Is your Pebble Steel Stuck in the Recovery Mode Loop?
I recently ran into an issue with my Pebble Steel where the watch would not get out of this Recovery Mode. Every time I tried restarting my iPhone and rebooting Pebble (simultaneously hold the back, up, and select buttons for 10 seconds). However this was not working, here are the steps you need to get your Pebble or pebble steel out of the recovery mode loop:
Step 1 - Forget the Pebble Bluetooth Device
First, forget the pairing on your iPhone. Navigate to Settings >> Bluetooth >> Click on the Little info Icon Next to Pebble EA45
Now to the right of Pebble EA45 >> Forget this Device Repeat same process for Pebble-LE EA45
Step 2 - Turn off Bluetooth then Back On
Step 3 - Relaunch the Pebble App on your iPhone
Relaunch your Pebble app and pair the devices again. Please try the update again.
After you have successfully re-connected your watch to your phone, you should receive a prompt about the update.
If you do not receive the message to upgrade, you can force update the firmware on your Pebble: Main Menu >> Support >> Update Your Pebble >> Check Now.
Step 4 - Finish the Upgrade Process!