Desktop Work local-file access: execution mode and guidance unclear

Summary

While using ChatGPT Work in the desktop app on macOS, the assistant reported that its commands ran in Linux, that /Users and /Volumes were unavailable, and that it could not access local files.

It requested local paths and further desktop steps without establishing a usable local-file mechanism, then advised that a local Codex session was required.

A separate local Codex session subsequently read original files on the Mac successfully.

Original session model and effort

• Model: Astra (reporter-confirmed; not independently recovered from task metadata).
• Reasoning effort: High (reporter-confirmed; not independently recovered from task metadata).

Evidence and limits

• The original Linux and missing-path results are assistant-reported. Their raw tool outputs have not been independently recovered.
• Successful local reads in the separate Codex session were directly verified.
• The original Work execution selection, account eligibility, and local-folder authorization have not been verified.
• This is not yet a reproducible, confirmed local Work defect.

Environment observed during follow-up: macOS 26.6.2, arm64; installed ChatGPT app version 26.901.51231, build 8109. The original session’s app build is unconfirmed.

Expected behavior

The interface and assistant should clearly identify the execution environment and available local-file mechanisms before requesting local paths. If a session cannot access the computer, guidance should explain the supported local Work route and verify it before claiming access.

OpenAI documents a Work locally selector for tasks needing local files. Local Codex is therefore an alternative, not the only documented route. Official Work guide

Requested clarification

1. What identifies an existing Work conversation as local or cloud?
2. What is the supported route from a cloud-backed conversation to local Work?
3. How should users distinguish missing Work Local eligibility from a folder-permission problem?
4. Can assistant guidance explicitly check available mechanisms instead of treating the desktop interface or a pasted path as proof of access?

Proposed reproduction test — not yet performed

Start a fresh Work conversation with Work locally selected. Open one authorized local folder. Attempt a read of an existing harmless file. Record the selected mode, available file mechanism, and exact result.

Disclosure

Personal paths, task identifiers, work topics, project names, and exact incident timing are omitted. No original transcript or screenshot is attached. Technical version information is retained for diagnosis. This report was prepared with AI assistance.

Start with the proposed reproduction using a fresh Work conversation, the Work locally selector, and an authorized folder; record the execution mode and exact file-access result. Read the linked Official Work guide and compare its documented route with the observed guidance. Done means the supported local/cloud paths, eligibility checks, and folder-permission distinction are clearly documented or reproducibly characterized.