You set a job running in Claude Cowork, shut the laptop, and went to do something else. When you came back it had either stopped, or finished but produced nothing you can find, or told you it could not see the folder you were certain you had connected. Nothing was broken. You just ran into the one thing about Cowork that nobody explains properly, and once you know it, you can work around it in about a minute.
Here it is in one sentence. A cloud session can reach the files on your computer only while the desktop app is open on that computer. It is a small version of a bigger point: a tool that knows your business has to be able to reach it.
This matters because those files are where your business actually lives. If the tool cannot reach them, it is back to guessing.
Two places the work can happen
It helps to picture two separate rooms.
The first is your computer, where your actual files live: the spreadsheets, the quotes, the folder of client documents. The second is Anthropic's servers, where the thinking happens. A Cowork session runs in that second room, not on your machine, which is exactly why it can keep working after you walk away.
Your files never move into that second room. Instead the desktop app on your computer acts as a doorway, and only for the specific folders you have connected. The session asks the app for a file, the app checks it is a folder you approved, and passes it through.
Close the app and the doorway closes with it. The session carries on thinking perfectly happily. It simply has nothing to reach into any more. Anthropic's own documentation says the same. A remote session reaches connected folders only while the desktop app is open, only for folders you have connected, and only with the permissions you set.
Why it is built that way, and why that is good news
It reads like a limitation. It is actually the safer design, and worth understanding rather than resenting.
The alternative would be uploading your business to a server so it is always reachable. Instead your files stay where they are, on your machine, and access is brokered every time by an app you control, folder by folder. Nothing is sitting somewhere waiting to be reached. If you shut the laptop, the door is shut, full stop.
For anyone handling client documents, that is the arrangement you want. It just needs to be a decision you make on purpose rather than something you discover at the wrong moment.
Three rules that stop it catching you out
1. Decide up front whether this is a thinking job or a files job.
If you want Claude to work something out with you, draft something, argue a plan through, it needs nothing from your computer and you can run it from anywhere, including your phone. If the job touches your actual files, it belongs on the desktop with the app open. Sorting this at the start saves the whole problem.
2. For a files job, leave the machine awake with the app running.
That is the whole workaround. Not glamorous, but it is the reliable one. If you want to close the lid and walk away, the job needs to be one that does not touch local files at all.
3. If you want to work from anywhere, put the files where the cloud can reach them.
Connect a cloud storage service such as Google Drive, and keep the documents that jobs depend on in there rather than only on your desktop. Then a session running on the servers can reach them without your laptop being part of the chain. This is the fix worth making once, because it removes the constraint permanently rather than working around it every time.
Send the job with everything it needs
There is a habit that comes out of all this and it is worth adopting whatever you use.
If you are handing a job to a session that might run remotely, package it so it does not have to reach back into anything. Put the instructions, the reference documents and any files it needs together in one place, and point the session at that. A job that depends on quietly reaching a folder somewhere else on your machine is a job that will fail the first time you are not sitting in front of it.
I found this out the ordinary way, by having something fail while I was away from the desk, and it changed how I set jobs up. Self-contained work runs anywhere. Work that assumes it is on your laptop only runs on your laptop.
The other half people miss
Files and chats are different things, and they behave differently.
Anything a session produces needs to be saved to a folder or to your cloud storage. If the useful part is only in the conversation, it exists only in that conversation, and there is no way to hand it to another session later. Chat is not storage. When a job finishes, the question worth asking is where did it save that, not just what did it say.
The plain version
Cloud sessions are genuinely useful. They keep working while you get on with your day and you can start one from your phone. The single thing to hold in your head is that they cannot reach your computer unless your computer is awake and the app is open.
Sort out where your working files live, once, and the whole problem disappears.
Working that out is not how most people want to spend a week. That is the part I set up for founders: your business, your files and your regular jobs arranged so the tool can reach them, with everything drafted and waiting for you to check rather than sent on your behalf. If you would rather skip the working out, quietcontent.com.au has a short intake and I do the rest.