Hello ​@Nikow, can you elaborate on how TailScale was initially installed and the issues you are seeing with the uninstall?

The TailScale documentation does indicate you are correct in your summary though, as whilst it allows the app to be uninstalled, the remainder has to be removed administratively; please see the below:

https://tailscale.com/kb/1069/uninstall?tab=macos+%28app+store%29

My recommendation is to contact TailScale for a scripted solution which EPM-M can then target, if you require users to self-uninstall.

In most cases, this is the standalone installation and not via the App Store.
If the user drags the TailScale app into the trash in the application directory, a message appears that the network extension must first be uninstalled. If you confirm this, an admin query appears. The Network Extenions cannot be deleted via the macOS system settings because the user has no permissions to do so.

Hello ​@Nikow,  can you try to disable the network extension from System Settings? This may be possible using an EPM-M rule, as per the below:

Type: System Preference Pane
Name: Privacy & Security
File/Folder Name: /System/Library/ExtensionKit/Extensions/SecurityPrivacyExtension.appex
Application Requests Authorization: *

If this allows you to disable the extension, does it also allow you to delete it?