diff --git a/apps/browser/src/_locales/en/messages.json b/apps/browser/src/_locales/en/messages.json
index f8dde376b35..fc708ba9790 100644
--- a/apps/browser/src/_locales/en/messages.json
+++ b/apps/browser/src/_locales/en/messages.json
@@ -3657,6 +3657,9 @@
   "thisRequestIsNoLongerValid": {
     "message": "This request is no longer valid."
   },
+  "thatRequestIsNoLongerValidStartingNewRequest": {
+    "message": "That request is no longer valid. Starting a new request."
+  },
   "loginRequestHasAlreadyExpired": {
     "message": "Login request has already expired."
   },
diff --git a/apps/desktop/src/locales/en/messages.json b/apps/desktop/src/locales/en/messages.json
index 72d40ed750f..e190ad8c5ae 100644
--- a/apps/desktop/src/locales/en/messages.json
+++ b/apps/desktop/src/locales/en/messages.json
@@ -3113,6 +3113,9 @@
   "thisRequestIsNoLongerValid": {
     "message": "This request is no longer valid."
   },
+  "thatRequestIsNoLongerValidStartingNewRequest": {
+    "message": "That request is no longer valid. Starting a new request."
+  },
   "confirmAccessAttempt": {
     "message": "Confirm access attempt for $EMAIL$",
     "placeholders": {
diff --git a/apps/web/src/locales/en/messages.json b/apps/web/src/locales/en/messages.json
index bbd89c1d288..6928b8bfdff 100644
--- a/apps/web/src/locales/en/messages.json
+++ b/apps/web/src/locales/en/messages.json
@@ -3978,6 +3978,9 @@
   "thisRequestIsNoLongerValid": {
     "message": "This request is no longer valid."
   },
+  "thatRequestIsNoLongerValidStartingNewRequest": {
+    "message": "That request is no longer valid. Starting a new request."
+  },
   "loginRequestApprovedForEmailOnDevice": {
     "message": "Login request approved for $EMAIL$ on $DEVICE$",
     "placeholders": {
diff --git a/libs/auth/src/angular/login-via-auth-request/login-via-auth-request.component.ts b/libs/auth/src/angular/login-via-auth-request/login-via-auth-request.component.ts
index f95af8573d0..5ccc221777a 100644
--- a/libs/auth/src/angular/login-via-auth-request/login-via-auth-request.component.ts
+++ b/libs/auth/src/angular/login-via-auth-request/login-via-auth-request.component.ts
@@ -562,13 +562,7 @@ export class LoginViaAuthRequestComponent implements OnInit, OnDestroy {
         );
       }
     } catch (error) {
-      // If the request no longer exists, we treat it as if it's been answered (and denied).
-      if (error instanceof ErrorResponse && error.statusCode === HttpStatusCode.NotFound) {
-        authRequestResponse = undefined;
-        this.logService.error("Auth request response not generated");
-      } else {
-        this.logService.error(error);
-      }
+      this.logService.error(error);
       this.loading = false;
     }
 
@@ -589,6 +583,10 @@ export class LoginViaAuthRequestComponent implements OnInit, OnDestroy {
 
       // Request doesn't exist anymore, so we'll clear the cache and start a new request.
       if (!authRequestResponse) {
+        this.toastService.showToast({
+          variant: "info",
+          message: this.i18nService.t("thatRequestIsNoLongerValidStartingNewRequest"),
+        });
         return await this.clearExistingStandardAuthRequestAndStartNewRequest();
       }
 
@@ -639,11 +637,21 @@ export class LoginViaAuthRequestComponent implements OnInit, OnDestroy {
       return;
     }
 
-    await this.decryptViaApprovedAuthRequest(
-      authRequestResponse,
-      this.authRequestKeyPair.privateKey,
-      userId,
-    );
+    try {
+      await this.decryptViaApprovedAuthRequest(
+        authRequestResponse,
+        this.authRequestKeyPair.privateKey,
+        userId,
+      );
+    } catch (error) {
+      this.logService.error(error);
+      this.toastService.showToast({
+        variant: "info",
+        message: this.i18nService.t("thatRequestIsNoLongerValidStartingNewRequest"),
+      });
+      await this.clearExistingStandardAuthRequestAndStartNewRequest();
+      this.loading = false;
+    }
   }
 
   private async handleUnauthenticatedFlows(