I believe I found the solution to this problem, which was bugging me as well, and the solution is... patience!
Here is what I did:
- Turn off your Powerbeats
- Un-pair the headphone from ALL devices connected to my iCloud account. Even the living room MacMini which I had never used with the headphone, but which had received the configuration through iCloud.
- Wait about an hour so things settle
- Turn on the headphone and put it in pairing mode near your iPhone
- If bluetooth is on, the iPhone will automatically recognize your Powerbeats and configure it (strangely enough, an iPad running the same version of iOS won't do the same)
- Other iOS devices (iPad for sure, AppleTV not so much) will receive the bluetooth configuration through iCloud almost immediately
- Macs won't, though... It took me 2 or 3 restarts on MacOS for the headphones to appear in my list of bluetooth devices. RESIST THE TEMPTATION TO ADD IT DIRECTLY THROUGH THE MAC BLUETOOTH PREFERENCES!!!
- Same with Apple Watch. It also took 2 or 3 restarts (turn off with the side button and then back on again) for the headphone to appear, but it did. RESIST THE TEMPTATION TO ADD IT DIRECTLY ON THE WATCH BLUETOOTH PREFERENCES!!!
Now, it all seems to be working fine. Any of the 4 devices I use (Mac, iPad, iPhone, Watch) can catch the bluetooth connection from any of the others.
Patience, little one... That is the key to mastering iCloud.