ITunes linking to JPGs in strange folders & missing files

I was using iTunes on a PC, via a NAS drive where I keep my music. I want to start using iTunes on a MacBook so pointed iTunes on the Mac to the shared music folder on the NAS. I had the usual exclamation marks on some of the tracks, so went in to the folders to locate the files. A lot are now missing from the folders - i.e. half the albums are gone or complete artists are missing.
The second and most strangest part that I cannot understand is that when I look on some tracks in 'Get Info' and 'Where', some of the files have been moved to obscure locations and are showing as jpgs. When I go into the folder, all there is is JPGs! The music plays fine for these files, however I can't locate the rest of my missing files as they no longer have the correct filenames or even extensions. Example below.
Any ideas?
Thanks.

Somehow they got deleted from the PC's hard drive, but iTunes didn't get told about it.
Just find those podcasts in iTunes and delete them.

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Message was edited by: sof6667

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Hi,
I store my itunes library on an external hard drive and I have over 1000 music files which itunes cannot locate even though they are there.
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Re-creating the iTunes Library file
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I have several hundred "missing" files in my iTunes library but they are all actually on the computer. But I don't remember where the were previously. I add dozens of songs at a time to my library all the time and there is no Earthly way for me to constantly remember where they were before. I don't just want to reimport the files because I have several hundred playlists with these files and it would be completely stupid to edit them all one at a time when all I need to do is to move them back to where iTunes thinks they should be. So where is that? The Windows media player has a column that displays file location. Why doesn't iTunes? (This is so stupid. It makes things -not just this- so much easier when you have the file location in the music list in your music player.)
Is there a way to find out where iTunes thinks the missing files should be at?

Chris CA wrote:
How do I find out where iTunes thinks missing files are?
The exclamation mark means ITunes doesn't think they are anywhere.
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I'm not a newbie. I know quite a lot about iTunes. You sound like you don't though because if you did you would know that this is not true. If you "right click - get info on a song" (pressing cancel to the Locate popup) "then view the SUMMARY (not info) tab" you will see "Not Available" where the file location usually is. I wouldn't have asked this question if I hadn't gone through the steps already.
Thanks for trying though. Next time, please try the advice before you give it.
I add dozens of songs at a time to my library all the time and there is no Earthly way for me to constantly remember where they were before
You should not have to remember anything about where they were.
I agree.
Are you always moving them around?
When I install a new hard drive. Yes. I generally keep everything organized and I let iTunes keep the folder organized but several years ago I used windows media player to organize my media.
Frankly I don't know HOW the recent songs/videos/etc. go missing. But some do. Maybe I accidentally move a folder without realizing it. Mistakes happen. Then I need to move it back but since I didn't know I did it in the first place I can't possibly be expected to remember where I moved it from.
Do you have iTunes prefs -> Advanced Keep ITunes music folder organized ticked and Copy files to iTunes ... ticked?
*OF COURSE!* Again, I'm not a newbie.
I have several hundred playlists with these files
Why would you have several hundred playlists?
I don't mean to sound rude but you sound like an Apple fanboy. Are you trying to tell me how I should use my own program? The answer to the question is I am a salsa instructor/DJ and I am constantly adding songs and videos to my library. Every month I have various salsa events, classes and performances that I do. I use my iPhone for the music. I need to maintain the playlists because students/teachers/studios/clubs/bars/churches/etc. call me back and want a repeat of the great salsa night I gave them a year ago. Naturally my playlists are highly organized into folders. So, I still have them and I need them.
Apple has its own ideas about how people should use its stuff but everyone is unique and our needs therefore are unique too. Apple doesn't realize this and still wants us to do things "the Apple way" even though "the Apple way" only works well for people who want their hand held through everything. This is why I say you sound like a fanboy. You don't know my situation and question if I need hundreds of playlists. I do.
I just need an answer to the question.
Thank you for your reply though. It gave me hope, for a time.

ITunes linking to JPGs in strange folders & missing files

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