I guess it depends on what product(s) you have and how you are trying to update them. I have 4 Orbit timers and a WiFi hub, and they work and update perfectly well.
The app is a total piece of trash, but the timers are fine (Orbit XD 24634), and respond to the app, both in WiFi (via hub) and Bluetooth mode just fine. They do occasionally time out, so being close to the unit for a Bluetooth update won’t hurt any. Manually, they also work without issue.
All of mine are now over a year old and have been updated a couple of times (not that I’ve noticed any difference from the firmware updates).