Moto 360 software update hangs I have a Moto 360. I get a card saying there's a system update. I open the update and tell it OK to install. I get the red/blue/yellow/green spinning dots and a progress bar. When the progress bar reaches approximately 30%, the dots disappear. The green Android robot appears. He has a hatch in his stomach area, and a red triangular icon with an exclamation point inside of it appears. The watch stays like this until the battery dies (unless I hold the physical button until the watch shuts off). I can then reboot back to normal, but after a few hours (or sometimes minutes) the system update card will appear again and the whole cycle starts over.

What is causing the system update to fail? Are there any debugging steps I can perform?

When I go to Settings, my current software version is 4.4W.1.

I have tried doing factory resets twice and then updating, but the issue persists.

Update-I got in touch with Motorola support. They had me reset the watch and try updating. When that didn't work, they decided to replace my watch. They'll be shipping me a new one.
Never had this problem before, and my Moto 360 updated OK.  I know it is a pain in the butt, but I would do a factory reset on the watch.  The best way to fix problems on these wearables are to reset them - there's no way to debug when they're just Bluetooth.