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Re:macOS Catalina 10.15.5 by lsllc on Wednesday May 27, 2020 @12:10PM (#23325417)
External display wakeup problems have been an issue on many generations of MacBook Pro going back to PowerBooks (even with Apple displays). Very annoying!
Re:macOS Catalina 10.15.5 by thruhiker on Wednesday May 27, 2020 @01:47PM (#23327015)
I experienced this issue using an HDMI to DVI adapter from my 2018 Mac mini to a Dell Ultrasharp display. After purchasing a replacement cable that didn't remedy the problem, I discovered that it's a known issue.

The fix was to use a USB-C -> DisplayPort cable (using DisplayPort via USB-C alternative mode). It appears that the HDMI port can't be used with a DVI converter. DVI ports have been replaced by DisplayPort, HDMI, and DisplayPort for some time but it was still a disappointment.