Does a cloud task upload my entire folder?
No. The documentation says your folders stay on your computer and Claude reaches only the folders you have connected. When a task needs a file, it fetches a copy of that file, not the whole folder. So exposure depends on which files the task actually uses, not on how large the connected folder is.
Why does the desktop app need to stay open?
By the documented design, your folders stay on your computer and a cloud session obtains files through the desktop app running there. The documentation does not explain the technical detail, but it is reasonable to infer that the desktop app is the bridge between the cloud and your local files. With the bridge gone, the session still runs but cannot reach files. That is inference, not an official architecture statement.
What are the steps to move an existing Cowork task to Claude Code?
Per the documentation: open the task, choose "Download task data," unzip the download, open the unzipped folder in Claude Code in the desktop app, then run /port-task-data. After that the task data lives in your local Claude Code environment. For a separate full backup, use "Export your Cowork data" on the desktop home card.
What practical effect does this have on how I schedule my day-to-day tasks?
Most directly, after handing off a task that needs local files, do not rush to close the desktop app; otherwise the task continues in the cloud but cannot read the files. Next, evaluate work involving sensitive files separately, and use Claude Code if needed. Finally, keep an Export backup of important tasks and confirm work and home do not share one account.
After October 6, new Pro and Max tasks run in the cloud by default. Two practical questions follow immediately: how does a cloud task reach a file on my computer, and if I do not want certain work leaving my machine, what exactly do I do? The official documentation answers both.
The documentation says your folders stay on your computer. Claude reaches only the folders you have connected, and only while the desktop app is open. When a cloud task needs a file, Claude fetches a copy of that file. When you delete the session, the fetched copies are deleted too under the data retention practices.
Per the documentation, if the app is closed the session itself keeps running but can no longer reach local files. In practice that suggests a trap: you hand off a task, close the laptop and quit the app, and the task carries on in the cloud but cannot produce what you expected because it cannot read your files. That scenario is my inference from the documented behavior, not an officially listed pitfall.
Local files, local connectors and local MCP servers, browser use and computer use all still need the desktop app. Reading the current tab through the Chrome side panel does not.
The documentation offers two routes. For a new task that should stay entirely on your computer, use Claude Code in the desktop app, which keeps your folders and history local. For an existing Cowork task: open it, choose "Download task data," unzip the download, open the unzipped folder in Claude Code, and run /port-task-data. To keep a copy of everything, choose "Export your Cowork data" on the desktop home card.
Do a simple triage. Tasks using ordinary files can stay in the cloud, as long as the desktop app is open when they need it. Tasks with sensitive files deserve evaluation for the Claude Code route. For important existing tasks, export a copy now. Also note the documentation says that separating work and home use requires separate accounts, since shared logins are not supported.