The option is already set to "Play Playing Now".
I am using Standard View, not Theater View, by the way.
Generally, the sequence is:
1) Audio files are played, and Zone Switch will change the Zone to "Stereo" (in order to use the Bifrost stereo DAC).
2) When stop is pressed, the Zone is still "Stereo"
3) A video file is played using Windows Explorer (it is not imported because it is a disposable file which won't be watched at a future date, unlike for example a movie). Zone Switch will change the Zone to "Video" during playback (in order to use the PC's built-in Dolby Digital 5.1 Surround DAC).
4) When stop is pressed during video playback, the Zone reverts to "Stereo". If a step is added in between 2) and 3) to manually change the Zone to "Video", using the Zone menu, then when stop is pressed during video playback, the Zone stays at "Video".
So, I want the Zone Switch software to automatically do that manual Zone change, so that I don't have to remember to do it every time.
BTW, if your last sentence is supposed to be true, then it is a bug.