WorkBuddy Can Write Lesson Plans but Fails to Read Essays in My Folder?

I've always had a counter-intuitive feeling: the most annoying thing about AI tools is often that they seem to agree to do something, but then can't find the stuff I placed somewhere.

I've been using WorkBuddy for a short time. Usually, I just ask it to organize spreadsheets or generate comment frameworks sporadically. These past two days, I wanted to aggregate essay drafts submitted by my class on Thursday. Following the beginner tutorial, I created an "Essay Review Workspace," uploaded several PDFs and Word docs into the task, and tried to use Craft to extract evidence by paragraph. Instead, it replied with something like "Local folder access permission denied," and the artifact area on the right only generated an empty document. Clicking download yielded no content.

I'm not sure if I set it up wrong. I tried creating a new task, uploading only a single Word doc, and telling it not to touch local files. I also went into settings to look for folder authorization, but it seems I can only check boxes for Desktop, Documents, etc., and I don't dare give it access to all my computer data. The tutorial says different task contexts are independent, so I guess maybe I didn't select the workspace correctly, or perhaps dragging everything in bulk before stating requirements was fundamentally inappropriate.

It's also possible I'm treating it too much like a chat tool. When using DeepSeek or Kimi, I got used to pasting text into the chat box. Now that WorkBuddy wants to process files, I really haven't mastered the local permission step. Could it be that the free version doesn't support multi-file batches, or do I need to install a Document Processing Skill first?

Has any teacher or student encountered situations where WorkBuddy says it can't find files or the artifact area is empty? Is it generally an authorization issue, or is the task context not established properly?