So maybe i understood something wrong or maybe my settings are way off. Any way, i need your help.
I have two issues:
When i add a new show it SOMETIMES get's shown in "Latest Media / Latest Shows" sometimes it does not. For example, yesterday i added The Office, it was added to latest shows immediately, today i added Dracula and it's not added there despite me being able to find and watch it.
When watching an episode from a season that is not the very first it, the next episode will not be shown in Continue Watching. For example, i have all the Dimension 20 Seasons (i pay for Dropout but their video player is abysmal). Now i started to watch Season 20 and didn't watch the seasons before that. I watched the first episode of it, but it won't show me Episode 2 as "Continue Watching" or "Up Next"
Personally I have no foxes for you, but these are issues I've never seen myself. Perhaps there's simply something wrong with your install and a clean reinstall would fix things.
For the second point, you can mark the earlier seasons as viewed (click the checkbox at the season level, or even at the show level and then uncheck it on the latest season).
Just found the actual issue, it was because the episodes are pretty long and the threshold for it to be added to continue watching is expressed in % and not in minutes or seconds.
So it was at 5% which can be pretty long for a 2 or 3 hour long episode.