Thanks, problem reproduced, tracked as: https://www.ventismedia.com/mantis/view.php?id=16906

[list=]The "Playing" play list contains all the songs MM5 will play and the order it will play them in (assuming the user does not choose something else to play).[/list]
[list=]MM will normally continue from where it was last playing after quitting and restarting.[/list]
[list]This no longer occurs. MM5 always starts playing again from the same song when restarted[/list]
[list]The task manager shows all MM5 tasks quit successfully[/list]
[list]On quitting persistent.json, MediaMonkey.ini and mediamonkey.m3u8 are updated[/list]
[list]While playing MM5.DB is updated[/list]

What do you mean with Play Now position, if you mean which file was playing, does MediaMonkey disappear from Task Manager on close?

MM5 v5.0.0.2264 is also not saving the play now position for me.
Using Windows 7 64b professional
Similar behaviour was fixed in v5.0.0.2206 https://www.mediamonkey.com/forum/viewtopic.php?f=30&t=94846&p=462430#p462430

Good point. Probably just didn't shut down cleanly. I will try to verify in Task Manager next time.

Did MediaMonkey properly close down (ie. disappear from Task Manager) when this happens? I've seen it with crashes, but otherwise position seems to be remembered correctly.

Build 2264 - Windows 10 Home (Version 2004)

I have noticed this happening a couple of times recently.

I listened to one of my playlists right to the end of the playlist. I then shut down MM5 and shut down my computer as I was heading out.

When I get back, I open up MM5 and the Now Playing window thinks I still have four tracks to play of the playlist I finished earlier.

It's a minor problem, but seems that something is going wrong somewhere.