Setup and First Run

Enough theory. Let’s get Cowork running on your machine.

The whole setup takes under 5 minutes. By the end of this lesson, you’ll have completed your first Cowork task — and you’ll understand exactly how the safety controls work so nothing goes sideways.

Step 1: Get Claude Desktop

If you already have the Claude Desktop app installed, make sure it’s updated to the latest version. Cowork gets new features regularly, and older versions might not have everything we’ll cover.

Don’t have it yet? Download it from claude.ai/download. It’s available for macOS and Windows.

Install it like any other app. Sign in with your Claude account. You’ll need a paid plan — Pro ($20/month) at minimum.

✅ Quick Check: Which Claude plans include Cowork access? (Pro, Max, Team, and Enterprise — the Free plan doesn’t include it.)

Step 2: Switch to Cowork Mode

Once you’re in the Claude Desktop app, look at the top of the screen. You’ll see a mode selector with two tabs: Chat and Cowork.

Click Cowork. The interface changes — instead of a chat window, you’ll see a task-focused layout. The label might say “Tasks” depending on your version.

That’s it. You’re in Cowork mode.

Step 3: Grant Folder Access

Before Cowork can work with your files, you need to tell it which folder to use. Click “Work in a folder” and pick a directory.

Important: Start with something safe. Don’t point it at your entire Documents folder on day one. Good starting choices:

A Downloads folder you don’t mind reorganizing
A new folder you create specifically for testing (e.g., ~/CoworkTest)
A project folder with files you want organized

Why start small? Remember the Reddit user whose Cowork deleted 11GB of files after being told to “clean up”? That happened because they gave broad access and vague instructions. We’ll avoid both mistakes.

Step 4: Run Your First Task

Type a simple, specific task. Here’s one that works great as a first run:

Look through this folder and give me a summary of what's in it.
List the file types, how many of each, and the total size.
Don't change anything — just report.

Notice three things about this prompt:

Specific scope — “this folder” (not “my computer”)
Clear deliverable — “list the file types, how many, and total size”
Safety constraint — “don’t change anything”

Hit enter. Cowork will plan its approach, show you the steps, and ask if you want to proceed. Review the plan, approve it, and watch it work.

Your first task should complete in under a minute. You’ll get a clean summary of your folder contents.

Understanding Approval Gates

This is the safety feature that matters most. Cowork uses approval gates — checkpoints where it pauses and asks you to confirm before doing anything potentially destructive.

Actions that trigger approval gates:

Deleting files
Modifying important documents
Running scripts or commands
Accessing new folders beyond what you initially granted

Actions that don’t require approval:

Reading files
Creating new files
Generating summaries or reports

Think of it like a new employee asking, “Hey, I’m about to delete these 50 duplicate files — cool with you?” You can approve, modify, or cancel.

Try This: A Real Task

Now that you’ve got the basics, try something practical. Pick one of these:

For a messy Downloads folder:

Sort the files in this folder into subfolders by file type:
- PDFs → Documents/
- Images (jpg, png) → Images/
- Spreadsheets (xlsx, csv) → Data/
Leave anything you're unsure about in an "Unsorted" folder.
Show me what you did when you're done.

For a folder of meeting notes:

Read all the text files in this folder.
Create a single "meeting-summary.md" with:
- Date of each meeting (from the filename or content)
- Key decisions made
- Action items with who's responsible
Sort by date, most recent first.

For scattered receipts:

Go through the PDFs in this folder.
For each receipt, extract: date, vendor, amount, and category (food, transport, office supplies, etc).
Create a spreadsheet called "expense-report.csv" with these columns.

Pick whichever matches your actual files. That’s the whole point — Cowork works on your stuff.

What to Do When Things Go Wrong

Your first few tasks might not be perfect. That’s normal. Common early issues:

“I need access to…” — Cowork will tell you if it needs a folder it can’t reach. Just grant access to the specific folder it needs.

Incomplete results — If the output is missing something, just follow up: “You missed the PDF files in the subfolder. Can you include those too?” It keeps context within the session.

Unexpected changes — If something looks wrong, you can undo. Cowork doesn’t permanently destroy files without approval gates. But check immediately rather than hours later.

Usage limits — If you’re on the Pro plan, you might hit message limits during long tasks. Cowork uses more tokens than regular chat. If this happens often, the Max plan gives you 5x-20x the capacity.

Key Takeaways

Download Claude Desktop, sign in, click the Cowork tab — you’re in
Start with a safe, contained folder (not your entire drive)
Write specific tasks with clear deliverables and safety constraints
Approval gates protect you from destructive actions — review them carefully
Follow up in the same session if results need tweaking

Up Next

You’ve got Cowork running. Next, we’ll explore the interface — the file browser, context window, keyboard shortcuts, and how to structure longer tasks that need multiple steps.