SO... After many weeks of having a dead-beat Apple Watch I finally got the update to work without prompting me to connect to the internet. It took going through most of these responses here and combining suggestions. Here's what worked for me (copy&pasted from posts): Hard reset & wipe all content from the watch. You do this by:Turning off the watch completely from the side Botton below the digital crown. Turn it back on, and when you see the apple logo pop up, press and hold the same Botton for 30+ second until it asks to wipe all content of the Apple Watch. Shut down Watch again. (Do not hard reset) Hard reset the phone. Steps are: Press Volume Up and let go. Press Volume Down and let go. Press and hold the side button. NOTE*: This does not wipe any data from your phone" Once powered back up, sign out of iCloud completely. Go to settings click on your name scroll all the way to bottom and click sign out. **This was nerve-racking, but will NOT erase any information from your phone!  Once signed out of iCloud, shut down phone again (do not hard reset). Go to settings general shut down iPhone. Power up Watch and place on charger.  Power up iPhone sign into iCloud/AppleID  On iPhone, make a Network Reset. *This was the step that finally made the difference! Go to settings wifi the “i” next to the network you’re connected to “forget this network” Connect back to your wifi network and enter your password.  Go to the watch app and start the pairing process. ** Make sure to press the option to do it manually and enter the sequence of numbers displayed on the Apple Watch.  From there it asked me to go through with a software update - and success! Godspeed ya'll.