When screen sharing a specific window on macOS with Zoom or Skype/Teams, they draw a red or green highlight border around that window (which belongs to a different application) to indicate it is being shared. The border is following the target window in real time, with resizing, z-order changes etc.
See example:
What macOS APIs and techniques might be used to achieve this effect?
You can find the location of windows using CGWindowListCopyWindowInfo
and related API, which is available to Sandboxed apps.
This is a very fast and efficient API, fast enough to be polled. The SonOfGrab sample code is great platform to try out this stuff.
You can also install a global event tap using +[NSEvent addGlobalMonitorForEventsMatchingMask:handler:]
(available in sandbox) to track mouse down, drag and mouse up events and then you can respond immediately whenever the user starts or releases a drag. This way your response will be snappy.
(Drawing a border would be done by creating your own transparent window, slightly larger than, and at the same window layer as, the window you are tracking. And then simply draw a pretty green box into it. I'm not exactly sure about setting the z-order. The details of this part would be best as a separate question.)