I have a similar issue, no with Apple Watch, but with Bluetooth devices in general - whether it's my bluetooth earbuds or my bluetooth car connection. If a song pauses while connected to Bluetooth, I can't resume playing unless I tap Play/Pause on my iPhone about 4 times. It doesn't respond to Play/Pause from my earbuds, so it has to be done from my phone screen. I have to stop what I'm doing to resume the song from my phone. ... View more