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I've had the same problem for ages, don't know what changed to make it start. One thing I've noticed is on the files that skip if you right click them and click 'create AAC version' (might be a different format depending on your import settings) the new song you created will have a total time of 4:37 every time (it only seems to happen to songs longer than 4:37).

I'm curious if anyone else gets the same thing.

My solution which seems to be working so far (someone already suggested this) is every time you import music into iTunes use a different application (I use MAX) to convert the files to a different format (it seems to be MP3 thats the problem so I use Apple Lossless but its up to you) and then import them to iTunes. To find all the songs that are already acting up you could select all, right click and create AAC version. This will duplicate every song in your iTunes library and then you'll have to look through every one for songs that changed to 4:37 long and reimport. For all the other songs you'll have to delete all the duplicates so this could take quite a while (to change the format of the new versions, the option is in iTunes preferences>general>import settings (bottom right) if you're using iTunes 11.4).

Hope this helps
 
(3) A group of songs all imported "at the same time" all had a similarity about the point at which the skip occurred -- I think they all skipped at the same number of minutes/seconds into the song. Songs that were shorter than that length did NOT skip and were fine.

This just happened to me too. MacOS High Sierra 10.13.3, iTunes 12.6.3.6. Doesn't happen all the time, but if it did happen then all the songs imported "at the same time" would skip to the end right around the 1:31 mark.

The only thing that worked for me:

1. Click on a song, select "Show in Finder"
2. Delete the songs from iTunes (but retain the files)
3. "Re-import" the songs by dragging the files back into iTunes
 
This is exactly it. iTunes 10 didn't have this issue.

I'm still using 10.4.1 on all my Macs, from 10.5.8.11 to 10.12.6. I don't trust HS yet.
The problem does show up in 10, it's just once every 500 songs or so.
Having just spent 2 hours correcting the chaos of a 1300 song crossplatform input, I'm fairly certain that when you overload the import function, it messes up. -I made a mixtape playlist on my Samsung, forgot how I made it, so re-imported to a playlist in my master library of about 32k tracks.
I should've imported the collection in 100 track chunks. -PITA

Oh yes. Before you do anything major, make a backup, and not one of those Time machine thingees, a Real backup. Saved my posterior here.
 
I'm still using 10.4.1 on all my Macs, from 10.5.8.11 to 10.12.6. I don't trust HS yet.
The problem does show up in 10, it's just once every 500 songs or so.
Having just spent 2 hours correcting the chaos of a 1300 song crossplatform input, I'm fairly certain that when you overload the import function, it messes up. -I made a mixtape playlist on my Samsung, forgot how I made it, so re-imported to a playlist in my master library of about 32k tracks.
I should've imported the collection in 100 track chunks. -PITA
Even after these few years from that quote (2014, holy ****...), I've gotten a new laptop and rebuilt my library from the ground up (mainly cause I had a long of crappy 192/320 singles and whatnot from the 90s), and this still happens. Less frequently, but nevertheless its just a hit or miss when iTunes decides its done playing a track halfway through and just skips to the next. The only thing now is iTunes does this everytime I open it (even when i let it finish, every time i launch it, it does this all over again):
Screen Shot 2018-02-26 at 1.43.56 PM.png

I don't know what it means.

No one on Apple support forum knows what it means.

Pretty safe to say that even Apple themselves probably doesn't even know what that means.

Anyways, I just tolerate it or use my iPhone/BT headphones.

and not one of those Time machine thingees, a Real backup.
Whats the difference?
 
Whats the difference?

When I'm writing on a project, TM usually gives the option of losing no more than an hours worth of work.
-I test that pretty regular, just to see that it hasn't gone off to LaLa land.
On major restores my experience is that TM fails more often than it suceeds.
So before I do anything drastic, I do a full SuperDuper! (or CCC) backup of the whole drive in question, and test that before I go after the actual problem.
That way things cannot get worse than they already are.

Hit a backspace while the name of a playlist I was working on was selected the other day.
Bang! All gone! Why Apple never got around to sticking an "Are you sure you want to...." dialog in there before it Kills an entire playlist still baffles me. It's like 10 minutes of coding, tops.

Gapless used to be a real thing for symphonies and such, where you didn't want 2 seconds of silence between consecutive notes in different tracks. Apple took out the checkbox for setting an album as gapless, but still does some sort of computation automatically. It's just an artifact left from the olden days, like your appendix.
 
Oh boy -- this sounds like the problem I had many months ago. I hope I can give you some insight, as it was very frustrating to deal with (although I eventually resolved the problems with the tracks).

I had found a very useful thread on the Apple support forums. However I had to pay attention to the info from posters who had "the same problem" and filter out those that had similar-sounding-but-different problems. Of course you'll have to apply that filter to me too...

Going by memory, "the one true problem" seemed to have these characteristics:

(1) It could occur in many versions of iTunes. Some sufferers were on the latest version, while I was (and still am) on iTunes 10.7.

(2) A given song would always prematurely end (skip to the next song) at the same point in iTunes.

(3) A group of songs all imported "at the same time" all had a similarity about the point at which the skip occurred -- I think they all skipped at the same number of minutes/seconds into the song. Songs that were shorter than that length did NOT skip and were fine.

(4) Playing the .aac or .mp3 file itself with another player worked fine (no premature end) -- even if you used finder to get the file out of the iTunes Library. (Thus, the aac or mp3 file itself was NOT the problem.)

(5) You could fix a given song as follows: within iTunes, right-click a song and pick "Show in Finder". Then re-import THAT SAME FILE into iTunes. I think I just dragged the shown file from finder and dropped onto the iTunes Library pane.

(6) For me at least, the problem never occurred when I ripped a CD into the library. It only happened when I imported an album's worth or more of mp3 files by dropping them in iTunes. Then, I would consistently get *some* tracks with the problem, but the exact minutes/seconds at which the early termination occurred would be different than the last time I tried importing the same files (thus more or fewer of the tracks might exhibit the skip due to the length of the tracks and the new timing of the skip).

(7) An early termination was more likely to occur in the longer songs. I could often find if an import had a problem by picking the longest song, setting the playhead near the end of the song and hitting play. If it immediately skips to the next song, you've found one.

(8) Oh, some sufferers were using iTunes Match and at first thought it was the culprit, but that turned out not to be the case (at least for "the one true problem"). :)

From these symptoms, I think that the problem is not anything in the .aac or .mp3 file itself. Rather, I think some values are set incorrectly in the iTunes Library File itself (sorry don't remember the filename -- .itl? there is also an XML version of it but that's not the exact file I mean). Some info about a song is kept in the song file with ID3 tags, but some other info about a song is kept in the iTunes library file. This is why re-importing the exact same song file can fix the problem -- because the info in the library file is re-written.

As I said, I never had a problem importing from CD or importing one file at a time. I think there is a very subtle bug in iTunes where the importing goes awry when certain timing or load conditions are met when importing multiple files.

My only solution was to either import from CD, import one file at a time, or check for "problem" songs and fix them as in (5).

I hope you don't have the same problem because it was a real pain in the neck, but if you do I hope this helps. Good luck!

Just started experiencing 'the one true problem' this week - April 2020. I'm on Mojave 10.14.5 with iTunes 12.9.5.5. For me almost every imported file was skipping on to the next track at 2.17. I agree with your analysis - it's nothing to do with the files themselves, its a meta-data issue. The good news is I seem to have identified where the bad data is sneaking in!

SOLUTION: On importing an album folder (by drag and drop onto the iTunes window), wait until all tracks have copied, then look at the top right of the iTunes window. You should see a new temporary button appear, with a rotating circle on it. Click on this, and an 'Activity' pop up will appear, bearing the words 'Determining Gapless Playback Information'. Hit the 'X' button next to this the cancel the process. See attached image. Your tracks will now all play to the end.

Screenshot 2020-04-10 at 12.46.17.png


in my case, the clue that iTunes has thrown a moody is that the 'Determining Gapless Playback Information' process is clearly attempting to repeatedly re-do the last 600 or so tracks I have imported, and has arbitrarily decided that all tracks are 2 mins and 17 seconds long. Perhaps by cancelling it for a while it will eventually right itself. In the meantime, bear in mind that your newly added songs will not crossfade - but for me, this is bearable when compared with all the tracks being borked!

Hope this helps somebody.
 
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How do you get the whole library to work correctly, do you remove then re import them using this method?
The skipping is VERY annoying.

The dredge is worth it for fixing this problem if it can be fixed.
 
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