Where the work actually happens
Most surprises in Cowork come from one thing: not knowing where the work is running. A few minutes here explains almost all of them.
By default a task runs in the cloud. Anthropic's documentation puts it plainly: the agent loop and the code run in an isolated, temporary sandbox on Anthropic-managed infrastructure, and each session gets its own, created when the session starts and destroyed when it ends.
So how does it read a file on your laptop
It asks your machine for it. When a cloud session needs something local, the request goes through the Claude Desktop app on that device over a connection Anthropic brokers, and it can only reach folders you have connected on the desktop.
Two consequences worth remembering. If the desktop app is closed, a cloud session cannot reach your local files, and if you connected only one folder, that is genuinely all it can see.
What the sandbox can reach on the network
Less than you might assume, and deliberately. All traffic leaving the sandbox passes through a proxy the sandbox cannot reconfigure or bypass, only allow-listed destinations are reachable, and it cannot reach private, internal, link-local or cloud-metadata addresses.
That is why a task cannot fetch something from your company intranet by itself. It is not a bug to work around, it is the boundary doing its job.
Connectors are handled elsewhere
When a task uses a connector, the tokens never enter the sandbox. Those calls are made on the server side. So a task that reads your calendar is not holding your calendar credentials, which is the property you want if anything it reads ever turns out to be hostile. Lesson 16 is about exactly that.
The local option
On the desktop there is a second mode where the agent loop runs on your own device and code execution happens in a virtual machine isolated from your operating system by the platform's hypervisor. Cloud is the default and the one to learn first, but knowing the other exists explains why some behaviour differs between machines.
- Open the desktop app and look at exactly which folders are connected. Most people have connected more than they remember.
- Ask a task to read something in a folder you have not connected, and read what it says.
Slow is fine. Stopping is the only problem.