You actually did a solid job narrowing this down. From everything you tested, it really looks like a backend KB ingestion or validation issue rather than anything wrong with your Twilio, voice, or assistant setup. The fact that clean assistants work until files are enabled is a pretty strong indicator. I’d be happy to help you troubleshoot it further, are you creating/updating the assistants purely from the dashboard, or is there any API call involved when attaching the knowledge base files?
@Shabba