Hi,
Maybe you've encountered similar problem or at least have a theory why such connection is not working.
Normally I'm using the USB-C to DisplayPort adapter (silver on the photos) with dual monitor setup (DisplayPort daisy chain) and everything is working just fine
I'm condemned to 2 weeks home office (because of corona virus of course) and I have 2 HDMI monitor at home (no DisplayPort), my laptop has one HDMI output on top of the USB-C (DisplayPort)
I have two DisplayPort to HDMI adapters (one is visible at the photo, second one has a cable) and none of them are working with this setup (no screen detected on USB-C)
I've dig up the DisplayPort to VGA adapter and to my surprise - it's working fine!
https://imgur.com/a/kqJG3OL - photos
Any ideas?