Bluetooth device needs to be toggled on repeatedly in order to connect.
When attempting to connect to a Bluetooth device, you must repeatedly click the connect button for it to work.
I've attached a video to visually show what I'm seeing.
Workarounds
- Blueman - https://github.com/blueman-project/blueman - Works on the first attempt every time.
- Bluetooth Quick Connect extension - https://extensions.gnome.org/extension/1401/bluetooth-quick-connect/ - Again, works every time. Also, I really like the UX of having the connections available in the drop-down. Much like VPN is today.
Also, I've created a reddit thread with replies indicating that this is a long-standing widespread bug - https://www.reddit.com/r/Ubuntu/comments/fktxp3/is_there_a_way_to_fix_this_annoying_bluetooth_ux/