Using Sync: Is everyone forced to access Plex multiple times?

I’m not sure whether this Plex behavior is specific to me or it is part of its design. I find that if I want to SYNC a video locally on my iPhone it is always a two-step process. The first is to select the video. Once I do I can see in SYNC that it is converting. However, it will never get download to my device until I got back in to PLEX on it. Once I do I see that the conversion is complete and the SYNC process for this specific file is at 50%. Then the downloading starts until it completes.

Is this normal behavior? It would be nice to just choose multiple videos and set it and forget it, but I’ve never found that to be the case. It takes quite a bit of manual intervention for multiple files.