iPhone 7 w/ iOS 14.1, Apple Watch Series 5

I've been trying for some weeks now to update my Apple Watch to watchOS 7. Every time I try to install, whether I initiate the installation from the Settings app on the Watch or from the Watch app on the iPhone, the update takes about an 1 to 1 1/2 hours to download, but then throws the error:

Unable to verify update, your device is not connected to the internet.

My device is connected to a home WiFi network. I've tried with cellular both on and off. I've also tried 4 different WiFi networks, from (at least) two different service providers. I've tried with my iPhone on every update from iOS 14 to current.

Some other things I've tried:

  1. Unpairing and re-pairing the Watch
  2. Restarting both devices
  3. "Cold" restarting the iPhone
  4. Charging and completely depleting the iPhone and the Watch twice
  5. Turning off cellular and connecting only to WiFi
  6. Connecting to another phone's hotspot
  7. Turning of the new iOS 14 "private IP" setting

I spoke to an Apple Support Representative by the online chat twice. They run diagnostics on the iPhone and Watch, and confirmed that the "WiFi chip" is fine, and that I was in fact connected to a working WiFi network. They ran me through the basics (restart the device, etc), then escalated to a "senior chat representative", who asked me a series of questions and forwarded me to a "senior phone representative" who performed additional diagnostics. I got nowhere, and was asked to provide a call-back number. That was... four weeks ago maybe?

I'm not sure what else to try. Is there another way to update the Watch? iPhones and iPads can be updated by connecting to a computer with iTunes. I don't believe that's possible with an Apple Watch, however. I'd heard the Watch automatically updates when being paired, but (as I said) that didn't do me any good.

Thanks in advance!


Seemingly the same issue as found here, here, here, and here.

Neither have answers.


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