When i connect my adventurer unit onto the cradle end of the charging cable connected to my Mac, sometimes i don't see the Sports connect app autolaunch. Then I disconnected the watch unit from the cradle to get an Finder "eject" error popup. I then reinsert the unit back into the cradle. This is when either the Desktop autolaunches or still doesn't launch on its own. What's up with the app?
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Superusers
I hope this helped answer your question. If so, please mark it as a solution so others can look for it if they have the same question.