Uploading more than two training files at once in Dashboard → Automations → Training Data is unreliable. Files fail very quickly and land in a Failed state, even for small files (for example a 1.8 KB Markdown file that reported 0 words).
Failed files then have to be removed one by one and re-uploaded, which makes seeding an agent with a real documentation set slow and error prone.
Requested behaviour
Multi-file selection should upload reliably, with queueing or throttling instead of parallel failures.
Show the actual reason a file failed (size, type, conversion error, rate limit) rather than a generic Failed label.
Offer a retry action on failed files instead of requiring manual delete and re-upload.
Reported by a customer evaluating Featurebase who is loading a Markdown documentation set into the AI agent.
