Hi
Thanks for your reply.
Judging from your problem, I think it may be caused by the converter. Because VGA is the simulator signal output and DP is the digital signal output. There may be compatibility issues that cause windows to not recognize the two interfaces correctly.
You also said at the beginning that your machine is based on windows sever2016, which may be caused by the domain? If you change a computer without a domain, try whether the problem still exists?
Feel free to post back if you need more assistance.
Best regards
Derrick Qian | Microsoft Community Support Specialist
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