Image Upload Exceeds Size Limit Causing Persistent API Request Failure

[alessandrobologna]

Bug Description
after submitting an image too large, the context is polluted and any other request returns the error API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.17.content.1.image.source.base64.data: At least one of the image dimensions exceed max allowed size for many-image requests: 2000 pixels"}}

Environment Info

• Platform: darwin
• Terminal: cursor
• Version: 1.0.41
• Feedback ID: 635919c9-d04d-4562-9842-2a0a15d8e011

Errors

[{"error":"Error: Command failed: security find-generic-password -a $USER -w -s \"Claude Code\"\nsecurity: SecKeychainSearchCopyNext: The specified item could not be found in the keychain.\n\n    at genericNodeError (node:internal/errors:983:15)\n    at wrappedFn (node:internal/errors:537:14)\n    at checkExecSyncError (node:child_process:882:11)\n    at execSync (node:child_process:954:15)\n    at JI (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:702:3921)\n    at file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:9038\n    at Q (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:526:13327)\n    at _X (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:8184)\n    at w_ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:7265)\n    at U9 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:623:11432)","timestamp":"2025-07-03T16:45:23.855Z"},{"error":"Error: Tool mcp__puppeteer__puppeteer_click not found\n    at dT2 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1958:5596)\n    at ZU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:19802)\n    at UP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:42556)\n    at wP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38105)\n    at o$ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38033)\n    at MU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:37887)\n    at EJ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:34977)\n    at f5 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:4822)\n    at DB (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:32233)\n    at A.Q.updateContainer (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:71:1835)","timestamp":"2025-07-03T16:45:27.222Z"},{"error":"Error: Tool mcp__puppeteer__puppeteer_click not found\n    at dT2 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1958:5596)\n    at ZU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:19802)\n    at UP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:42556)\n    at wP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38105)\n    at o$ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38033)\n    at MU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:37887)\n    at EJ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:34977)\n    at f5 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:4822)\n    at DB (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:32233)\n    at A.Q.updateContainer (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:71:1835)","timestamp":"2025-07-03T16:45:27.236Z"},{"error":"Error: Tool mcp__puppeteer__puppeteer_screenshot not found\n    at dT2 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:1958:5596)\n    at ZU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:19802)\n    at UP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:42556)\n    at wP (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38105)\n    at o$ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:38033)\n    at MU (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:37887)\n    at EJ (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:34977)\n    at f5 (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:65:4822)\n    at DB (file:///Users/alessandro/.claude/local/node_modules/@anthropic-ai/claude-code/cli.js:67:32233)\n    at A.Q.updateContainer (file:///Users

Note: Error logs were truncated.

[baryon]

I didn’t upload any images and still encountered this issue—I only asked CC to modify the copy on the webpage and didn’t upload any images to him. After this error appeared, even the /compact command started returning the same error.

/compact 
  ⎿ Error: Error during compaction: Error: API Error: 400 {"type":"error","error":{"type":"
    invalid_request_error","message":"messages.95.content.12.image.source.base64.data: At 
    least one of the image dimensions exceed max allowed size: 8000 
    pixels"},"request_id":"req_********************"}

[gthb]

Found my session afflicted with this same thing soon (within a day) after I started working with the chrome-devtools MCP server. That was going great until the session was entirely incapacitated by this error. And yep, /compact is failing too in this session — presumably because it's trying to read that same poisoned item in the context. I'll hazard a guess that a screenshot of the remote-controlled Chrome window (or of a canvas that I have in there in a scrollable container) landed in the context despite violating some size-limit invariant, and then there's no coming back from that.

[saynth-ai]

Error: Error during compaction: Error: API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.380.content.0.image.source.base64.data: At least one of
the image dimensions exceed max allowed size: 8000 pixels"},"request_id":"req_011CU35RmzHC6WGfCL6kKbKB"}

[lukasmalkmus]

Same here! Would be nice to have a command to remove the bad message from the context to compact or instruct otherwise.

[JimSander-uniphore]

My Experience: 12+ Hours of Work Lost

I encountered this exact issue and lost over 12 hours of productive working history with Claude Code. The session became completely unrecoverable after an image >8000 pixels was added to the context.

Impact:

• All subsequent requests returned the same API 400 error
• No way to remove or compact the problematic message
• Had to abandon the entire session and lose all conversation history
• Now extremely hesitant to use images in any Claude Code session due to this risk

Critical Need: This needs a recovery mechanism urgently. Suggestions:

• Pre-validate image dimensions before adding to context
• Provide a command to remove specific messages from context (like /remove-message <index>)
• Make /compact resilient to skip/remove invalid messages instead of failing
• Add a /recover command to sanitize corrupted contexts

This is a severe UX issue that makes the tool feel fragile when working with visual content, especially when using MCP servers that generate screenshots automatically.

---

Meta note: This comment was drafted by Claude Code itself—the very tool that caused the problem. Even the offender agrees this needs fixing! 😅

[tokmakoff]

/rewind worked for me as a recovery mechanism. I went back in the context stack however-many prompts to before the bad image from Chrome was added.

[JoeEarly]

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.8.content.5.image.source.base64.data: At least one of the image dimensions exceed max allowed size: 8000 pixels"},"request_id":"req_011CVFsFR3Yo8qKa9SEVzj8F"}

Has any of the dev team looked at this?

[vovanrew]

Same issue to be

    image dimensions exceed max allowed size: 8000 pixels"},"request_id":"req_011CVFv8L4ojR1WvfaonMrw1"}```

[JoeEarly]

Same issue to be

    image dimensions exceed max allowed size: 8000 pixels"},"request_id":"req_011CVFv8L4ojR1WvfaonMrw1"}```

Well thanks for stating the obvious fella, my query was more in relation to has anyone looked at this from a dev POV with the view to fixing the ability to recover cleanly

[Keeline]

This is a vexing problem and I have been burned by it many times. Yesterday I decided to take a new approach. I use Claude Code on a MacBook Pro with Sequoia. I asked it to write a Bash script to check the pixel and byte sizes to ensure they are within the limits for any image view. If it is too large, it should use ImageMagick to resize or make a copy with the appropriate specs.

I further instructed it to add it to CLAUDE.md as a priority rule to use the script every time an image might be read into the session.

I decided to add some other instructions such as a mandate of using shellcheck on Bash scripts and lint for PHP and Python before they try to run them. I was also tired of nonsensical time references to I required the session to check the current date-time before making a statement.

I can provide the code for image screening (check_image_previe.sh). It is 154 lines with comments.

In the CLAUDE.md below I have added backslashes before the triple-backticks for the formatting in github. But they may cause a problem if left in for use. With the right prompt, this would be generated by Claude Code. But it shows the intent.

Having worked with Claude Code since May 2025, this is hopefully going to rein in some of the most frequent issues I have with it. Something akin to this should be part of the core system. Creating a fatal error loop that can't be resolved without starting a new session is a serious blocker for professional use of an otherwise good system.

James D. Keeline

# Claude Code Instructions

## Image Preview Safety
**CRITICAL:** Always use `./check_image_preview.sh <image_file>` before reading any image with the Read tool. This prevents Claude Code from attempting to load oversized images that cause infinite error loops and context loss.

### Image Constraints
- Maximum file size: 5MB
- Maximum dimensions: 2000px width OR height
- Script automatically checks both constraints
- Use `--fix` flag to auto-create compliant versions

### Example Usage
\```bash
# Check image before viewing
./check_image_preview.sh "/path/to/image.jpg"

# Auto-fix oversized images
./check_image_preview.sh --fix "/path/to/image.png"

# If it passes, then safe to use:
# Read "/path/to/image.jpg"
\```

This workflow prevents system crashes and preserves work context.

## Script Development Standards

### Bash Scripts
Always run shellcheck before finalizing any bash script:
\```bash
/opt/homebrew/bin/shellcheck script_name.sh
\```
Fix all warnings and errors. Common issues:
- Quote variables to prevent word splitting: `"$var"`
- Declare and assign separately: `local var; var=$(command)`
- Remove unused variables

### PHP Scripts
Check syntax before execution:
\```bash
php -l script_name.php
\```

### Python Scripts
Use appropriate syntax checkers:
- `python -m py_compile script.py` (built-in)
- `flake8 script.py` (if installed)
- `pylint script.py` (if installed)

**Always lint scripts during development to catch errors early.**

## Temporal References

**CRITICAL:** Always run `date` command before making any date/time-based statements or assumptions in conversations.

\```bash
date
\```

Current session time reference: Sat Nov 22 22:13:24 PST 2025

This ensures accuracy when discussing:
- File timestamps and modifications
- Log analysis and debugging
- Scheduling or time-sensitive operations
- Historical context of changes%

[jhilgert]

Hey everyone,

ran into the same problem that an oversized image corrupted my conversation with Claude Code. Since it had been running for 1 hour before - without any additional message from me - I was not able to simply rewind. Thus, I looked into the directory, which stores the conversation files (simple .jsonl files) and then basically asked Claude to fix itself. Here is its solution, which worked like a charm. Hope this helps some people until a proper fix is out:

Fixing Claude Code Conversation Stuck on Oversized Image

The Problem

When Claude Code tries to read an image larger than 5MB, the API rejects it with an error like:

API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.16.content.2.tool_result.content.0.image.source.base64: image exceeds 5 MB maximum: 6521204 bytes > 5242880 bytes"}}

The base64 image data is already saved in the conversation history (.jsonl file), so every subsequent message keeps sending the same oversized image, causing a loop of API errors. Even new messages won't work.

The Solution

1. Find the conversation file

Conversation files are stored in ~/.claude/projects/<project-path>/ with UUID-style names:

ls -la ~/.claude/projects/*/
# Look for files like: e45adf17-b504-4108-87f3-53c5eff292da.jsonl

2. Identify the problematic lines

Find which lines are huge (contain base64 image data):

awk '{print NR, length($0)}' <file>.jsonl | sort -k2 -n -r | head -10

Lines with millions of bytes are the culprits (normal lines are a few KB at most).

3. Create a backup

cp <file>.jsonl <file>.jsonl.backup

4. Fix with this Python script

import json

file_path = "<your-file>.jsonl"
problem_lines = [84, 85, 86]  # 1-indexed line numbers from step 2

with open(file_path, 'r') as f:
    lines = f.readlines()

for line_num in problem_lines:
    idx = line_num - 1  # Convert to 0-indexed
    data = json.loads(lines[idx])

    # Get tool_use_id and replace image content with text
    tool_use_id = data['message']['content'][0]['tool_use_id']
    data['message']['content'] = [{
        "tool_use_id": tool_use_id,
        "type": "tool_result",
        "content": "[Image removed - exceeded 5MB limit]"
    }]

    # IMPORTANT: Remove toolUseResult entirely (causes render crash if malformed)
    if 'toolUseResult' in data:
        del data['toolUseResult']

    lines[idx] = json.dumps(data) + '\n'

with open(file_path, 'w') as f:
    f.writelines(lines)

print("Fixed!")

5. Restart Claude Code

The conversation should now load without errors.

Key Points

• The fix replaces base64 image data with a text placeholder
• Must delete toolUseResult key entirely (not just modify it) - otherwise Claude Code crashes trying to render it with Cannot destructure property 'numLines' from null
• Keep the tool_use_id to maintain conversation continuity
• Original file size drops dramatically (e.g., 51MB -> 262KB)

Prevention

Before reading large images, resize them first:

# Resize to max 2000px width, quality 80%
convert large-image.jpg -resize 2000x -quality 80 smaller-image.jpg

# Or use ImageMagick to check size first
identify -format "%b" image.jpg