My 5th gen iPod no longer plays songs that I bought from iTunes

After updating my iPod's software, the setting on it were erased so that everything was in sync with the computer. Not realizing this I found that all of the music on my iPod had to be re-uploaded onto my iPod. However the music and videos that I purchased no longer play despite being listed on the iPod. Can someone please help I've run out of options.

See this...
iPod does not play content purchased from the iTunes Store
Post back if the problem persists.
btabz

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My iphone wont let me play songs that I bought from iTunes. It says "The requested URL was not found on this server" How can i play my music also my music videos again?

I bought a few songs and music videos from iTunes, then all of a sudden it wouldn't play and would just skip to the next song. With the music videos it would do the same. Also, this message would show up " The Requested URL could not be found on this server" What does that exactly mean? And what do I need to do to play my music/videos again?

This previous discussion has a solution:
https://discussions.apple.com/message/16527576#16527576

After installing the latest of iTunes the original files for almost 300 songs cannot be found for syncing to my iPod. The files are songs that were bought from iTunes, and copied into iTunes from CDs.

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Apparently, security programs like Macafee and Norton view Itunes updates as new programs and block then from access. If you add Itunes to the list of exemptions, it solves the problem.

My iphone wont play certain songs that i bought from itunes on my phone, it just skips songs. Does anyone know how to fix this?

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HT1386 My I phone used to play music that I had downloaded from Cds to my computer, but since the last update,my phone only plays songs that I bought on itunes. It still shows I have all my old music but won't play any of it. What's going on?

Ok, so I synched my iphone 4 to my computer recently and now when I go to play music on my phone, only the songs I've bought on Itunes play. I put all of my music collection that is in CD form on my computer and it used to play on my phone too, but now it just skips those songs. They still play on my computer though. I've been trying to figure out what the problem is for over three days or so and am about to loose my friggin mind! Can anyone help me?

De-sync all your music to remove it from the device, then restart (hold down the home button along with the sleep/wake button until you see the apple, then let go). Now re-sync your music.

Songs that I bought from ITunes and play on my computer, will not upload to my IPhone because it says they are not authorized even though they are. How do I fix this?

These songs were fine when I originally bought them, they play on my computer, and even played on my old Iphone. I have deauthorized and authorised my computer serval times, but nothing seems to fix it. What do I do?

Like this:

My old computer recently broke. It was a macbook. Now i am trying to transfer all my music from my ipod to this new comp which is a PC, but its only letting me transfer the songs that i bought from Itunes. How transfer all my music across to this new comp

my old computer had recently broken down and my itunes librrary was on it. Thankfully i had all my music on my ipod. Now i have a new PC computer and id like to transfer all of my music onto a new library on this computer.The problem is its only letting me transfer all the purchased songs from my ipod,not my whole library,otherwise it will wipe all the music from it. How do i sync my whole library from my ipod to this new itunes?

You need a third-party program lke one of those discussed here:
newer copy

5th Gen iPod Unable To Play Purchased Videos & Music

Hi!
Sometimes it's a mistake to update the iPod just before a trip! So I found out as my 5th Gen iPod would not play any of the purchased videos or music I had on it. All of the other music on the iPod played fine and so, too, did my own iMovie videos, so I knew that nothing was really that wrong with the iPod. It just wouldn't play the purchased stuff. Yeah... that's right, the music and videos that came with DRM protection wouldn't play! If it's on my iPod, wouldn't it have been legally downloaded in the first place? Here is the set up: I changed the setting on my computer to allow it to sleep. I then had some problems so I changed it back to never sleeping. One problem was with iTunes. My iTunes would not play my purchased stuff because somehow, my computer "forgot" that it was "authorized" and gave me a message stating that I had to re-authorize the computer. I did so even though I knew that it was already authorized. But.. according to the message I got after that, I now had 1 computer authorized of my allowed five. Weird... but "okay"... I thought... "everything is working, again." But around then, I had updated my iPod and then went out of town for six days, only to find that the purchased videos and music would not play. Oh... like my iPod was not "authorized!" Okay.. This is infuriating as really this DRM restriction software ends up impacting negatively the honest people far more than any fans of the old Napster. This is a fact Apple well understands and the music industry seems oblivious of. So... despite the fact that I have legally downloaded and paid for every piece of music and video I have on the computer and iPod, I am treated like the scum of the earth by having my purchases not work on my iPod because my computer forgets it is authorized! But you know, I am a bright thing and solved my own problem. I thought resetting the iPod would solve the problem but it did not. I re-synced the iPod when I got home, after making sure the computer was still authorized, but this too failed to solve the problem. What did solve the problem was deleteing one of the TV shows and then re-dragging it on to the iPod (I have it manually managed) and syncing the iPod, again. Suddenly all of the purchased videos and music work again. We are back to happy times with the iPod again. But I must ask, who are you really hurting with this silly DRM thing, anyway?

There has got to be a better solution to this problem, which I have as well, than the ones suggested above (no offense). So I'm bumping the post and praying someone can help me out. I'm using iMovie 4.0.1 and iTunes 6.0.1.
Unforunately for all of us, there is not.
Sue
BTW-no offense taken.

My iPod is not playing the songs that I purchased from iTunes.

My iPod is not playing the songs that I purchased from iTunes.

Empty/corrupt library after upgrade/crash
Hopefully it's not been too long since you last upgraded iTunes, in fact if you get an empty/incomplete library immediately after upgrading then with the following steps you shouldn't lose a thing or need to do any further housekeeping. Note that in iTunes 11 an "empty" library may show your past purchases with links to stream or download them.
In the Previous iTunes Libraries folder should be a number of dated iTunes Library files. Take the most recent of these and copy it into the iTunes folder. Rename iTunes Library.itl as iTunes Library (Corrupt).itl and then rename the restored file as iTunes Library.itl. Start iTunes. Should all be good, bar any recent additions to or deletions from your library.
See iTunes Folder Watch for a tool to catch up with any changes since the backup file was created.
When you get it all working make a backup!
Should you be in the unfortunate position where you are no longer able to access your original library, or a backup of it, then see Recover your iTunes library from your iPod or iOS device.
tt2

Finally got my 5th gen. ipod working and when i hook it up to itunes it....

finally got my 5th gen. ipod working and when i hook it up to itunes it says "iTunes cannot read the contents of the iPod “IPOD”. Use the iPod Software Updater application to restore the iPod to factory settings." i put in the cd after this and it didnt do a thing. i really have no idea what this means. please help.

finally got my 5th gen. ipod working and when i hook
it up to itunes it says "iTunes cannot read the
contents of the iPod “IPOD”. Use the iPod Software
Updater application to restore the iPod to factory
settings." i put in the cd after this and it didnt do
a thing. i really have no idea what this means.
please help.
I had this problem, then replaced my usb pci card w/ a new one and it worked...

I updated my iPod and it erased everything i had on it. How do i retrieve the songs that i bought from the iTunes store? when i try to download/buy them again they tell me i have already purchased them do i want to buy them again?

I updated my iPod and it erased everything i had on it. How do i retrieve the songs that i bought from the iTunes store? when i try to download/buy them again they tell me i have already purchased them do i want to buy them again? I have authorized my computer but none of them are in my music now.

You buy one and only one download.
It is your responsibility to move/copy/backup your music.
Certainly you did not update your ipod without making sure that you had transferred anything purchased on the ipod to your computer and included it in your regular backup copy of your computer.

My iTunes will no longer play videos/music videos (bought from the iTunes store) since the last update? (Win7 64bit)

My iTunes will no longer play videos/music videos (bought from the iTunes store) since the last update? (Win7 64bit)

Guys I have the same problem.
Since I installed iTunes 10.5 I can't play any of my music videos downloaded from the iTunes store.
I can play music ok but no videos. I just click on the videos and nothing happens!!
Help..... is there a remedy???

When I switched computers my songs now cut off and don't play out. How can I get my songs back to play fully that I purchased from ITunes over the past years?

When I switched computers my songs now cut off and don't play out. How can I get my songs back to play fully that I purchased from ITunes over the past years?

Other people have been having similar problems with songs over the last few days, I assume that there has been a problem with Apple's servers.
Depending upon what country that you are in (music can't be re-downloaded in all countries) then try deleting those tracks from your iTunes library and redownload them via the Purchased link under Quick Links on the right-hand side of the iTunes store home page on your computer's iTunes : re-downloading.
If you aren't in a country where you can re-download music or if they re-download in the same state then try the 'report a problem' link from your purchase history : log into your account on your computer's iTunes via Store > View My Account and you should then see a Purchase History section with a 'see all' link to the right of it ; click on that and you should see a list of your purchases ; find those songs and use the 'Report a Problem' link.

HT203167 I have a few songs that I purchased from iTunes store that now only play the first 2 or 3 words of the song. How do I get the whole song back?

I have a few songs that I purchased from iTunes store that now only play the first 2 or 3 words of the song. How do I get the whole song back?

Hello hmcc44,
You may need to delete the items from your iTunes Library, then redownload them.
Deleting files from the iTunes library and your computer
http://support.apple.com/kb/HT3842
Downloading past purchases from the App Store, iBookstore, and iTunes Store
http://support.apple.com/kb/HT2519
If the issue persists beyond that point, I would recommend reporting an issue with the tracks to the iTunes Store.
How to report an issue with your iTunes Store, App Store, Mac App Store, or iBookstore purchase
http://support.apple.com/kb/HT1933
Cheers,
Allen

So i just got a new mac, and i am trying to sync my songs that i bought on itunes, and some of the worked, but a huge selection of them have a little exclamation mark beside it and it says it can't be downloaded, why?

so i just got a new mac, and i am trying to sync my songs that i bought on itunes, and some of the worked, but a huge selection of them have a little exclamation mark beside it and it says it can't be downloaded, why?

Hello Pork Chop 2,
Congratulations on your new Mac! It sounds like your purchased songs are not playing completely after you downloaded them. I recommend to following steps for an issue like this:
Symptoms
Occasionally, if a song purchased from the iTunes Store on a Mac or PC was not downloaded completely, the song may not play back fully. The song may abruptly stop during playback, and iTunes may start playing the next song in your library or playlist.
Resolution
If iTunes in the Cloud is available in your country, try the following steps to resolve the issue:
Delete the purchased song that is exhibiting the problem from your iTunes library.
Click on the Purchased link in the iTunes Store to view your previously purchased music.
Download your previously purchased song from this list.
You can find the full article here:
Songs in iTunes may not play back completely
http://support.apple.com/kb/TS4357
Thank you for using Apple Support Communities.
Best,
Sheila M.

My 5th gen iPod no longer plays songs that I bought from iTunes

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