iTunes has been around since January 2001, before even the iPod launched. The software used to be fundamental when it came to syncing music with that device, and later on, syncing and updating the iPhone, but now-a-days iTunes is of less importance as many iPhone and iPad users choose to sync their music via the cloud. A good thing too, because iTunes isn’t without it’s problems and if you do choose to use the software to update the software on your iPhone, or sync your music, it’s likely that you have experienced one or two of the issues we will examine below.

If you are using iTunes on your Mac as a jukebox – which is what it was always intended to be before it became the centre of everything iPhone related – you’ll also no doubt have run into a few problems. Especially if you have signed up for any of the services that run alongside it, such as Apple Music and iTunes Match.

Of course, there is still more to iTunes than music – you can also store movies and TV series there, used to keep a back up of your Apps too.

If the complexities of iTunes have you confused, if something in particular has you stumped, or if you iTunes library is just not playing right, we may have discovered some fixes. If you can’t find the answer below be sure to let us know in the comments below and we will attempt to answer it in a later revision of this article.

Click on the links above to get to the section most likely to be relevant to your problem:

Updating iTunes on your Mac

Keeping your iTunes software up-to-date on your Mac (or PC) can avoid many of the questions we address below. It can also be a challenge in itself. First we will look at what to do if your iTunes won’t update.

Can’t install or update iTunes

From time to time Apple updates iTunes, and when it does you can guarantee that some people will encounter difficulties updating the software.

One reason you might not be able to update iTunes is if there is a problem with the settings on your Mac (or PC) that stop it being able to access Apple’s software update server. If the latter is the issue then you may see a message stipulating: ’This device isn‘t eligible for the requested build‘ – this is the error you will get if iTunes can’t communicate with Apple’s software update server. If that’s the case, Apple outlines the fix here.

Is iTunes down or not working?

From time to time there are issues when the iTunes Store goes offline due to issues with Apple’s server. Find out if this is the case here.

Syncing an iPhone with iTunes

This is a common issue, perhaps because it’s often the case that you are being asked to sync your iPhone with iTunes because there is a problem with your iPhone. We look at a couple of scenarios below.

iPhone not recognised by iTunes

If you plug your iPhone into your Mac (or PC) and nothing happens Apple’s advice is that you should start by updating iTunes on your Mac (it’s also worth checking to see if there are any other software updates required). Then force restart your iPhone before connecting it to your computer via USB (here’s how to force restart an iPhone).

If during the process you see a Trust this Computer alert, make sure you tap Trust to unlock your device and enter your passcode.

If you are still having problems it’s worth trying a different USB port, a different UBS cable, and failing that, another computer.

And if even that doesn’t solve the problem, try holding down the Option;/Alt key, click the Apple menu, and choose System Information or System Report. Then, from the list on the left, select USB. If you see your iPhone, iPad, or iPod under USB Device Tree, you may need to uninstall third-party security software. If it’s not there, you should contact Apple Support.

If you were reacting to an error message on your iPhone that told you to Connect to iTunes, read: How to fix ‘iPhone is disabled. Connect to iTunes’ error messages.

iPhone won’t sync with iTunes

If you have an extensive collection of music on your Mac that you want to appear on your iPhone (and you don’t pay for iTunes Match,) you will need to sync your iPhone and iTunes on your Mac in order to copy the music to the iPhone (or iPad).

Unfortunately this is an other area where sometimes you may encounter issues. If your iTunes won’t sync songs to your iPhone or iPad read on:

First things first, in order to sync your iPhone with iTunes (if you don’t sync via the cloud) you need to plug in your iPhone or iPad into your Mac via USB and open iTunes. Once connected you should see an icon for your iPhone or iPad appear at the top of the iTunes window. If you don’t see that icon, you should follow the advice in the iPhone not recognised in iTunes above.

One reason why your iPhone or iPad might not sync via iTunes is if you use iCloud or other services like Apple Music to keep your content up to date across all of your devices – in that case syncing through iTunes might be disabled.

Beware: if a track is on your iPhone but not in the music library on your Mac you will lose it when you sync your iPhone with iTunes unless you use a service like iTunes Match.

Another reason why your iPhone, iPad or iPod won’t sync with iTunes is if there is a file on your computer or iOS device that is locked. In this case, try syncing only a small amount of content at a time, adding more content until you see the error message. That way you can identify the content that is causing the issue and delete and re-download it if necessary.

For more advice on this issue we have this article: How to make iTunes recognise an iPod, iPhone or iPad.

Music won’t play in iTunes

There are a few reasons why music might not play in iTunes. Sometimes it will be due to copy-right issues, whereby you need to prove you own the track in question, other times it might be that the track is no longer correctly linked to your iTunes library. We look at issues with music not playing below:

How to authorise Mac

Sometimes you might try and play a track only too see a message that your computer is not authorized to play it.

It’s possible that you had copied a track from someone else and therefore it’s tied to their Apple account (and you should get your own copy, obviously), but if you do own the track it could be that somehow your computer has become de-authorised. This could be because you have authorised another device which has taken you over the five computers limit.

To authorise your computer to play tracks in iTunes (and any other content you have purchased from the iTunes Store, including movies and audiobooks) start by opening iTunes (if it’s not already open).

  1. Click on Account.
  2. Click on Authorisations and Authorise this computer.
  3. Enter your Apple ID and Password.

If you have reached the limit of five computers you can de-authorise all your computers the same way.

  1. Click on Account.
  2. Click on Authorisations and De-authorise this computer.

What if you have old Macs that you no longer use, but they are chipping into your allocation as they are still authorised?

  1. Go to Account > View my Account.
  2. Scroll down and beside Computer Authorisations you will see how many computers are authorised, and a button to Deauthorise All.
  3. You need to de-authorise all the computers before you can reauthorise the ones you want to continue to use iTunes on.

Some tracks are greyed out in iTunes

There are a few reasons why tracks might be greyed out and unable to play in iTunes.

It could be because they have become corrupted when you were syncing the iPhone with your computer. In that case the best option is to delete them and re-download those tracks.

Another possibility is that you use Apple Music and somehow your music library has got out of sync. In which case:

  1. Log out Tunes: click on Account > Sign Out.
  2. Quit iTunes.
  3. Launch iTunes and login to iTunes again.

A related issue is when exclamation marks appear in iTunes, we have look at How to get rid of exclamation marks in iTunes here. Generally if you see an explanation mark next to a track in iTunes it means that iTunes cannot locate the track.

Apple Music won’t play in iTunes

If you subscribe to Apple Music you will be able to play any track in the Apple Music library.

Sometimes if you really like a track in Apple Music you might download it so that you can play it on your Mac at any time. If you later find you can’t play the track there are a few potential causes for this.

It is possible that Apple no longer has the rights to play that track in Apple Music. If that’s the case you will need to find another way to get hold of the track. It’s possible that it is still available to download from the iTunes Music Store, just not available to Apple Music subscribers who are essentially just renting the track which means it can disappear at any time.

Problems adding music to iTunes

There are various ways in which you can add music to iTunes, including simply downloading from the iTunes Store. You can also import old iTunes libraries or copy tracks over from USB backups. We discuss how below.

How to rip CDs if you don’t have an optical drive

Importing music to your iTunes library from the pile of CDs in your loft might sound like a great idea. But what if you don’t have an optical drive on your Mac.

Since Apple stopped launching Macs with optical drives some years ago this is a very likely scenario. There are a couple of ways in which you can import music from a CD though.

One way is to plug in an optical drive such as Apple’s SuperDrive (more information about that, and some alternatives, here: The best Mac compatible DVD-R drives you can get.

You can also use a second Mac or PC with an optical drive to rip CDs and get them into the iTunes library on your Mac that doesn’t have a drive. We explain how to rip CDs if you don’t have an optical drive here.

How to merge multiple iTunes libraries

What if over the years you have ended up with multiple iTunes Music libraries spread across various hard drives and Macs. Perhaps in the past you have backed up an old library because you were running out of room, or maybe you accidentally stared a new iTunes library, or created a new library when you got a new Mac. You may also have separate iTunes libraries running on various Macs – a different one at home to the one at work. What if you decide you want to listen to some of your old tracks?

One way to do this is to manually drag and drop your music folders into your newer iTunes window. The only issue is might end up with quite a few dulipcates – especially if your current iTunes library still has some of the older tracks in it.

You could use Apple’s own duplicate identifying tool in iTunes to locate the tracks, but there is third-party software that can make the process much easier. We have an article about how to remove duplicate tracks here:

The other downside to combining multiple iTunes libraries is that you’ll lose play counts, last played dates, ratings, and playlists.

How to buy music if you subscribe to Apple Music

Buying music via the iTunes Music Store is easy, but it’s not obvious how to do so if you have a subscription to Apple Music.

Obviously you dint have to buy the track as you can simply download the Apple Music track to your iTunes library, but if you want to make sure you have it should you decided not to continue your Apple Music subscription (or if the music disappears from Apple Music) you may want to ensure you own it outright.

  1. Right-click on the track you wish to buy and you’ll see a contextual menu.
  2. Choose Go To > Song in iTunes Store.

(This doesn’t work in iOS, only in iTunes).

We have more information on iTunes Match and Apple Music here.

How to get back missing music that has disappeared

Luckily if you have accidentally deleted a track that you had purchased from the iTunes Store, it’s quite easy to get it back.

Normally, when you choose Delete from Library, you’ll find the file in the Trash, so you can add it back to your iTunes library.

If that fails, it is possible to download previous purchases again without having to pay for them. We discuss how to recover missing iTunes music here.

If the reason you deleted the music from your library by accident is that you didn’t see the warning: “Are you sure you want to delete the selected song from your iTunes library” it may be because in the past you have ticked the “Do not ask me again” box.

If that’s the case, go to iTunes Preferences > Advanced > Reset all dialog warnings > Reset warnings.





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