Is there a way that Plex remembers my place in a playlist that I want to watch over time

When I watch a play list for the first time it recognizes that it is part of a play list and can navigate to the next media file. If i exit the player and re enter, the file that I was in the middle of watching shows as being partially watched but it is not associated with the playlist that it is in. Is there a way that it will remember that it is in the play list and if I finish that file that the next file in the playlist will show up in the on deck section. Any assistance would be greatly appreciated.

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If you want to continue playing the items in the playlist, then choose to finish playing the file from the Playlist. It will remember it’s position, so you can continue playing and when finished, the next item plays. No need to worry about On Deck items.

I have this issue too. Playing from the on-deck or Continue Watching options do not continue through the playlist. To dig into the Playlist is the only way to get it to continue correctly, but there is no way to know which episode one has left off on as it doesn’t show episodes as played or tell you where you are in the playlist at all. The playlist feature needs a whole overhaul. I watch my playlist on different devices and each time I switch, I have to spend 10 minutes scrolling through my playlist to figure out which episode I left off on and if I’m in the middle of an episode, it won’t resume from where I left off either.

I have a playlist of the Arrowverse, which includes 4 shows and many seasons of each show totaling hundreds of episodes in a playlist of specific order. Impossible to remember where I left off at. Would love to see some major improvements in this section of the product.

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I had this same problem recently, and even posted about it. I also was using the Arrowverse as my example.

If you don’t care about order being super exact, then you can make a Smart Playlist following this really great guide that @OttoKerner was kind of enough to make:

http://forums.plex.tv/discussion/299318/watch-crossover-episodes-of-several-series-in-order

However, as I mentioned in that thread, while Plex can sort by Air Date it cannot sort by Air Hour so things like crossover episodes that aired back-to-back on the same day can end up out of order. Also, there’s no way to manually edit a Smart Playlist, so you can’t just fix it.

However, the Smart Playlist is really cool in that you can set it to remove episodes from the Playlist after you watch them so you can easily pick up where you left off.

Right now what I’ve been doing is just looking at my On Deck to see which episode of the Arrowverse I left off on, and then scrolling down the non-Smart Playlist to start on that episode.

So, in it’s current state, there’s a trade-off and you have to pick one or the other:

Option 1) Manually create a giant playlist in the correct order, but know that you’ll have to remember where you left off, or at least try and figure it out.

Option 2) Automatically generate a Smart Playlist that removes episodes after you’ve watched them, but might give you an episode or two out of order, so you have to kind of pay attention to where those crossover events are and make sure you skip ahead on your Smart Playlist when you get there.

Since I already sorted like 40 of my Arrowverse episodes before I understood the limitations I went with Option 1, but if I had it to do over I think I would go with Option 2 and just write a note somewhere on the few episode numbers I needed to skip and go back to.

I know the Plex devs are massively overwhelmed with other things, but hopefully when stuff calms down they can give some attention to the Smart Playlists, because a tiny bit of love would go a long ways towards making them so much more incredibly useful.