why does my songs recheck themselves

Not sure. Possibly related to iCloud music library, if you subscribe to either iTunes Match or Apple Music, with more than one associated computer (or device).

Again, don't know why that happened. However, if you are doing that (unchecking songs in your iTunes library) so they do not get loaded when iTunes automatically syncs iPhone, there's a better way. If you want to try this alternative...

First, create a new playlist in iTunes, and call it something like "Songs on iPhone" (or whatever you want). Add ALL of the songs you want on iPhone to this playlist. (In your case, this is all songs that are checked, so you could sort your music library using the checkmark column to get them all together on the list.)

Then, select iPhone in iTunes to show its settings screen in iTunes window. Along left side of window, in the sidebar, under Settings, click Music. To the right, the iPhone's Music settings screen is shown.

NOTE: Songs on iPhone that are NOT in your iTunes library will be lost. If all songs are in iTunes library on computer, no problem.

At the top, the checkbox for Sync Music is probably already checked; if it is not, checkmark it. Below that, choose the option to sync Selected playlists, artists, albums, and genres. Below that, under Playlists, find and select (checkmark) that Songs on iPhone playlist. (If you have other playlists that you use on iPhone, you can also select those playlists.) At the bottom, click Apply. iTunes syncs your selection to iPhone. Going forward, you just need to update the selected playlist(s) in your iTunes library (add/remove songs). The next time you connect iPhone (or click Sync if already connected), iTunes updates iPhone with the same changes. You can leave all of your songs checked in library.

You can also stop using the checkmarks as the way to select syncing for other iTunes media. First, try syncing music using playlists instead of using the checkmarks, to see if that works for you.

Are the songs that are causing you issues songs that you've purchased from the iTunes store? I am having a similar problem with my library since updating to 12.3.2.35 -- songs that I've purchased are checking themselves, and the ones that seem to be doing this are ones that I have edited the metadata in some way (changing the artwork, changing the genre, renaming the file, etc).

In order to prevent the songs from checking themselves, I can no longer be signed into iTunes with my Apple ID.

I am having this same exact problem with a lot of my songs. I have a 64GB iPad so I can get most of my music on it, but I really don't want it all on there. However, making playlists for the songs I want on it would take a ridiculous amount of time, seeing as I have almost 9,000 songs. iTunes has only been doing this since the newest version of iTunes was updated. This is becoming a huge pain because I'm having to constantly go through every single song and check to see if it is rechecked. I don't know what to do.

Since your songs that you want on iPad are currently checked, it would take about one minute to create a new playlist with the same songs.

First, show your music library and click Playlists to show the playlists sidebar. Create the new playlist and name it something like "iPad Songs" (or whatever you want).

Second, show your music library list using the Songs view (to show a plain list with columns). Click the heading for the column with the checkmarks. This sorts the list so that all of your songs that are currently checked are together on the list. Scroll list to see the first checked song and select it. Scroll list to see the last checked song. Hold down Shift key and select it. That selects all songs in your music library that are currently checked. Drag the selection to your new "iPad Songs" playlist, OR right-click selection and Add to Playlist... You now have a playlist with all of your currently checked songs.

Then, use the suggestion above to set iTunes to automatically sync that playlist to iPod (instead of syncing all checked songs). Going forward, manage that playlist (add and remove songs) in your iTunes library, instead of scrolling through your list of 9000 songs to check and uncheck songs. iTunes keeps your iPad updated with the same changes. You can leave all songs checked.

I am having the same issue, after updating from iTunes 11 to 12.3 All songs that were bought through the iTunes store. Even songs that i try to "hide" magically reappear. Quite frustrating.

This is in response to the solutions provided by K. Watanabe. While I don't doubt that creating a separate playlist for your various devices will work, this is a ridiculous and tedious amount of work and should be unnecessary. It continues to be very troubling that each update to iTunes or iPod software introduces serious user problems that were never there previously. My iPod became effectively useless in my car with a prior update. That problem took months to resolve with one of the latest updates. Now my iTunes mysteriously checks songs that were dutifully unchecked for a variety of reasons. Users spend a lot of time customizing their iTunes libraries so that it works for them. Checking and unchecking songs is the least of such customizations. I have some classical collections with 50-100 tunes. I don't necessarily want the entirety of those collections on my iPod or iPhone. So I check the ones I want and uncheck the ones I don't want. This takes a great deal of time when customizing an entire music library. Suddenly, everything is undone with an update. C'mon Apple - fix this.

Even now, my iPod has a periodic relapse where it shows "All Music" even though I continue to reset it to display only the downloaded music. It does me no good to download 8 songs to my iPod from a 50 song collection in my library (eg, Chopin collection) only to have the iPod display all 50. Of course, this problem is exacerbated when, instead of just showing the 42 non-downloaded songs, it actually rechecks all 50 and downloads all 50 with the next sync.

I suggest that those who are experiencing the mystery "checking" problem, contact Apple directly. Then maybe they will fix it 6 months from now.

All in this Forum post, and particularly Williasp, I agree completely! I manage my original iPod touch (still running on iOS 4.2.1) by using checks. Everything that I do not want on the iPod touch (which rides in the car) is unchecked. I use the Sync only checked music on the Summary tab to control. I too have been finding everything is rechecked, and I too can confirm that it is purchased from iTunes Store music. I did have Apple Music for the three month trial, but I did not continue with it so I should not have any connection still in that vein.

It is frustrating. Walt Mossberg wrote a recent editorial about the decline in Apple's "It just works" ecosystem...basically since Steve Jobs' passing, and how bloated iTunes software has become, not to mention the messed up Music app on iOS.

Thank you for all posting this issue. I thought I was losing my mind.

Last question: Has anyone tried re-building their iTunes libraries to see if that stops the checking/unchecking issue? I'm reluctant to do it as I've read is resets your Date Added columns to the day of rebuilding...destroying that piece of information. I can't confirm, but was curious to ask.

I can't say for certain that iTunes isn't doing something wrong, but it is possible to inadvertently alter checked status. Cmd-clicking a checkbox will tick or untick all boxes in the current view.

Given the ability to accidentally check or uncheck all songs, and also the fact that unchecked songs are skipped during normal playback, I don't recommend using checkboxes as a sync control mechanism. Much better to make a playlist of the songs that you want on your device, or those that you don't plus a smart playlist that works out what to sync.

tt2

turingtest2: The issue of unchecked songs mysteriously becoming rechecked is real and not accidental. It is not occurring through a careless keystroke. When I check or uncheck a song, I actually click on the box next to the song I want to uncheck. It's pretty simple and failsafe. At most, one might accidentally click the song above or below. I generally don't make wholesale changes. Also, most of the songs that were unchecked have been unchecked for months or years. So it is quite clear that a recent change in iTunes has caused the system to suddenly begin checking songs purchased via iTunes (as opposed to CD conversions that remain as is).

And, as I said before, it would be extraordinarily tedious to create special playlists for each device. Plus, if you create a playlist, you simply get a list of songs and I like to view my collection by artist. I want all of my Chopin under Chopin. I don't want a Ballade at one end of the song alphabet and a Prelude at the other end. (OK, I appreciate one can probably spend even more time creating the playlist to arrange it the way you want it.)

All of this should be unnecessary. Updates shouldn't screw up simple things like this that are fundamental to usability. If you want to annoy your customers, this is a great way to do it.