Image Upload Exceeds 5 MB Size Limit in API Request

[NerdNestFelix]

Bug Description
i keep getting this for anything I type API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.
0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880
bytes"}}

Environment Info

• Platform: darwin
• Terminal: WarpTerminal
• Version: 1.0.24
• Feedback ID: 179665c7-616b-4a83-b1d2-80438c4658d9

Errors

i keep getting this for anything I type API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.
    0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 
    bytes"}}

**Environment Info**
- Platform: darwin
- Terminal: WarpTerminal
- Version: 1.0.24
- Feedback ID: 179665c7-616b-4a83-b1d2-80438c4658d9

**Errors**
```json
[{"error":"Error: Command failed: security find-generic-password -a $USER -w -s \"Claude Code\"\nsecurity: SecKeychainSearchCopyNext: The specified item could not be found in the keychain.\n\n    at genericNodeError (node:internal/errors:983:15)\n    at wrappedFn (node:internal/errors:537:14)\n    at checkExecSyncError (node:child_process:882:11)\n    at execSync (node:child_process:954:15)\n    at HZ (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:659:3921)\n    at file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:8863\n    at Q (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:526:17199)\n    at tJ (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:8009)\n    at HS (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:7090)\n    at T6 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:11202)","timestamp":"2025-06-15T06:25:07.968Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes\"}}\n    at h6.generate (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1329:12578)\n    at Lw.makeStatusError (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:2082)\n    at Lw.makeRequest (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:5257)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async ME2.K11.showErrors (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:22008)\n    at async K11 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:12203)\n    at async ME2 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:21854)\n    at async file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17103\n    at async yt1 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:5151)\n    at async Fu (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17073)","timestamp":"2025-06-15T06:26:10.388Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes\"}}\n    at h6.generate (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1329:12578)\n    at Lw.makeStatusError (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:2082)\n    at Lw.makeRequest (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:5257)\n    at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n    at async ME2.K11.showErrors (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:22008)\n    at async K11 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:12203)\n    at async ME2 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:21854)\n    at async file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17103\n    at async yt1 (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:5151)\n    at async Fu (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17073)","timestamp":"2025-06-15T06:26:18.797Z"},{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes\"}}\n    at h6.generate (file:///Users/<my-user>/.nvm/versions/node/v22.12.0/lib/

Note: Error logs were truncated.

[{"error":"Error: Command failed: security find-generic-password -a $USER -w -s "Claude Code"\nsecurity: SecKeychainSearchCopyNext: The specified item could not be found in the keychain.\n\n at genericNodeError (node:internal/errors:983:15)\n at wrappedFn (node:internal/errors:537:14)\n at checkExecSyncError (node:child_process:882:11)\n at execSync (node:child_process:954:15)\n at HZ (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:659:3921)\n at file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:8863\n at Q (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:526:17199)\n at tJ (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:8009)\n at HS (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:7090)\n at T6 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:582:11202)","timestamp":"2025-06-15T06:25:07.968Z"},{"error":"Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes"}}\n at h6.generate (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1329:12578)\n at Lw.makeStatusError (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:2082)\n at Lw.makeRequest (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:5257)\n at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n at async ME2.K11.showErrors (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:22008)\n at async K11 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:12203)\n at async ME2 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:21854)\n at async file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17103\n at async yt1 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:5151)\n at async Fu (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17073)","timestamp":"2025-06-15T06:26:10.388Z"},{"error":"Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes"}}\n at h6.generate (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1329:12578)\n at Lw.makeStatusError (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:2082)\n at Lw.makeRequest (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1344:5257)\n at process.processTicksAndRejections (node:internal/process/task_queues:105:5)\n at async ME2.K11.showErrors (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:22008)\n at async K11 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:12203)\n at async ME2 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:21854)\n at async file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17103\n at async yt1 (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:5151)\n at async Fu (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/node_modules/@anthropic-ai/claude-code/cli.js:1698:17073)","timestamp":"2025-06-15T06:26:18.797Z"},{"error":"Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.0.content.1.image.source.base64: image exceeds 5 MB maximum: 5607404 bytes > 5242880 bytes"}}\n at h6.generate (file:///Users/felixflores/.nvm/versions/node/v22.12.0/lib/

**Note:** Error logs were truncated.

[ARanch]

also getting this. I originally started in [session 1] with inputting an image that was too large.

I then scaled the image below the 5 mb and 8000 px requirement, but i kept getting the same error om [session 1].
then tried renaming the file, but still got the same error [session 1].
then spawned [session 2] fresh, and in this session it worked.

[stevysmith]

If you tap "esc" twice you can go back to a previous message before this happened and fork the conversation from there so you can continue

[mendelgordon]

Same issue here

[evolsb]

Additional Finding: Clipboard Caching Bug

I'm experiencing a related but distinct behavior that suggests a clipboard caching issue:

Symptoms

• Pasting a screenshot from CleanShot triggers 5MB error: image exceeds 5 MB maximum: 5290848 bytes > 5242880 bytes
• Every subsequent paste triggers the same error, even with different/smaller screenshots
• Restarting Claude Code temporarily fixes the issue (one successful paste, then error returns)

Key Observation

The same 5MB error occurs regardless of the actual size of newly pasted images, suggesting Claude Code is:

1. Caching the first large image in memory
2. Reusing cached clipboard data instead of reading fresh clipboard content
3. Only clearing the cache on restart

Reproduction Steps

1. Take a screenshot with CleanShot (generates ~5MB PNG on Retina display)
2. Paste into Claude Code → Get 5MB error
3. Take a different, smaller screenshot
4. Paste again → Same 5MB error (proving it's using cached data)
5. Restart Claude Code
6. Paste works once, then error repeats

Environment

• Platform: macOS (Darwin 24.6.0)
• Screenshot tool: CleanShot
• Display: Retina (generates 2x/3x resolution screenshots)
• Claude Code Version: Latest

Workaround

Configure CleanShot to export JPEG at 80-90% quality instead of PNG to stay under 5MB limit.

Impact

This makes the existing 5MB issue worse because once triggered, the session is permanently broken for all image pastes, not just oversized ones. The cache should either:

• Not exist (always read fresh from clipboard)
• Clear after each paste
• Automatically compress images before caching

[itinance]

BUMP on this. Once this happens, there is no way back to normal any more. You can add more messages in the chat without any image and it will stick with this error. You need to restart the claude cli

[stevysmith]

BUMP on this. Once this happens, there is no way back to normal any more. You can add more messages in the chat without any image and it will stick with this error. You need to restart the claude cli

This helps in existing chats #2104 (comment)

[github-actions]

This issue has been inactive for 30 days. If the issue is still occurring, please comment to let us know. Otherwise, this issue will be automatically closed in 30 days for housekeeping purposes.