One way would be to duplicate the layer several times and apply every time 1 pixel plus on the x axis. When you rotate it at 90 degrees, the stroke is not disappearing. Not a great workaround though.
The other way would be that you take the mask out of the middle of the composition. (Change the Position of the Layer)
Then the angle of view to the layer changes and the stroke appears even at 90 degrees, of course in perspective.
Sorry for the bad english 🙂