How do "Enable for your organization" and "Run Cowork in the cloud" differ?
The first decides whether Cowork is available in your organization at all. The second is a separate toggle that decides whether Cowork sessions can run on Anthropic's infrastructure instead of members' computers. They are set independently, so "Cowork is enabled" does not imply "the cloud is enabled," and the cloud toggle alone does not tell you whether Cowork is open to members.
Why are the Team and Enterprise defaults opposite?
The documentation states the defaults without explaining the reason. A reasonable inference is that the two plans use different administration models: Team leans toward open-by-default with Owners pulling back as needed, while Enterprise follows an explicit grant model where custom roles hand the capability to groups one at a time. This is inference, not an official design explanation.
How do I let a particular group use cloud Cowork on Enterprise?
Per the documentation there are two steps. An Owner first turns on "Run Cowork in the cloud" under Organization settings > Cowork, then grants the "Cowork in the cloud" capability to the group through custom roles. Doing only the first step leaves group members without the capability, and granting without the master toggle on is likewise ineffective; both are needed.
I am an admin; what should I check now?
First, confirm whether you are on Team or Enterprise, since the defaults are opposite. Second, open Organization settings > Cowork and check that the current state of "Run Cowork in the cloud" matches your company's data-location requirements. Third, if you need the exact behavior of web and mobile when the toggle is off, verify with a test account instead of inferring. Organizations with HIPAA needs should note that cloud is unavailable under local mode.
For administrators, Cowork's cloud execution is governed by a single toggle in organization settings, but that toggle's default is the opposite depending on your plan. That is exactly where internal announcements go wrong.
Under Organization settings > Cowork, "Enable for your organization" decides whether Cowork is available at all. "Run Cowork in the cloud" is a separate toggle that decides whether Cowork sessions can run on Anthropic's infrastructure instead of on members' machines. Cowork being on does not mean the cloud is on.
The documentation says the toggle is on by default for Team, and an Owner can turn it off at any time. For Enterprise it is off by default: an Owner turns it on, then grants the "Cowork in the cloud" capability to a group through custom roles. In other words, the Team question is "do we want to take it back," while the Enterprise question is "do we want it, and for whom."
Cloud sessions let work continue across desktop, web and mobile, and let Scheduled Tasks run with the laptop closed; Cowork sessions on web and mobile run in Anthropic's cloud by definition. So the toggle effectively decides both whether members can use Cowork from a phone and whether scheduled tasks depend on a member's computer being awake.
The documentation says cloud sessions are governed by this control, but it does not spell out exactly how web and mobile sessions behave when the toggle is off. If your compliance process needs a precise answer, verify it on a test account instead of inferring it. One explicit boundary does exist: under the HIPAA configuration for Claude Code (local mode) and Cowork (local mode), Cowork in the cloud is not available, and no setting turns it on.
If you administer a Team plan, members may already be able to use cloud sessions by default; if your company has data-location requirements, you need to act to turn it off. If you administer Enterprise, the default is off, so members cannot use cloud Cowork on phone or web until you enable and grant it. Before you announce anything company-wide, confirm which plan you are on, then decide whether the message is "you can already do this" or "request access from IT."