How to re-enable "Switch to Plan Mode" countdown/reminder?

Where does the bug appear (feature/product)?

Cursor IDE

Describe the Bug

Hi everyone,

I recently saw a new feature where, when using Agent Mode for a complex request, Cursor would show a countdown/reminder pausing the reply to suggest switching to Plan Mode.

I accidentally clicked the option to “skip” or “don’t show this again” (making it auto-skip the countdown), but I actually found that pause helpful and want to bring it back.

I’ve checked the settings but can’t find the specific toggle to reset this behavior. Does anyone know where I can re-enable the “Switch to Plan Mode” reminder/countdown?

Thanks!

Steps to Reproduce

  1. Open Cursor and ensure you are in Agent Mode.
  2. Type a complex or multi-step request (e.g., “Refactor this entire module”) that typically triggers the “Switch to Plan Mode” suggestion.
  3. When the countdown/reminder pop-up appeared, I clicked the option to “Don’t show again” (or “Always skip”).
  4. Now, when I make similar complex requests, the reminder no longer appears.
  5. I have checked Cursor Settings but cannot find a toggle to reset or re-enable this notification.

Operating System

MacOS

Current Cursor Version (Menu → About Cursor → Copy)

Version: 2.3.35
VSCode Version: 1.105.1
Commit: cf8353edc265f5e46b798bfb276861d0bf3bf120
Date: 2026-01-13T07:39:18.564Z
Electron: 37.7.0
Chromium: 138.0.7204.251
Node.js: 22.20.0
V8: 13.8.258.32-electron.0
OS: Darwin x64 24.6.0

For AI issues: which model did you use?

Gemini Pro

Does this stop you from using Cursor

No - Cursor works, but with this issue

Go to Cursor Settings > General and look for “Reset ‘Don’t Ask Again’ Dialogs” - click Show to restore all dismissed prompts, including the Plan Mode suggestion.

This should bring back the countdown/reminder you’re looking for!

I tried that, and after clicking the [show] button it says:

No hidden dialogs yet - You haven’t mark any dialogs as “Don’t ask again“. Any hidden dialogs will appear here to manage.

And the “switch to plan mode countdown/reminder“ still not back.

You’re on version 2.3.35, but Cursor 2.4 is now available. It includes improvements to agent clarification questions and Plan Mode behavior. Try updating via Cursor > Check for Updates

Let us know if the issue persists after updating!

I’m on 2.4.28, and I’m having the same issue (no hidden dialogs yet, but the switch to plan mode is always skipped).

I can report that I’m having the exact same issue as originally mentioned here.

Version: 2.4.31 (Universal)
VSCode Version: 1.105.1
Commit: 3578107fdf149b00059ddad37048220e41681000
Date: 2026-02-08T07:42:24.999Z
Build Type: Stable
Release Track: Default
Electron: 39.2.7
Chromium: 142.0.7444.235
Node.js: 22.21.1
V8: 14.2.231.21-electron.0
OS: Darwin arm64 25.0.0

Can you check if this is empty in Settings → Agents?