src/scripts/downgrade-expired-subscriptions.ts",
     "move-users": "tsx src/scripts/supabase-to-betterauth.ts",
     "pull": "drizzle-kit pull --config drizzle.config.ts",
     "generate-types": "tsx scripts/generate-types.ts && pnpm format",
diff --git a/packages/db/src/queries/organization/organization.ts b/packages/db/src/queries/organization/organization.ts
index d94c7b72..d76b1519 100644
--- a/packages/db/src/queries/organization/organization.ts
+++ b/packages/db/src/queries/organization/organization.ts
@@ -8,7 +8,21 @@ import type {
   TOrganization,
   TOrganizationPlan
 } from '@db/types';
-import { and, asc, count, desc, eq, gt, ilike, inArray, isNotNull, notInArray, or, sql } from 'drizzle-orm';
+import {
+  and,
+  asc,
+  count,
+  desc,
+  eq,
+  getTableColumns,
+  gt,
+  ilike,
+  inArray,
+  isNotNull,
+  notInArray,
+  or,
+  sql
+} from 'drizzle-orm';
 
 import { PLAN } from '@cio/utils/plans';
 import { ROLE } from '@cio/utils/constants';
@@ -1007,6 +1021,33 @@ export const getOrganizationPlanBySubscriptionId = async (
   }
 };
 
+/**
+ * Gets every active organization plan that has a Polar subscription ID attached.
+ * Used by one-off backfills that need to re-verify subscription status against Polar.
+ * @param dbClient Optional DB or transaction client for use within transactions
+ * @returns Active organization plans with org name/siteName for readable logging
+ */
+export const getActiveOrganizationPlansWithSubscription = async (
+  dbClient: DbOrTxClient = db
+): Promise<Array<TOrganizationPlan & { orgName: string; orgSiteName: string | null }>> => {
+  try {
+    return await dbClient
+      .select({
+        ...getTableColumns(schema.organizationPlan),
+        orgName: schema.organization.name,
+        orgSiteName: schema.organization.siteName
+      })
+      .from(schema.organizationPlan)
+      .innerJoin(schema.organization, eq(schema.organization.id, schema.organizationPlan.orgId))
+      .where(and(eq(schema.organizationPlan.isActive, true), isNotNull(schema.organizationPlan.subscriptionId)));
+  } catch (error) {
+    console.error('getActiveOrganizationPlansWithSubscription error:', error);
+    throw new Error(
+      `Failed to fetch active organization plans: ${error instanceof Error ? error.message : 'Unknown error'}`
+    );
+  }
+};
+
 export const createOrganizationPlan = async (
   data: TNewOrganizationPlan,
   dbClient: DbOrTxClient = db
diff --git a/packages/db/src/scripts/downgrade-expired-subscriptions.ts b/packages/db/src/scripts/downgrade-expired-subscriptions.ts
new file mode 100644
index 00000000..50ef8fd2
--- /dev/null
+++ b/packages/db/src/scripts/downgrade-expired-subscriptions.ts
@@ -0,0 +1,96 @@
+/**
+ * One-time (manual, not cron) backfill: for every org with an `organization_plan`
+ * row still marked active, re-check the real subscription status with Polar and
+ * downgrade (deactivate the plan row) any whose subscription has actually ended
+ * — covers subscriptions that expired or didn't renew before the webhook handler
+ * started reacting to `subscription.revoked`. Dry-run by default; pass --execute
+ * to actually deactivate.
+ *
+ * Usage:
+ *   pnpm db:downgrade-expired-subscriptions             # dry run (default)
+ *   pnpm db:downgrade-expired-subscriptions -- --execute # deactivate
+ *
+ * Env:
+ *   POLAR_ACCESS_TOKEN - required
+ *   POLAR_SERVER        - "production" (default) or "sandbox"
+ */
+import 'dotenv/config';
+
+import {
+  cancelOrganizationPlan,
+  getActiveOrganizationPlansWithSubscription
+} from '../queries/organization/organization';
+
+const POLAR_SERVER = process.env.POLAR_SERVER === 'sandbox' ? 'sandbox' : 'production';
+const POLAR_API_BASE = POLAR_SERVER === 'sandbox' ? 'https://sandbox-api.polar.sh' : 'https://api.polar.sh';
+
+async function fetchSubscription(subscriptionId: string, accessToken: string): Promise<Record<string, unknown>> {
+  const response = await fetch(`${POLAR_API_BASE}/v1/subscriptions/${subscriptionId}`, {
+    headers: { Authorization: `Bearer ${accessToken}` }
+  });
+
+  if (!response.ok) {
+    throw new Error(`Polar responded ${response.status} for subscription ${subscriptionId}`);
+  }
+
+  return response.json();
+}
+
+async function main() {
+  const execute = process.argv.includes('--execute');
+  const accessToken = process.env.POLAR_ACCESS_TOKEN;
+
+  if (!accessToken) {
+    throw new Error('POLAR_ACCESS_TOKEN is required');
+  }
+
+  console.log(`Checking active org plans against Polar (${POLAR_SERVER})...`);
+
+  const activePlans = await getActiveOrganizationPlansWithSubscription();
+
+  let downgraded = 0;
+  let stillActive = 0;
+  let errored = 0;
+
+  for (const plan of activePlans) {
+    const subscriptionId = plan.subscriptionId;
+
+    if (!subscriptionId) continue;
+
+    try {
+      const subscription = await fetchSubscription(subscriptionId, accessToken);
+
+      if (subscription.status === 'active') {
+        stillActive++;
+        continue;
+      }
+
+      console.log(
+        `${execute ? 'Downgrading' : '[dry-run] Would downgrade'} ${plan.orgName} (${plan.orgId}): ` +
+          `subscription ${subscriptionId} is "${subscription.status}"`
+      );
+
+      if (execute) {
+        await cancelOrganizationPlan(subscriptionId, subscription);
+      }
+
+      downgraded++;
+    } catch (error) {
+      errored++;
+      console.error(`Skipping ${plan.orgName} (${plan.orgId}): ${error instanceof Error ? error.message : error}`);
+    }
+  }
+
+  console.log(
+    `\nChecked ${activePlans.length} active org plan(s): ${stillActive} still active, ` +
+      `${downgraded} to downgrade${errored ? `, ${errored} error(s)` : ''}.`
+  );
+  console.log(execute ? `Done. Downgraded ${downgraded} org(s).` : 'Dry run — re-run with --execute to downgrade.');
+}
+
+main()
+  .then(() => process.exit(0))
+  .catch((error) => {
+    console.error(error);
+    process.exit(1);
+  });