Personal Skills do not sync between ChatGPT Work on Web/iOS and the Windows desktop app

What issue are you seeing?

Personal Skills are not synchronized consistently across ChatGPT Work surfaces when using the same OpenAI account.

I use the same account across:

• ChatGPT on iOS
• ChatGPT Web in Chrome and Edge
• The ChatGPT desktop app on Windows

Personal Skills created, added, updated, or deleted through ChatGPT Web/iOS are reflected across the account-based web/mobile experience, but they do not synchronize with the Personal Skills stored and used by the Windows desktop app.

The Windows desktop app appears to rely on its local skill files, effectively creating a separate Personal Skills library from the account-level library available on Web/iOS.

The opposite direction has the same problem: if I add or modify a Personal Skill locally in the Windows desktop app or directly in its local skills directory, that change does not propagate back to my OpenAI account, ChatGPT Web, or the iOS app.

As a result, the same OpenAI account can have two different versions of its Personal Skills library depending on which ChatGPT surface is being used.

This creates version drift, duplicate copies, inconsistent updates/deletions, and requires manually transferring skill files between devices.

What steps can reproduce the bug?

Scenario 1 — Add a Personal Skill on iOS

1. Sign in to the ChatGPT iOS app with an OpenAI account.
2. Open Work and add/create a Personal Skill.
3. Confirm that the skill is available from the account on the supported web/mobile experience.
4. On Windows, sign in to the ChatGPT desktop app using the exact same OpenAI account.
5. Open Work / Personal Skills.
6. The newly added Personal Skill is not synchronized into the local Personal Skills library used by the Windows desktop app.

Scenario 2 — Add a Personal Skill on ChatGPT Web

1. Sign in to ChatGPT Web in Chrome or Edge.
2. Open Work and add/create a Personal Skill.
3. Confirm that the skill is associated with the account.
4. Open the ChatGPT Windows desktop app with the same account.
5. The skill does not automatically appear in the Windows desktop Personal Skills library.

Scenario 3 — Add a Personal Skill locally on Windows

1. Open the ChatGPT desktop app on Windows.
2. Add a Personal Skill locally, either through Work or through the local Personal Skills file location used by the desktop app.
3. Confirm that the skill works in the Windows desktop app.
4. Open ChatGPT Web with the same account.
5. Check Personal Skills.
6. The locally installed skill is not synchronized to the account.
7. Open the ChatGPT iOS app with the same account.
8. The locally installed skill is also unavailable there.

Scenario 4 — Update an existing skill

1. Have the same skill available on both sides after manually copying it.
2. Edit/update the skill on ChatGPT Web or iOS.
3. Open the Windows desktop app.
4. The local Windows copy remains unchanged.

The reverse also occurs:

1. Edit the local Windows copy.
2. Open ChatGPT Web/iOS.
3. The account-level copy is not updated.

This can leave two different versions of the same Personal Skill.

Scenario 5 — Delete a skill

1. Have a Personal Skill available on both sides after manually transferring it.
2. Delete the skill from the account/web/mobile side.
3. Open the Windows desktop app.
4. The local copy may still remain available.

Likewise, deleting a local Windows skill does not remove the account-level version from Web/iOS.

Current workaround

To use a skill created from Web/iOS on Windows, I currently have to:

1. Ask ChatGPT/Work to give me the skill files.
2. Export/download the files.
3. Upload them to cloud storage such as Google Drive.
4. Download them again on the Windows PC.
5. Manually import them into the Windows ChatGPT desktop app or place them into the local skills directory.

If I later update the skill from Web/iOS, I may need to repeat this process again manually.

This behavior is reproducible using the same OpenAI account across these surfaces.

What is the expected behavior?

Personal Skills should remain synchronized across supported ChatGPT Work surfaces when they belong to the same OpenAI account.

For example:

• Adding a Personal Skill on iOS should make it available on ChatGPT Web and the Windows desktop app.
• Adding a Personal Skill from ChatGPT Web should make it available on iOS and Windows.
• Adding a Personal Skill from the Windows desktop app should associate it with the account and make it available on Web/iOS.
• Updating a Personal Skill on one device should propagate the updated version to the other supported devices.
• Deleting a Personal Skill should synchronize that deletion across the account.
• Renaming or changing the state of a skill should remain consistent across devices.

If the Windows desktop app requires skills to physically exist as local files, it should automatically download/materialize the account-level skill into its local Personal Skills directory.

Likewise, changes made to an account-synchronized Personal Skill from the Windows desktop app should be uploaded back to the account.

If the same skill is independently modified on multiple devices before synchronization completes, the application should detect the conflict rather than silently overwriting one version.

Ideally, ChatGPT could distinguish between:

• Account-synced Personal Skills
• Local-only Personal Skills
• Project/repository-specific Skills

This would still allow deliberately local skills while keeping normal Personal Skills synchronized across the user's account.

Additional information

Environment tested:

• Same OpenAI account on all devices
• ChatGPT iOS app on an iPhone 14 Pro
• ChatGPT Web using Chrome and Edge
• ChatGPT desktop app on Windows
• ChatGPT Work / Personal Skills

The issue is especially noticeable because Web/iOS behave like account-based surfaces, while the Windows desktop implementation depends on local skill files.

From a user's perspective, Personal Skills appear to be an account-level customization, so having a separate unsynchronized desktop library is unexpected.

This becomes increasingly problematic when maintaining several custom skills because it is difficult to know which copy is currently the newest version.

A synchronization mechanism could still preserve local filesystem access on desktop. The account copy could act as the canonical/synchronized version, while the desktop client keeps a local representation that is downloaded and updated automatically.

For skills containing functionality that cannot run on mobile/web, the skill could still remain synchronized while unsupported functionality is marked as unavailable on that surface, instead of requiring a completely separate copy.

I can provide additional screenshots, sample skill files, or exact before/after examples if needed.

Start by tracing the Windows desktop app's local Personal Skills directory and the account-backed Work/Personal Skills flows described in the reproduction scenarios. Reproduce changes in both directions, then verify that additions, updates, deletions, renames, and conflicts remain consistent across Windows, Web, and iOS without manual file transfer.