Two AI agents now share one name. Which one you can get, what each asks before it acts, and how to check what’s gone after it acts.

Claude Cowork is Anthropic’s AI agent for paid Claude plans; Copilot Cowork is Microsoft’s agent inside Microsoft 365. You describe a job, and each one works through it on your files and apps.

In February, Nick Davidov gave Claude Cowork a job that sounds harmless. His post on X tells it: “Asked Claude Cowork organize my wife’s desktop, it stated doing it, asked for a permission to delete temp office files, I granted it, and then it goes ‘ooops’.”

The folder it had deleted held “all of the photos my wife made on her camera for the last 15 years. All photos of kids, their illustrations, friends’ weddings, travel, everything.” They were not in the trash, and iCloud had already synced the change. Apple pointed him to an iCloud feature that keeps deleted files for 30 days, and he watched it load “tens of thousands of files”.

A permission box asking to delete temp office files, its Allow key lit gold, beside a panel of photos labelled 15 years of photos and stamped deleted.

His agent did ask before it deleted something. By his account, the one yes was for temporary files.

Both companies now say their agent asks before deleting your files (Microsoft, on personal accounts). This guide covers which Cowork you can get, what each asks before it acts, what happened to the photos, and a check that lists what’s gone after a job.

The short version: in the UK on a personal account, Claude Cowork is the one you can use. It needs a paid plan, from $17 a month on Anthropic’s annual pricing. Copilot Cowork’s personal preview is only in the US and Canada, where Claude Cowork is available too. Anthropic says Claude Cowork asks before permanently deleting files; on personal plans, by default, it reviews other steps for safety itself and carries on. Before you give it a folder you care about, give it a copy, and list the files before and after.

Two agents with one name

Anthropic says Claude Cowork “brings Claude Code’s agentic capabilities to knowledge work beyond coding” (Claude Help, Get started with Claude Cowork). The first example task on that page is the kind of job Davidov gave it: “Organize my Downloads folder by type and date.”

The work runs on Anthropic’s machines: “Cowork runs your tasks in the cloud. Claude’s work runs on Anthropic’s servers, in an isolated environment, and your sessions and files are saved to your Claude account.” On Pro, Max and Ultra, that includes new tasks you start in the desktop app. Team and Enterprise can also run tasks on your own computer.

When a task needs your own files, “Claude reaches your computer through the Claude Desktop app, and only for the folders you’ve connected” (Claude Help, Use Claude Cowork safely).

Microsoft describes its version in one line: “Cowork helps you get work done by completing complex, coordinated actions across your apps, files, and data” (Microsoft Learn, Copilot Cowork FAQ).

On a personal account it can create and edit Word, Excel, PowerPoint and PDF files, draft and send email, manage your calendar and your OneDrive files, and run prompts on a schedule (Microsoft Support, Get started with Cowork). It runs in the browser, in the Copilot desktop app and in the Copilot mobile app. For personal accounts it is a preview; “Cowork for work or school accounts is generally available”.

The two are closer than the names suggest. Microsoft says its Cowork “can use Anthropic Claude models as a subprocessor for most reasoning, drafting, and tool-using work.”

So the useful comparison is who sells it, what it can reach, and what it asks before it acts.

Claude Cowork and Copilot Cowork side by side: who makes each, the plans that include it, whether a UK personal account can get it, where it runs, and what it asks before acting.

Which Cowork can you get?

Claude Cowork

Anthropic’s help page is plain: “Cowork is available to paid Claude plans (Pro, Max, Ultra, Team, Enterprise) only.” There is no Cowork on the free plan.

Anthropic’s pricing page shows prices in dollars, before tax. Pro is $17 a month on an annual plan ($200 billed up front) or $20 billed monthly. Max is $100 a month and Ultra $200. A Team standard seat is $20 a month billed annually or $25 monthly.

The United Kingdom is on Anthropic’s list of supported countries and regions.

The desktop app runs on macOS, Windows and Linux (in beta), but working on your own files, browser or screen needs “The Claude Desktop app for macOS or Windows, open and connected.” A desktop tidy-up like Davidov’s needs that app open with the folder connected.

On the web and in the mobile apps, Cowork is on Pro, Max, Ultra and Team (in beta on Team), and on Enterprise when an owner turns it on. Long, multi-step jobs use more of your allowance than a quick question.

Copilot Cowork

Microsoft’s plan table for individual subscriptions lists Cowork, in preview, on Microsoft 365 Premium (“Limited usage”) and Microsoft 365 Pro (“Highest usage”), and as “Not available” on Personal and Family. Its footnote: “Currently only available in the US and Canada.”

Microsoft is moving Copilot Tasks into Cowork, and Personal and Family subscribers who used Tasks lose it in the move (Microsoft Support, Updates to Copilot and the Copilot app).

At work the route is different. You need “a Microsoft Copilot license, Cowork enabled in your Microsoft Copilot environment, and usage-based and Cowork billing enabled”, which is your IT team’s decision. Microsoft limits Cowork to the regions Anthropic supports, a list that includes the UK, because it uses Anthropic’s models: “Cowork isn’t an exception.”

So in the UK on a personal account, Claude Cowork is the one you can get; at work, ask IT.

What does each Cowork ask before it acts?

Claude Cowork: modes, and a default

Claude Help describes three modes “that control when Claude asks your permission before taking an action”. In the newer combined Claude app they appear as two settings, Auto and Manual.

Manually approve (Manual): “Claude pauses and asks for approval for actions. You review each request and choose Allow or Deny.”

Automatically approve (Auto): Claude “reviews each action for safety (such as checking for data exfiltration or prompt injection) and automatically blocks anything it determines to be unsafe.” For connector tools that write or delete, unless you’ve blocked them, Anthropic’s table says “Claude decides”. For “work with real consequences”, which Anthropic lists as money, messages sent as you and important files, its advice is to “stay close and review what Claude does”.

Skip all approvals: “Claude doesn’t pause to ask and nothing checks its actions automatically.”

On Pro, Max, Ultra and Team, new tasks start in Auto; on Enterprise they start in Manual (Claude Help, Use Claude Cowork on Team and Enterprise plans).

Deletion is where Auto still asks. Use Claude Cowork safely says “Claude always asks before permanently deleting files, in any mode”, and the newer combined-app page says it asks “by default”. You “will need to select ‘Allow’ before Claude is allowed to perform deletion tasks.”

Computer use is the other case to know. Claude asks before it uses each app, then “clicks, types, and navigates your screen directly, without the permission checks that gate other Cowork tools.”

Copilot Cowork: a list of actions that ask

On personal accounts, “Before Cowork takes certain actions, including writing files, it asks for your permission” (Microsoft Support, Cowork actions).

Microsoft’s list covers payments, sending your personal details to websites, actions involving other people such as sending email, and “Account altering actions, including deleting files, modifying cloud storage, canceling subscriptions, or changing account settings.” The approval box previews what Cowork plans to do, and you can pause a task or cancel it entirely.

Two details widen what one approval covers. For scheduled tasks, “Copilot may ask for required approvals during setup so the task can run unattended in the future.” And at work, Microsoft’s FAQ describes an option to “skip the prompt for similar actions for the rest of the current session”.

On the web, until Microsoft’s remote browser arrives, Cowork can use your own Edge, with “the sites you’re already signed in to.”

Both: the result is yours

Microsoft: “You are responsible for actions Copilot takes on your behalf.” Anthropic: “You remain responsible for all actions taken by Claude performed on your behalf.”

Davidov’s Cowork asked before deleting too. So how did 15 years of photos go after one yes to some temporary files? The rest of this guide goes through what happened, and gives you a check that lists what’s gone after a job.

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