Claude Projects File Upload and Indexing Issues Documented

Core Issues with Claude Projects File Handling

Multiple users report persistent problems with Claude Projects' file upload and indexing system. The issues appear to be backend-related and affect functionality across browsers and projects.

The RAG Switching Problem

Claude Projects automatically switches from direct file loading to RAG (Retrieval-Augmented Generation) search mode at approximately 13 files, regardless of total file size or token count. One developer reported having 15 files totaling 73,000 tokens (only 35% of the 200K context window) still triggered search-only mode. The UI displays "To save space in chats, Claude will look up specific information as needed" at just 2% of project capacity.

Broken Indexing System

There's a confirmed bug where the system reports files as "fully indexed and ready" but search returns errors indicating the files aren't indexed at all. This creates a situation where uploaded files appear in the interface but remain unreadable by Claude.

Persistent Cache Issues

When files are deleted and re-uploaded — even with new filenames — Claude continues referencing the content of the original deleted files. The cache appears to be content-based rather than filename-based. Standard troubleshooting methods like new chat sessions, explicit instructions, and full re-uploads don't resolve the issue.

Workarounds and Reporting

The issues are cross-browser and cross-project, indicating they're backend problems at Anthropic. Users experiencing these problems should:

• Report the issue on support.anthropic.com
• Reference GitHub issue number #25759 in reports
• Submit tickets to increase visibility of the problem