Anthropic API: PDF Upload Exceeds 100-Page Limit and freezes all context / progress, even after exit

Bug Description

• Attempted to have the bot review a large PDF
• It tries, gets a 400 PDF Too Long
• I ask it to do something else, same error. Cant seem to clear it out.
• I attempt to compact, refuses with same error
• I exit and then resume the chat, same thing.
• I have to kill this chat to continue using.

⏺ Now let me check the reference book that was mentioned to see if it contains spell information:

⏺ Read(~/Code/ars-saga-manager-v2/docs/reference-books/arm5-grand-grimoire-of-hermetic-spells.pdf)
⎿ Read PDF (3.6MB)
⎿ API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLJCsyisXTqRiCuhX51C"}

cont

⎿ API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLJHK7RwRtAypikTUYVS"}

ok That doesn't seem to work because it's a really big PDF. So look through that repo, because I'm pretty sure at one point I had a.md file with all of the instructions.If that doesn't work, can you run Gemini

CLI, which I have installed here, and use it to grep through for you. It doesn't have a limit.
⎿ API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLKBJKznx82iBLZjCKw4"}

Yeah, I know. Stop trying to actually read the PDF.

⎿ API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLKFoCgaNB6qxQfkdNeC"}

/compact

⎿ Error: Error during compaction: Error: API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLKUwFjbiy2EBXwKqvpg"}

/exit

⎿ (no content)

hello are you there

⎿ API Error: 400 {"type":"error","error":{"type":"invalid_request_error","message":"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be
provided."},"request_id":"req_011CSLKdchXAhfkZeditQsf5"}

Environment Info

• Platform: darwin
• Terminal: cursor
• Version: 1.0.86
• Feedback ID:

Errors

[{"error":"Error: 400 {\"type\":\"error\",\"error\":{\"type\":\"invalid_request_error\",\"message\":\"messages.38.content.0.pdf.source.base64.data: A maximum of 100 PDF pages may be provided.\"},\"request_id\":\"req_011CSLKdchXAhfkZeditQsf5\"}\n    at b4.generate (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:932:2412)\n    at dP.makeStatusError (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:949:2101)\n    at dP.makeRequest (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:949:5315)\n    at process.processTicksAndRejections (node:internal/process/task_queues:95:5)\n    at async LD1.showErrors (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:27238)\n    at async LD1 (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:16345)\n    at async l9B (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:27089)\n    at async file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:22183\n    at async dH0 (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:3514)\n    at async V11 (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:1904:22153)","timestamp":"2025-08-21T05:43:11.501Z"},{"error":"AxiosError: Request failed with status code 403\n    at UN (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:692:1077)\n    at Unzip.V0 (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:693:9955)\n    at Unzip.emit (node:events:536:35)\n    at Unzip.emit (node:domain:489:12)\n    at endReadableNT (node:internal/streams/readable:1698:12)\n    at process.processTicksAndRejections (node:internal/process/task_queues:82:21)\n    at G91.request (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:695:2088)\n    at process.processTicksAndRejections (node:internal/process/task_queues:95:5)\n    at async CW8 (file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:2419:470)\n    at async Promise.all (index 0)\n    at async file:///Users/alexanderhuth/.nvm/versions/node/v20.19.3/lib/node_modules/@anthropic-ai/claude-code/cli.js:2405:9163","time

Note: Error logs were truncated.