Kieshi It is happening on DeoVR on Quest 2 headset. All videos I'm referring to were watched / viewed / revisited only on headset (not referring to web at all here). [That being said, the bars also don't show on web for the mentioned videos either I don't think]
If I had to guess, I'd say videos that were watched partially on headset prior to the feature release are not showing up at all until you enter each individual video and then it loads progress during playback and when you leave it does then show up. For example, basically all videos in my "Watch Later" playlist have some level of watch progress, but basically none have the play bar below the thumbnail until I start playback on the video again.