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Hi Greg Hodge, I want to help you with this question This can have several causes
- Your device is not connected to the Internet at this moment of checking (unlikely, but could be, otherwise check)
- The devices have Windows 10 Home installed. Windows 10 does not support this feature
- The devices used a build that is vulnerable, with problem 21H1 being such a case. Please briefly name the builds installed on the machines There are other ways to join the device. e.g. via the command line, with the following commands: DsRegCmd /join DsRegCmd /status Also, have a look here: https://www.maximerastello.com/manually-re-register-a-windows-10-or-windows-server-machine-in-hybrid-azure-ad-join/ For debugging errors, you can check below event logs: Event Viewer > Application and Services logs > Microsoft > Windows > User Device Registration > Admin I read in another thread that a workaround was to join a different workgroup, which made the option reappear afterward.