Plexamp for Iphone does not sync history unless toggled

Plex Labs
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2

Play history syncs in real time as-it-happens, unless there is some sort of network issue, in which case it stores them offline and a successful connection to server (e.g. going back to home screen) will cause the plays to be flushed. Your Plexamp logs would indicate why it went into “offline” mode but it shouldn’t happen generally.