diff --git a/src/_locales/en/messages.json b/src/_locales/en/messages.json
index d113ad87e..e3f4f5e4b 100755
--- a/src/_locales/en/messages.json
+++ b/src/_locales/en/messages.json
@@ -54,6 +54,12 @@
   "keyRevoked_action_reconnectBtn": {
     "message": "Reconnect"
   },
+  "disconnectWallet_error_generic": {
+    "message": "We were unable to disconnect your wallet ($ERROR$).",
+    "placeholders": {
+      "ERROR": { "content": "$1", "example": "Internal server error" }
+    }
+  },
   "pay_action_pay": {
     "message": "Send now"
   },
diff --git a/src/background/services/background.ts b/src/background/services/background.ts
index 2fa1946b2..5cf564061 100644
--- a/src/background/services/background.ts
+++ b/src/background/services/background.ts
@@ -266,12 +266,12 @@ export class Background {
               return;
 
             case 'DISCONNECT_WALLET':
-              await this.walletService.disconnectWallet();
+              await this.walletService.disconnectWallet(message.payload.force);
               this.tabState.clearAllState('disconnect');
               await this.browser.alarms.clear(ALARM_RESET_OUT_OF_FUNDS);
               await this.updateVisualIndicatorsForCurrentTab();
               this.sendToPopup.send('SET_STATE', { state: {}, prevState: {} });
-              return;
+              return success(undefined);
 
             case 'TOGGLE_CONTINUOUS_PAYMENTS': {
               await this.monetizationService.toggleContinuousPayments();
diff --git a/src/background/services/openPayments.ts b/src/background/services/openPayments.ts
index 5ecbcdad0..a16eafd93 100644
--- a/src/background/services/openPayments.ts
+++ b/src/background/services/openPayments.ts
@@ -212,7 +212,7 @@ export class OpenPaymentsService {
   }
 }
 
-const isOpenPaymentsClientError = (error: unknown) =>
+export const isOpenPaymentsClientError = (error: unknown) =>
   error instanceof OpenPaymentsClientError;
 
 export const isKeyRevokedError = (error: unknown) => {
diff --git a/src/background/services/wallet.ts b/src/background/services/wallet.ts
index e8baa7011..a45b36431 100644
--- a/src/background/services/wallet.ts
+++ b/src/background/services/wallet.ts
@@ -23,7 +23,10 @@ import {
 } from '@/background/utils';
 import { KeyAutoAddService } from '@/background/services/keyAutoAdd';
 import { generateEd25519KeyPair, exportJWK } from '@/shared/crypto';
-import { isInvalidClientError } from '@/background/services/openPayments';
+import {
+  isInvalidClientError,
+  isOpenPaymentsClientError,
+} from '@/background/services/openPayments';
 import { APP_URL } from '@/background/constants';
 import { bytesToHex } from '@noble/hashes/utils';
 import type { Cradle } from '@/background/container';
@@ -37,6 +40,7 @@ export class WalletService {
   private storage: Cradle['storage'];
   private events: Cradle['events'];
   private browser: Cradle['browser'];
+  private logger: Cradle['logger'];
   private appName: Cradle['appName'];
   private browserName: Cradle['browserName'];
   private t: Cradle['t'];
@@ -47,6 +51,7 @@ export class WalletService {
     storage,
     events,
     browser,
+    logger,
     appName,
     browserName,
     t,
@@ -57,6 +62,7 @@ export class WalletService {
       storage,
       events,
       browser,
+      logger,
       appName,
       browserName,
       t,
@@ -245,7 +251,7 @@ export class WalletService {
     this.resetConnectState();
   }
 
-  async disconnectWallet() {
+  async disconnectWallet(force = false) {
     const { recurringGrant, oneTimeGrant } = await this.storage.get([
       'recurringGrant',
       'oneTimeGrant',
@@ -253,14 +259,33 @@ export class WalletService {
     if (!recurringGrant && !oneTimeGrant) {
       return;
     }
+
+    const handleError = (
+      err: unknown,
+      grantType: 'recurring' | 'oneTime',
+      force: boolean,
+    ) => {
+      this.logger.error(`Could not cancel ${grantType} grant`, { err });
+      if (force) return;
+
+      if (isOpenPaymentsClientError(err)) {
+        throw new ErrorWithKey('disconnectWallet_error_generic', [
+          err.status ? `HTTP ${err.status} - ${err.message}` : err.message,
+        ]);
+      }
+      throw err;
+    };
+
     if (recurringGrant) {
-      await this.outgoingPaymentGrantService.cancelGrant(
-        recurringGrant.continue,
-      );
+      await this.outgoingPaymentGrantService
+        .cancelGrant(recurringGrant.continue)
+        .catch((err) => handleError(err, 'recurring', force));
       this.outgoingPaymentGrantService.disableRecurringGrant();
     }
     if (oneTimeGrant) {
-      await this.outgoingPaymentGrantService.cancelGrant(oneTimeGrant.continue);
+      await this.outgoingPaymentGrantService
+        .cancelGrant(oneTimeGrant.continue)
+        .catch((err) => handleError(err, 'recurring', force));
       this.outgoingPaymentGrantService.disableOneTimeGrant();
     }
     await this.storage.clear();
diff --git a/src/pages/popup/components/ErrorKeyRevoked.tsx b/src/pages/popup/components/ErrorKeyRevoked.tsx
index 01a0f245b..00d969bf3 100644
--- a/src/pages/popup/components/ErrorKeyRevoked.tsx
+++ b/src/pages/popup/components/ErrorKeyRevoked.tsx
@@ -11,7 +11,7 @@ import type { ReconnectWalletPayload, Response } from '@/shared/messages';
 
 interface Props {
   info: Pick<PopupStore, 'publicKey' | 'walletAddress'>;
-  disconnectWallet: () => Promise<Response>;
+  disconnectWallet: (force: boolean) => Promise<Response>;
   reconnectWallet: (data: ReconnectWalletPayload) => Promise<Response>;
   onReconnect?: () => void;
   onDisconnect?: () => void;
@@ -90,7 +90,7 @@ const MainScreen = ({
     setErrorMsg('');
     try {
       setIsLoading(true);
-      await disconnectWallet();
+      await disconnectWallet(true);
       onDisconnect?.();
     } catch (error) {
       setErrorMsg(error.message);
diff --git a/src/pages/popup/components/Settings/WalletInformation.tsx b/src/pages/popup/components/Settings/WalletInformation.tsx
index 1f66fe816..8a6cd1c13 100644
--- a/src/pages/popup/components/Settings/WalletInformation.tsx
+++ b/src/pages/popup/components/Settings/WalletInformation.tsx
@@ -4,7 +4,8 @@ import { Input } from '@/pages/shared/components/ui/Input';
 import { Label } from '@/pages/shared/components/ui/Label';
 import { Code } from '@/pages/shared/components/ui/Code';
 import { Button } from '@/pages/shared/components/ui/Button';
-import { useMessage } from '@/popup/lib/context';
+import { toErrorInfoFactory } from '@/pages/shared/lib/utils';
+import { useMessage, useTranslation } from '@/popup/lib/context';
 import { ROUTES_PATH } from '@/popup/Popup';
 import { useLocation } from 'wouter';
 import type { PopupStore } from '@/shared/types';
@@ -18,9 +19,32 @@ export const WalletInformation = ({
   publicKey,
   walletAddress,
 }: WalletInformationProps) => {
+  const t = useTranslation();
   const message = useMessage();
   const [_location, navigate] = useLocation();
+  const [disconnectError, setDisconnectError] = React.useState<string>('');
   const [isSubmitting, setIsSubmitting] = React.useState(false);
+  const toErrorInfo = toErrorInfoFactory(t);
+
+  const disconnectWallet = async (force = false) => {
+    setIsSubmitting(true);
+    setDisconnectError('');
+    try {
+      const res = await message.send('DISCONNECT_WALLET', { force });
+      if (!res.success) {
+        if (res.error) {
+          throw new Error(toErrorInfo(res.error)!.message);
+        }
+        throw new Error(res.message);
+      }
+      navigate(ROUTES_PATH.HOME);
+      window.location.reload();
+    } catch (error) {
+      setDisconnectError(error.message);
+    } finally {
+      setIsSubmitting(false);
+    }
+  };
 
   return (
     <div className="flex h-full flex-col gap-8">
@@ -29,10 +53,7 @@ export const WalletInformation = ({
         className="space-y-4"
         onSubmit={async (ev) => {
           ev.preventDefault();
-          setIsSubmitting(true);
-          await message.send('DISCONNECT_WALLET');
-          navigate(ROUTES_PATH.HOME);
-          window.location.reload();
+          await disconnectWallet();
         }}
       >
         <Input
@@ -58,6 +79,19 @@ export const WalletInformation = ({
         >
           Disconnect
         </Button>
+
+        {disconnectError && (
+          <p className="text-sm text-error !mt-1">
+            {disconnectError}
+            <button
+              type="button"
+              onClick={() => disconnectWallet(true)}
+              className="ml-1 inline-block underline"
+            >
+              Force disconnect?
+            </button>
+          </p>
+        )}
       </form>
 
       <details className="border-t">
diff --git a/src/pages/popup/pages/ErrorKeyRevoked.tsx b/src/pages/popup/pages/ErrorKeyRevoked.tsx
index 92753378f..f00d8b9eb 100644
--- a/src/pages/popup/pages/ErrorKeyRevoked.tsx
+++ b/src/pages/popup/pages/ErrorKeyRevoked.tsx
@@ -32,7 +32,7 @@ export default () => {
       info={{ publicKey, walletAddress }}
       reconnectWallet={(data) => message.send('RECONNECT_WALLET', data)}
       onReconnect={onReconnect}
-      disconnectWallet={() => message.send('DISCONNECT_WALLET')}
+      disconnectWallet={(force) => message.send('DISCONNECT_WALLET', { force })}
       onDisconnect={onDisconnect}
     />
   );
diff --git a/src/shared/messages.ts b/src/shared/messages.ts
index 894b0cc2f..52a9bda0c 100644
--- a/src/shared/messages.ts
+++ b/src/shared/messages.ts
@@ -177,7 +177,7 @@ export type PopupToBackgroundMessage = {
     output: never;
   };
   DISCONNECT_WALLET: {
-    input: never;
+    input: { force: boolean };
     output: never;
   };
   TOGGLE_CONTINUOUS_PAYMENTS: {