Same issue. Surface Pro 7, Dock 2, microsoft usbc->hdmi converter, plugged into dock 2 usbc monitor port.
Worked for several months. No longer works since March timeframe. Replaced Dock 2, reset surface. Still same issue. Confirmed adapter and hdmi cable work to monitor through direct connection to pro 7 usbc.
No way works through dock2 any longs.
Seems like a firmware or driver issue. two chats with support and tired of the same "make sure you have all updates" etc.....
When is this going to really be addressed by Microsoft. This issue is pervasive when searching the internet.