Cowork's First Step, Folder Connect: Open a Drawer to AI

"Is it OK to trust my files to an AI?" Anyone gets this anxiety the first time they open Cowork (Cowork). But Cowork built this worry into its design from the start. It can see nothing except the folders you open yourself. So the first step of everything is "folder connect." It's like opening a drawer to your assistant and saying, "you may look in this one."

Definition

Folder connect is you directly designating which folder Cowork is allowed to work in. Cowork only reads files inside connected folders, and saves any new output inside them too. It can't see unconnected folders at all.

This is Cowork's most important first step. If you don't open a folder, Cowork can't start anything — no organizing, no document writing, nothing. Conversely, this means sensitive folders are safe as long as you simply don't connect them.

How to use it (by difficulty)

Basics — connecting a folder

Press the connect-folder (add-folder) button on the Cowork screen and a folder-selection window appears. Pick the folder to work in, click allow, and that's it. For example, for an Obsidian notes folder you'd pick a location like this.

C:\Users\username\Documents\Obsidian-doc

(On Mac it's in the form ~/Documents/Obsidian-doc.) Once connected, the folder name shows on the Cowork screen, and from now on Cowork can read files inside that folder and save new documents there too.

Applied — assigning work to the connected folder

organize this folder

Work runs only within the connected folder. Since you've opened the folder, you can freely assign tasks like organizing, document writing, and searching inside it.

Advanced — connecting separate folders per task

connect the blog folder and the tax folder separately

When purposes differ — like blog work and tax work — connect the folders separately. Then work doesn't get mixed up, and one task never touches another folder's files.

Common pitfall — "why does it say it can't see my files?"

If you tell Cowork "organize the photos on my desktop" but get back "cannot access that folder," you haven't connected that folder yet. This isn't a malfunction — it's intended security behavior. Cowork never peeks into folders it wasn't permitted to. The fix is simple. Connect that folder first, then give the command again.

A real case

I once connected just one Obsidian notes folder and had Cowork create a "Claude command dictionary" inside it. Cowork read and referenced the existing notes in that folder, and saved the newly organized document in the same folder. Because it never touched any other folder, I could entrust it with peace of mind. (This very post you're reading was made that way too.)

Use it like this too

• It only sees connected folders: The basic principle for security. If you don't connect it, it can't see it.
• Output stays in that folder: Even after work ends, the files it made are preserved right there in the folder.
• Leave out sensitive folders: For sensitive folders like personal photos or financial records, simply don't connect them.
• Folders per task: Splitting and connecting folders by purpose — blog, tax, customer management — keeps things tidy.

Tip: At first, connect just one unimportant folder and test lightly. Once you're used to it, expand to work folders without any worry.

Wrap-up

The key is one sentence. Cowork starts working only once you open a folder — and it can never see folders you didn't open. This simple rule is what lets you use Cowork with peace of mind. Connect only the folders you need, and leave the sensitive ones out. That's the first step and the most reliable safeguard.

Based on: Claude Code v2.1.154 (2026.05)