Watch and learn: The Apple Watch needs a better upgrade experience

Though I greatly enjoyed my vacation last week, it ended with a bit of a mishap. On Sunday morning, the last full day of my travels, I knocked my beloved Series 4 Apple Watch off the nightstand where it had been charging and it tumbled three feet to land—screen down, naturally—on a tile floor.

What at first I thought was merely a chipped edge revealed itself upon closer inspection to also encompass cracks along the edge and across the watch’s face. Alas, my Apple Watch had passed on. It had shuffled off this mortal coil. It was no more. It was…an ex-watch.

So I did what any self-respecting Apple aficionado would do and took advantage of the fact that our flight home had been delayed to order a new Apple Watch for pick up at the nearest Apple Store.

Which is how I found myself sitting outside in the surprisingly pleasant Seattle weather in front of the University Village Apple Store, in possession of a brand new Series 7 Apple Watch.¹

But my troubles had only begun. Because despite the fact that I had the previous evening unpaired my old Watch in preparation for migration, when I connected the brand new Apple Watch—after spending a half an hour charging its low battery, connected to my MacBook Air in my backpack—I found that the only backups it offered to restore from were several years old.

After a moment of stomach-churning worry, I also realized something else critical: all those backups were on very old versions of watchOS. Like watchOS 5 old. At which point it clicked: of course, I’d kept my Apple Watch up to date with the latest watchOS, and the new one I’d just picked up had been sitting on a shelf for probably at least a few weeks, if not longer, and was thus out of date.

Surely, I thought, there would be a way to easily update the watch as part of the migration process. After all, Apple has run into this problem with iPhones over the past few years, in cases when iOS updates were issued before brand new phones were shipped. As a result the company improved its migration feature to update software as part of a restore from iCloud Backup.

Unfortunately, it seems that no similar feature exists for the Apple Watch. Instead I had to go through the following process: unpair the new Apple Watch from my iPhone, re-pair and set it up as a new watch, download and install the watchOS update (which it will only do when the Watch is connected to a charger and your phone is on Wi-Fi), unpair the Watch, re-pair the Watch, and then finally restore from my most recent backup, which this time did show up.

Woof.

All of this was complicated by the fact that I was without a stable Wi-Fi connection all day, meaning it took quite a while to get the update, and Apple Watches aren’t exactly fast at installing software even at the best of the times. Roughly ten hours after I picked up the new Apple Watch, as I was waiting for my plane at the airport gate, I finally had an up-and-running Apple Watch.

This process should be a whole lot smoother. Even if Apple can’t find a way to update the software as part of the migration process—and come on, it should be able to do that—it should at the very least make it more transparent.

When the iPhone first showed me the available backups to restore from, it didn’t even show the backup I’d made the previous night. I totally get that Apple thinks it’s being helpful here: why show backups you can’t restore from? But, on the flip side, why not display all the backups and, say, gray out the ones that are currently ineligible, to at least avoid the concern that a backup has been lost? Heck, go a step further and put a little note that says you need to update the software before you can restore this backup, perhaps even with a link to explain the process. It seems like the very least that could be done.

Perhaps customers aren’t replacing their Apple Watches as regularly as their iPhones—certainly, there are fewer of them out there, so I can see why the company may not have invested as much time in streamlining the update process. But even I, a person who writes about Apple professionally, had to spend a while on Google to figure out what the best way to do this was. That hardly seems like a good experience for a company that prides itself on ease of use.