Situation is that I watched an episode today from a downloaded/synced file on the iOS Emby app. Emby server had the episode marked as watched (which is great I wasn't sure it would do this). I ran both Trakt scheduled tasks and it synced the watch to Trakt however the time and date of the watch is "Monday 1 January 0001 at 10:05AM."
I'd also like to say thank you so much for your support recently. I've just moved over to Emby from Plex and I'm amazed at how good it is. I came to Emby for the Trakt plugin but I'm finding so many other cool features and a really appreciate that the developers actually listen to the community. Rather than reducing features, they're being added. Woo hoo