Sync is confusing me, am I doing it wrong?

I started to test out Syncing some content to two devices (Jake’s Galaxy Tab and Ryan’s Galaxy Tab), for two different users (Jake and Ryan). Only one user was used on each device. Tautilli shows that the seven files were in fact converted for Sync.

However the screenshot shows the files for “Ryan’s Galaxy Tab” are not indicating they have downloaded, I have since interacted with Plex player on that tablet since the conversions completed. I used the same account (Ryan) to interact with Plex player on Ryan’s Galaxy Tab so would have assumed that TWO files would download for him on that device.

I watched the conversions happen on the Plex Media Server using my account (owners account) however the Optimised Versions page is practically empty with the owners account on PMS, like so:

Should I see all converted files for all devices and users by logging in to PMS with the owners account? And how do I tell if the files are downloading for my managed users on their devices?

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