[Bug][ChatGPT Classic][macOS] Pasting an image freezes one conversation and makes it persistently unopenable

What version of the Codex App are you using (From “About Codex” dialog)?

ChatGPT Classic 1.2026.184 (1784145287)

What subscription do you have?

ChatGPT Pro

What platform is your computer?

Darwin 25.5.0 arm64 arm (macOS 26.5.2 build 25F84, Apple Silicon)

What issue are you seeing?

This report concerns the separate legacy ChatGPT Classic macOS app (/Applications/ChatGPT Classic.app, bundle identifier com.openai.chat). It is not about the new unified /Applications/ChatGPT.app (com.openai.codex), and it is not a Codex task.

Pasting a normal screenshot from the macOS clipboard into the composer of one existing conversation caused ChatGPT Classic to become unresponsive and display the macOS beachball. No recoverable upload error was shown.

After force-quitting and relaunching ChatGPT Classic, opening that same conversation repeatedly makes the app unresponsive again. Other conversations in ChatGPT Classic still open normally. The exact same affected conversation opens normally on chatgpt.com in Chrome, including its latest messages. This isolates the failure to ChatGPT Classic, possibly its local image-draft/upload restoration or conversation-rendering path.

What steps can reproduce the bug?

1. Launch /Applications/ChatGPT Classic.app.
2. Open an existing ChatGPT conversation.
3. Copy a normal screenshot to the macOS clipboard.
4. Paste the screenshot into the conversation composer.
5. Observe that ChatGPT Classic becomes unresponsive and macOS displays the beachball.
6. Force quit and relaunch ChatGPT Classic.
7. Select the same conversation again.
8. Observe that the app becomes unresponsive again before the conversation becomes usable.
9. Open another conversation in ChatGPT Classic and observe that it works normally.
10. Open the exact affected conversation on chatgpt.com in Chrome and observe that it loads normally.

No public session/conversation ID is included because the conversation contains private account-support correspondence. I can provide it through a private OpenAI channel if requested.

What is the expected behavior?

The screenshot should be attached to the draft, or the app should show a recoverable upload error. A failed paste/upload must not freeze the entire app or make that conversation persistently unopenable after relaunch.

Additional information

Exact affected application:

• Path: /Applications/ChatGPT Classic.app
• Bundle identifier: com.openai.chat
• Version: 1.2026.184
• Build: 1784145287

The separately installed new unified app is /Applications/ChatGPT.app, bundle com.openai.codex, version 26.820.60940, build 7119. It is not the affected product surface.

Process observations after the incident:

• ChatGPT Classic remained alive rather than crashing.
• Physical footprint was approximately 1.5 GB and RSS approximately 1.29 GB around 10 minutes after launch.
• A post-incident process sample showed the AppKit main thread back in its normal event loop, so the stall may be transient or occur in draft restoration/content rendering rather than remain as a permanent main-thread deadlock.
• No recent ChatGPT Classic crash/hang report was found in ~/Library/Logs/DiagnosticReports.
• No relevant recent Classic error/fault entry was found in the macOS unified log query.

Sanitized conversation characteristics:

• Existing web-origin ChatGPT conversation
• More than 10 turns
• Multiple prior PNG/JPEG attachments
• Several long pasted messages, Markdown, block quotes, and older :::writing structured blocks
• Recent turns completed with no observed turn errors
• Same conversation currently works on chatgpt.com

The screenshot is not attached because it shows the account name, conversation URL, and private correspondence. The conversation title, raw messages, complaint identifiers, access codes, and conversation ID are intentionally omitted.

Related but different: #37580 concerns individual conversations getting stuck inside the Chat surface of the new unified app. This report concerns the separate ChatGPT Classic app and has a specific image-paste trigger followed by persistent failure when reopening that conversation.

Another related but different report is #33988. That issue concerns the new unified Codex app and an image placeholder that spins indefinitely after sending. The present report concerns the separate ChatGPT Classic app, a macOS beachball during paste, and the affected conversation remaining persistently unopenable in Classic after relaunch.

Start by reproducing the paste flow in /Applications/ChatGPT Classic.app, using the existing conversation and macOS screenshot clipboard described in the report. Compare behavior when reopening that conversation in Classic with the same conversation in Chrome, and inspect the composer paste, draft or upload restoration, and conversation-rendering entry points. Done means a pasted screenshot either attaches or produces a recoverable error without freezing the app or making the conversation unopenable.