The first time I opened Cowork, my hand hovered over the "select a folder" button for longer than I'd like to admit. Picking my everyday working folder would have been the fastest path. It also held half-written drafts, client correspondence, and config files I couldn't fully account for.
Here's the short version: for the first week, hand over only folders you could lose without a bad night's sleep. Once I settled on that sentence, working with Cowork felt a lot calmer. Below are the three folders I handed over in order, and the one I never did.
What Cowork can actually touch
According to the official help article, Cowork can read and write only inside the folders you've connected. It also asks for your explicit permission before permanently deleting any file.
Those two facts are reassuring, and they're also the basis for a line to draw. Whatever sits in a connected folder is visible to Cowork, and with your approval it can be changed or removed. So choosing which folder to connect is the first and biggest safety control you have.
One more setting matters early: the approval mode (Manual, Auto, or Skip). For the first week, I'd stay on Manual or Auto. Skip is for folders whose contents you know completely.
Folder one: an empty practice folder
The first folder I connected was empty. I called it "cowork-practice." I wasn't testing results. I only wanted to see three things:
- Where my requested output lands, and under what name
- How often Cowork asks for permission along the way
- What the delete-permission prompt looks like in practice
If you're comfortable with a terminal on macOS, this takes seconds. A new folder made in Finder works just as well.
# What this solves: see how Cowork behaves without exposing real files
mkdir -p ~/cowork-practice
echo "A test note. Fine to lose." > ~/cowork-practice/memo.txt
ls -la ~/cowork-practice # look at the contents yourself before connectingThat last ls is a small habit worth keeping. Listing a folder before you hand it over prevents the "wait, that was in there?" feeling later.
Folder two: a copy of real files
Once the practice run felt familiar, I moved on to real material, but as a copy, never the original.
Think of a pile of receipt images or a batch of photos you've been meaning to sort. Put the copy inside the practice folder.
# What this solves: try sorting or data-entry requests while the original stays untouched
cp -R ~/Documents/receipts-2026-10 ~/cowork-practice/receipts-copy
# Why a copy: undoing a bad rename is harder than never exposing the originalAs an indie developer, I've spent years sorting screenshots and spreadsheets that pile up around app operations. File organization is one of the places Cowork shines, which is exactly why I'd test it on a copy first. If the result disappoints, delete the folder, rephrase the request, and try again.
Folder three: a place for finished work
The third folder receives finished output only. I named it "cowork-output."
Keeping working files and results apart means what Cowork made never gets mixed up with what's yours. You review the output, and if it's good, you move it into place yourself. Keeping that final step in human hands means I feel no extra worry as the scope grows.
The one I held back: credentials
I never connected the folder holding password notes, API keys, and service credentials.
The reason is simple: anything in a connected folder is readable by Cowork. Readable means there's a chance the contents surface in on-screen output or in logs during a task. I couldn't find any convenience worth that trade.
| Folder | When | Contents | What to check |
|---|---|---|---|
| Practice (empty) | Day one | A test note only | Output location, prompt frequency, delete screen |
| Copy of real files | A few days in | Duplicates of originals | Quality of sorting or transcription |
| Output folder | Same time | Starts empty | Whether results stay separate from your files |
| Credentials folder | Never | Passwords and keys | n/a |
When something goes wrong, check these first
The official troubleshooting section lists "files aren't appearing where expected." It points to two checks: whether you granted the right file access, and where Cowork said it would put the output.
Everyone has opened the wrong folder hunting for a result. Saying the output location out loud, once, resolves more of these than you'd expect.
Your next step
Make one empty folder today, connect only that, and ask Cowork to write one line of text into it. Seeing the permission prompt once changes how you feel about choosing the next folder.
I'd like to keep to this order myself, for a long while yet.