Presumably you're browsing files (Artist, Albums, Playlists, ect.) in MediaMonkey. In that case MediaMonkey only either plays the selected file or selected file and subsequent files. So if you intend to play all files you'll either need to select the first or all files.

It's been around forever. If you launch MediaMonkey prior to it being closed this has been an issue for a long time.

It was never intended as a method/feature and caused all kinds of scaling issues.

Yes, that's an old build.

Correct, you can't zoom the interface like that in MediaMonkey 2024. You have options for size in certain Skins and Windows DPI/Text Size settings.

Virtual CD has been removed from MediaMonkey 5+.

That happens when MediaMonkey is still running. You should always wait for a program to fully close before relaunching when you're testing things.

I'm unable to reproduce with identical dual monitor. MediaMonkey resizes on the monitor it was resized on. Please capture this in a debug log (step 4b) and attach the log to a Support Ticket.

I'm unable to reproduce with identical dual monitor. MediaMonkey opens on the monitor it was closed on. Maxmized or not. Please capture this in a debug log (step 4b) and attach the log to a Support Ticket.

Could also be iOS 18 being slower. How does syncing more content fail for you?

Have you tried reinstalling MediaMonkey (it's an included Addon)?

Yes.

OS Integration is only available on regular installs. Portable Installs don't have this as they're designed to not integrate with the OS.

If you sort on Album (instead of Path or Filename), MediaMonkey will sort on Album > Album Artist > Disc# > Track# > Title. So filenames don't matter, but tags do when sorting on Album.

You can also use MediaMonkey to rename the filenames to include the Track# (if the tag exists).

You can override the default setting per Type if you wish to do so. This is why there is a global setting and then the option to override it.

Are the Album Artist values for all the files on the Album the same? You need the same Album Artist, and also make sure Disc# is set correctly.