diff --git a/server/QMax.Api/Controllers/ChatsController.cs b/server/QMax.Api/Controllers/ChatsController.cs
index 0af3afd..1a9ca47 100644
--- a/server/QMax.Api/Controllers/ChatsController.cs
+++ b/server/QMax.Api/Controllers/ChatsController.cs
@@ -805,7 +805,8 @@ public sealed class ChatsController(
 
     private static bool IsChatOpenFailure(string? error)
     {
-        return error?.Contains("not found or did not open", StringComparison.OrdinalIgnoreCase) == true;
+        return error?.Contains("not found or did not open", StringComparison.OrdinalIgnoreCase) == true ||
+            error?.Contains("menu was not opened", StringComparison.OrdinalIgnoreCase) == true;
     }
 
     private async Task<List<Chat>> LoadChatsWithAttachmentsAsync(IReadOnlyCollection<Guid> chatIds, CancellationToken cancellationToken)
diff --git a/tests/QMax.Tests/ApiSmokeTests.cs b/tests/QMax.Tests/ApiSmokeTests.cs
index 62aacb4..18e4351 100644
--- a/tests/QMax.Tests/ApiSmokeTests.cs
+++ b/tests/QMax.Tests/ApiSmokeTests.cs
@@ -682,6 +682,45 @@ public sealed class ApiSmokeTests : IDisposable
         Assert.DoesNotContain(chats!, x => x.Id == chat.Id);
     }
 
+    [Fact]
+    public async Task BulkDeleteRefreshesStaleChatUrlAfterMenuOpenFailure()
+    {
+        const string externalId = "stale-menu-url-chat";
+        const string staleUrl = "https://max.test/chat/wrong-chat";
+        var bridge = new ResolvingDeleteMaxBridgeClient(staleUrl);
+        using var factory = _factory.WithWebHostBuilder(builder =>
+        {
+            builder.ConfigureServices(services =>
+            {
+                services.RemoveAll<IMaxBridgeClient>();
+                services.AddSingleton<IMaxBridgeClient>(bridge);
+            });
+        });
+        using var client = factory.CreateClient();
+        await LoginAsync(client);
+
+        var chat = await CreateDirectChatAsync(client, externalId, "Stale Menu Url");
+        await using (var scope = factory.Services.CreateAsyncScope())
+        {
+            var db = scope.ServiceProvider.GetRequiredService<QMaxDbContext>();
+            var stored = await db.Chats.SingleAsync(x => x.Id == chat.Id);
+            stored.WebUrl = staleUrl;
+            await db.SaveChangesAsync();
+        }
+
+        var response = await client.PostAsJsonAsync(
+            "/api/chats/delete",
+            new ChatBulkActionRequest([chat.Id]),
+            JsonOptions);
+        await AssertStatusAsync(HttpStatusCode.NoContent, response);
+
+        Assert.Equal(externalId, bridge.ResolvedExternalId);
+        Assert.Equal([staleUrl, $"https://max.test/chat/{externalId}"], bridge.DeleteChatUrls);
+
+        var chats = await client.GetFromJsonAsync<ChatDto[]>("/api/chats", JsonOptions);
+        Assert.DoesNotContain(chats!, x => x.Id == chat.Id);
+    }
+
     [Fact]
     public async Task FailedMaxTextSendMarksLocalMessageFailed()
     {
@@ -1457,8 +1496,16 @@ public sealed class ApiSmokeTests : IDisposable
 
     private sealed class ResolvingDeleteMaxBridgeClient : IMaxBridgeClient
     {
+        private readonly string? _staleUrlToReject;
+
+        public ResolvingDeleteMaxBridgeClient(string? staleUrlToReject = null)
+        {
+            _staleUrlToReject = staleUrlToReject;
+        }
+
         public string? ResolvedExternalId { get; private set; }
         public string? DeleteChatUrl { get; private set; }
+        public List<string?> DeleteChatUrls { get; } = [];
 
         public Task<MaxBridgeStatus> GetStatusAsync(CancellationToken cancellationToken)
         {
@@ -1508,7 +1555,13 @@ public sealed class ApiSmokeTests : IDisposable
 
         public Task<MaxActionResult> DeleteChatAsync(string externalChatId, string? chatUrl, CancellationToken cancellationToken)
         {
+            DeleteChatUrls.Add(chatUrl);
             DeleteChatUrl = chatUrl;
+            if (string.Equals(chatUrl, _staleUrlToReject, StringComparison.Ordinal))
+            {
+                return Task.FromResult(new MaxActionResult(false, "MAX chat menu was not opened."));
+            }
+
             return Task.FromResult(string.IsNullOrWhiteSpace(chatUrl)
                 ? new MaxActionResult(false, "MAX chat was not found or did not open.")
                 : new MaxActionResult(true, null));