Each iOS and MacOS release reveals a new suite of tools and capabilities, but also new challenges and complications (and sometimes bugs). The saturation of iOS and Mac products means more and more people own Apple devices-which means more and more people need help using them. Then, realizing how long I would have to wait for an appointment, I gave up and Googled “Apple-certified iOS support Portland Oregon.” Within half an hour, I was able to make a next-day, one-on-one, in-person appointment at Geeks4Mac, a local Apple support shop. After attempting once again to navigate Apple’s website in order to get a Genius Bar appointment, it became clear I would mostly likely need to lie and say I was having a hardware issue and not one related to software. Some hours later, I received a reply with a link to an Apple Forum discussion about disappearing voicemail messages. I can't say enough about them.“There’s a file size and a file name,” I typed into the empty white space on Apple’s support website, “but nothing happens when I hit play.” I sent the note after audio I’d recorded on my iPhone using Apple’s Voice Memo app malfunctioned. Of note though: The Apple online support people were fantastic! Very knowledgeable and incredibly patient.
And, trying to do both at the same time likely slowed down both as they competed with each other.
The issue appears to be: Even though the phone had been "restored from its iCloud backup" it was still downloading tons of data from both Apple Music to my iPhone library as well as from the health app - and it, apparently couldn't do that and download the data needed to restore the pairing with the Apple Watch simultaneously. The next day, it paired immediately and without any problem. That went on for 3-4 frustrating hours till I noticed that the Health App was still being restored with my data So, we gave up. The problem seemed to be a network thing where it just couldn't get the data from my WiFi - it would start and then just hang. But, when it wouldn't pair I contacted Apple Support and they tried every trick in the book - but it still wouldn't pair. When I got home I restored my iPhone from its iCloud backup and then began the process of pairing it with my Apple Watch. A wrinkle I ran into when Apple replaced my iPhone 6+ was pairing the new phone to my Apple Watch.
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