I am having a hell of a time every night getting my cable to attach securely enough to the back of the watch for it to charge. Has anyone else had this problem, and if so, how did you fix it?
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On the ZenWatch 2?
There is a magnetic connection between the watch and the charging cable... If you place it the wrong way, the cable won't connect (the magnet actually repels the connection). However, placed correctly mine actually connects quite firmly. The only thing I've noticed is that if you place the watch down on a nightstand haphazardly, the cable could get disconnected. To this end, I use a watch stand for the ZW2 while it's charging.
Something like these (available on eBay):
(Yes, I know the ZW2 is not in that photo, it's just for example purposes.)
Perhaps there is something up with your charging cable?