diff --git a/worker/index.js b/worker/index.js
index dfb6c4f97..85019f8f7 100644
--- a/worker/index.js
+++ b/worker/index.js
@@ -5,7 +5,7 @@ import createPrisma from '@/lib/create-prisma'
 import {
   checkInvoice, checkPendingDeposits, checkPendingWithdrawals,
   checkWithdrawal,
-  finalizeHodlInvoice, subscribeToWallet
+  finalizeHodlInvoice, retryTimeout, subscribeToWallet
 } from './wallet'
 import { repin } from './repin'
 import { trust } from './trust'
@@ -101,6 +101,7 @@ async function work () {
     await boss.work('autoDropBolt11s', jobWrapper(autoDropBolt11s))
     await boss.work('autoWithdraw', jobWrapper(autoWithdraw))
     await boss.work('checkInvoice', jobWrapper(checkInvoice))
+    await boss.work('retryTimeout', jobWrapper(retryTimeout))
     await boss.work('checkWithdrawal', jobWrapper(checkWithdrawal))
     // paidAction jobs
     await boss.work('paidActionForwarding', jobWrapper(paidActionForwarding))
diff --git a/worker/paidAction.js b/worker/paidAction.js
index 9b3ecb5a6..4723352de 100644
--- a/worker/paidAction.js
+++ b/worker/paidAction.js
@@ -1,7 +1,7 @@
 import { getPaymentFailureStatus, hodlInvoiceCltvDetails, getPaymentOrNotSent } from '@/api/lnd'
 import { paidActions } from '@/api/paidAction'
 import { walletLogger } from '@/api/resolvers/wallet'
-import { LND_PATHFINDING_TIME_PREF_PPM, LND_PATHFINDING_TIMEOUT_MS, PAID_ACTION_TERMINAL_STATES } from '@/lib/constants'
+import { LND_PATHFINDING_TIME_PREF_PPM, LND_PATHFINDING_TIMEOUT_MS, PAID_ACTION_TERMINAL_STATES, WALLET_RETRY_BEFORE_MS } from '@/lib/constants'
 import { formatMsats, formatSats, msatsToSats, toPositiveNumber } from '@/lib/format'
 import { datePivot } from '@/lib/time'
 import { Prisma } from '@prisma/client'
@@ -466,9 +466,19 @@ export async function paidActionFailed ({ data: { invoiceId, ...args }, models,
 
       await paidActions[dbInvoice.actionType].onFail?.({ invoice: dbInvoice }, { models, tx, lnd })
 
+      const cancelledAt = new Date()
+
+      // XXX update invoice after retry timeout for notification indicator
+      await models.$executeRaw`
+        INSERT INTO pgboss.job (name, data, retrylimit, retrybackoff, startafter, keepuntil, priority)
+        VALUES ('retryTimeout',
+          jsonb_build_object('hash', ${dbInvoice.hash}::TEXT), 21, true,
+            ${cancelledAt}::TIMESTAMP WITH TIME ZONE + ${`${WALLET_RETRY_BEFORE_MS} milliseconds`}::interval,
+            ${cancelledAt}::TIMESTAMP WITH TIME ZONE + ${`${2 * WALLET_RETRY_BEFORE_MS} milliseconds`}::interval, 100)`
+
       return {
         cancelled: true,
-        cancelledAt: new Date()
+        cancelledAt
       }
     },
     ...args
diff --git a/worker/wallet.js b/worker/wallet.js
index ac09c7ac4..f60581887 100644
--- a/worker/wallet.js
+++ b/worker/wallet.js
@@ -161,6 +161,10 @@ export async function checkInvoice ({ data: { hash, invoice }, boss, models, lnd
   }
 }
 
+export async function retryTimeout ({ data: { hash }, models, lnd, boss }) {
+  await models.invoice.update({ where: { hash }, data: { updatedAt: new Date() } })
+}
+
 async function subscribeToWithdrawals (args) {
   const { lnd } = args