AI Agent Hits Wall Attaching Files Despite Completing Every Other Form Field
A developer using an AI agent to fill out a web listing form found that while all text fields were completed successfully, the agent was unable to attach three PNG images. The Claude Code desktop app on Windows 11 provides a file_upload tool via the Claude in Chrome extension, but it restricts uploads to files explicitly shared within the session. Despite trying four different methods — including allowed directories, temp folders, and custom outputs and uploads subfolders — every attempt returned the same access error. The developer discovered that even files the agent had generated itself, seconds earlier, in a permitted directory could not be uploaded. The article concludes that all three documented workarounds for file sharing are effectively non-functional on this particular setup, leaving the file-attachment capability inaccessible.
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