Still happening with 1.8.6, just tried Superhot VR and it has the same problem. System report directly after this issue occurred (Superhot still open): https://gist.github.com/Zamundaaa/636882d74d628cc20b53193b0aa51b21
Just had it happen with Arizona Sunshine (SteamVR Beta 1.8.11) where it just didn't display anything at all for a good while and then showed a message saying it didn't find any VR headset.
Seems to be fixed as I've not seen this in some time now.
Nothing extracted yet.
System Information (please complete the following information):
Games sometimes don't connect properly to SteamVR. They can apparently initialize OpenVR properly and so on, the game window pops up with the HMD sitting at 0,0,0 I presume and that's it. The game produces sounds and seems to continue just fine, but it won't get any input whatsoever from SteamVR. In the headset there's then no image and while the game is starting it also doesn't show the loading screen thingy in VR. After this happens once no game is able to connect anymore until I restart SteamVR.
Edit: also wanted to state that Pavlov VR triggers this particulary often.
Note: Commenters who are also experiencing this issue are encouraged to include the "System Information" section in their replies.