I've also noticed this before. I haven't looked at the situation lately because I typically don't use the Art view.
But it does seem to occur for no "apparent" reason.

Good day Lowlander,
Sorry for the late reply, (personal affairs), in answer to your question, I am running version 4.1.11.1783. I always update when there is a new version, and yes my library is maintained with complete optimization checked. I've just started up MM and the last album played comes up on screen with an image of the disc and not the front of the album. Basically as usual. I can't seem to bottom the problem.

Which version of MediaMonkey and have you recently run File > Maintain Library with complete optimization checked?

I notified this fault on the forum on 1st July 2014, under the title 'Artwork forgets it's given order'. I was given a multitude of suggestions to help correct what I believe is a bug, but all went quiet on the subject after 11th August of that year. After trying all suggestions (gratefully received) and failing to rectify it, nothing more came forward from experts on this forum to help rectify a fault which certainly did not exist on earlier versions of MM. I have entered music as new entries in the library following all the guidelines and still find that after a given search using full or part artist or track name, it's usually the first album at the head of the list that appears under 'Art & Details' view that is the culprit, (not always, sometimes there are various). It's the search that surrenders the fault, not viewing the lists directly from the music directory, because by clicking on the artist title of any of the albums displayed by search, in the new list that same culprit usually correctly shows its front and not incorrectly showing other art on the tag, (I find that it's not only the back but sometimes any other art in a random manner). I don't know whether this provides a clue to the fault or not, but to date none of the updates of MM seem to have addressed this now long-standing problem. Developers please note. Also we still have 'MM not responding' regularly or hanging. Sorry to say so, but MM is less stable than it was.
Waypointwatchman

Thanks again Peke,
I'll certainly be converting my WAVs to FLAC.

Now then, the problem persists. I have just deleted from the library all the albums from one artist. All the music files are mp3 format. I checked that all images are correct and are present in the folder. All other images saved to the tags have been removed, and all images have been given an order that has been applied to all files on the album. I then performed a resync as suggested. On adding the next album into the library I then see that the previous album is immediately displaying the incorrect order again, and then the next and so on. I reiterate that I have never had this problem with previous versions of MM, only with the version mentioned above and the latest one that I have upgraded to. I cannot believe that other users have not witnessed this problem and can only believe that we have a bug that needs a fix. I am loath to leave MM, because the competition is nowhere near as good, but this problem is very, very frustrating.

To Sync Tags select tracks and press CTRL+S I just tried and Album Art is Saved in MMW properties order.

RE WAV: I suggest converting them to FLAC, much better and still lossless.

Thanks Peke, that's informative and helpful, but am I missing something here? I have cleared tags and rebuilt them. I haven't resynchronized them, (I need a clue on that one), but after a rescan, why would they come back 'in the order of the tags' incorrectly. I've just cleared them and put them right. Is it the synchronization then? I think I am missing something because I have thousands of files and in years of use MM has never done this before.

FYI WAVs can't have embed Album Art and if MP3 have incorrect order of AA in tag you need to clear tags and resync in order to fix them as each time you rescan files order will be as it is in Tags.

I 've just done another check. I have an album copied in two formats within MM, an original WAV for listening to lossless reproduction, and mp3 for transferring to mobile devices. Wav is behaving itself and the tagged images of the mp3 formatted copy are consistently coming back in disorder no matter how many times I correct them. So it appears that mp3 is the format that is problematic here.

waypointwatchman wrote:I cannot find any examples of WAV format misbehaving at the moment.

No probs with WAV is good, as they can be very problematic.
What about WMAs as Nohitter suggested?

Nohitter,
I've just done a test on searching artists and am finding that the artwork affected, and I have some persistent offenders that will not conform, all belong to mp3 category. I cannot find any examples of WAV format misbehaving at the moment.

What type of files? This was reported some time ago for WMA files and determined to be a bug with the WMA format.

Here is more detailed behaviour now noted of tags that are properly labelled and clean of rogue files in their folders.
After a search is made using any of the fields for an artist, the following is the result:
'Show art with details' selected - art column has random artwork showing, but never the cover, whilst the 'Now playing' art box always shows the cover correctly;
After the tag is corrected using 'properties', the former list of results which always showed albums files together, now displays as individual file results only and the first result is correctly showing art. When 'show more from this album is selected', the artwork is correct and full albums appear again. New search of same artist, artwork correct. Shut down and start again, we start with the same problems from zero yet again. It seems incurable.

I've tried all that has been suggested, i.e. removing the MMCache*****_* folders from the MediaMonkey Temp folder, (there were very few files here) and I've been running with File > Maintain Library complete optimization checked. I was going to say that this has improved the odd situation when the program hangs, but today it hung again, just as I was removing an album yet again to try to re-add it and let Media Monkey sort automatically the order of images. I'm just playing catch up because Media Monkey will do it again and again afterwards and I cannot fathom the problem. The situation is this:
I am using Art with Details showing;
I have the tag images properly sorted, in fact the example album that I'm experimenting on is one that has just 3 album images in the folder, front, back and label, so that it makes the test very simple;
No matter how many times I correct the order, on the next search, it will return the album with the label as principal image;
When I remove, add, check order and do search, it returns wrong again;
What is more, when I remove the album to try again, the next folder in the library that shows on screen after the removal (from library only) returns its images in the wrong order too;
I've just done the last test and Media Monkey hung and did not want to play. After a very long wait I was forced to shut it down via Windows Admin.
Hence I write again with no idea how to correct this.
I have spent much time gradually recorrecting file images and leaving a check symbol on each file. I know that these are correct but they are always included in the ones that return a false order.
I am running Windows 7.

Note that MediaMonkey chooses Artwork from a single file from the Album, thus if a single file has Artwork wrongly sorted it could be the culprit.

I'd suggest to try removing the MMCache*****_* folders from the MediaMonkey Temp folder (location is set under Tools > Options > General). You may also want to run File > Maintain Library with complete optimization checked. Lastly it doesn't seem you mentioned the View (Art or Art with Details you're using.