Normally this has not been as much of an issue, but recently SteamVR has dramatically decrease the time-out / "sleep" timer to something along the lines of 5-10 seconds... so the headset constantly goes to sleep. Bumping the headset will wake HMD will trigger the auto-entry.
See below gif
Result: Auto-entry to VREditor starts
There's no existing public thread on this issue, so head over to Questions & Answers just mention UE-33970 in the post.