If you modify sort in a Playlist you can revert to playlist sort using sort on #. It also indicates the actual order of files on the Playlist so you know this even when sorting. Yes, once you update the Playlist order # will change to reflect this change of order of files.

So when you're in a playlist and you right-click the column header and select "Choose columns/sort" it brings up a dialogue box where you can choose a Sorting option for that playlist as well as choose what columns are displayed:



The Selected Columns option is always remembered for that playlist but the Sorting always reverts back to "#". Isn't it redundant to even have that Sorting option in the dialogue box then? It makes it look like it's a broken feature by reverting back to "#" every time.

No, it's not saving a sort order, Playlists are just a list of files. Saving the sort just reorders the list of files, but no sort is saved.

But I can change the sort order of any playlist by clicking a header, e.g. Album and then clicking the Save New Order button. When I go back into that playlist, it's still sorted by whatever I previously chose so MM must be saving my sort preference no?

The thing is there is no sort stored with the Playlist, it is just a list of files. Thus MediaMonkey isn't aware of a sort order for the Playlist which is why it can't be displayed.

In different playlists I set the sort order to different things depending on what the playlist is. So for example I might click the Artist column to sort on Artist name and then I click the Save New Order (disk) icon so this is remembered for that playlist. At this point there is a little 'up arrow' on the Artist name heading to show that the playlist is being sorted on Artist name. Also if I hover over the column heading it correctly says "Sort order 1. Artist ascending".

But if I then move to a different playlist and then come back to that first one, although the sort order is remembered and displays correctly, the up arrow has gone so I have no way of knowing what a particular playlist is sorted by. And if I now hover over the column heading it always says "Sort order: 1.# ascending" even if it isn't sorted by '#' number.

Also at this point if I right click the column heading and click "Choose columns/sort" it shows the sort order as "Sorting # A.Z" even if I originally sorted by something else.