External Monitor Won't Wake from Sleep
Main Mac = iMac Pro
External Monitor = iMac mid 2011 (27inch)
Connection via Thunderbolt 2 cable with Thunderbolt 2 to 3 adaptor on iMac Pro end.
All cable and adaptor from Apple
iMac mid 2011 won't wake from sleep
Work around = press CMD F2 again (only works on original apple keyboard)
It will wake the external monitor and exit the external monitor mode,
Just press CMD F2 again to get iMac mid 2011 back to external monitor mode
Don't need to unplug cables
Don't need to reboot
Tried to press power button on iMac mid 2011 before, but didn't work
hope this helps.
iMac Pro, macOS 10.14