Basically, when you buy music from iTunes, it comes with a copyright protection called DRM. These DRM-protected songs are locked so that they only work with Apple MP3 players. That means that if you bought a Microsoft Zune, you cannot use iTunes music.

So, what is the solution? You have to burn a CD. When you do this, the DRM is removed (because the music is converted to a non-DRM-compatible media). After you burn the CD, you can rip it to your PC as an MP3 file which no longer has DRM.

1. Insert a CD-R or CD-RW disc into your CD-ROM drive.
2. Burn your playlist to make an "Audio CD". You cannot select the "MP3 CD" option since it requires the DRM protected iTunes music files be converted to (DRM free) MP3.
3. After the audio CD is successfully burned, insert the disc into your CD-ROM drive again. Then you can use iTunes to import the music tracks on the burned disc as MP3 files.

Alternatively, you can use TuneClone. TuneClone makes a virtual CD-ROM drive, tricking your PC into believing that you are burning a CD. Therefore, the DRM is removed without wasting a CD. Below is the step by step tutorial using TuneClone and iTunes 9.0.2 to convert M4P to MP3.

Step 1. Download and install TuneClone

TuneClone is compatible with Windows XP, Windows Vista (except Vista 64 bit) and Mac OS X 10.5 or above.

(Windows Version | Mac Version)

Step 2. Create a new playlist in iTunes

Create a new playlist, and add the iTunes songs you want to convert to the playlist.

Step 3. Make burning settings in iTunes

Right click the playlist you just created and choose "Burn Playlist to Disc". Or you can select part of songs from the playlist and click the "Burn Disc" at the bottom right corner of iTunes interface. In the pop-up dialog of "Burn Settings", make the settings as highlighted below:

Step 4. Start burning

Click the "Burn" button to start burning. After the burning gets started, TuneClone will automatically convert the iTunes music to MP3 files. You can open the manager screen to show all the converted music files.

Tip: The most important step is to choose the CD burner. Then TuneClone Audio Converter will convert the music files automatically. It is exceedingly easy when you want to batch convert lots of files.

The detailed tutorial for Windows is available at: http://www.tuneclone.com/use-tuneclone-in-itunes9-convert-m4p-to-mp3.php
The detailed tutorial for Mac is available at: http://mac.tuneclone.com/how-to-convert-m4p-to-mp3-on-mac.php

The following article will share with you four ways of removing DRM protection from iTunes music on Mac OS X. You can choose your favorite method to help you convert iTunes M4P music to MP3 or (DRM free) AAC format for playback on MP3 Player, MP4 Player, Mobile Phone Player, etc.

Method 1. Remove DRM from iTunes music with burning-and-ripping method

1. Insert a CD-R or CD-RW disc into your CD-ROM drive

2. Run iTunes, create a new playlist and burn it to make an “Audio CD”

3. After the Audio CD is successfully burned, insert the disc into your CD-ROM drive again. Then you can use iTunes to import the music tracks on the burned disc as whatever format (MP3, AAC, etc) you selected in iTunes preferences for importing.

Method 2. Remove DRM from iTunes music with Virtual CD Burner

You will need to download TuneClone Audio Converter for Mac first. Run this DRM Removal Software and it will let you install a virtual CD burner, which will be used to convert iTunes music files.

Run iTunes, create a new playlist and add the DRM protected iTunes songs to the playlist.

Right click this playlist and choose “Burn Playlist to Disc”. Alternatively, you can click the “Burn Disc” button at the lower right corner of iTunes interface.

In the pop-up dialog of “Burn Settings”, select “CDWriter TuneClone” as default CD Burner, choose “Audio CD” as Disc Format and tick “Include CD Text” ( to perserve the music metadata such as name, artist, album names ).

Tip: You can easily get the output MP3 files on your Mac machine by clicking the “Reveal in Finder” button on the manager screen.

Method 3. Remove DRM from iTunes music with iMovie ‘09

Run iMovie and create a New Project. In the iMovie window, select the ‘Music’ tab. You will notice that the top right portion of the interface now offers a media browser. Locate the playlist which contains purchased music, or search by artist/title.

Select the DRM-laden song and drag the file from the media browser into the iMovie timeline.

In order to export the song, iMovie requires that a visual image be associated with the audio track - iMovie thinks that it is going to be exporting a movie. Simply drag a blank image (or any other image) to the track above the previously imported audio file. Once iMovie has processed the image, select the ‘Export using QuickTime…’ sub menu item from found inside ‘Share’ in iMovie’s menu bar.

In the Save as… dialogue, select “Sound to AIFF” in the Export drop-down menu, Choose an appropriate directory for iMovie to export to, title the file, and select ‘Save’.

Locate the exported AIFF audio file and drag to your iTunes Library. Right-click on the file and select “Create MP3 Version”. Once completed, ‘Get Info’ on the new file, edit meta data, add album art, and trash the originally purchased and AIFF audio files from your iTunes library.

Method 4. Remove DRM from iTunes music with FairGame

FairGame is freeware to remove DRM protection from iTunes music on Mac OS X. It will convert the DRMed songs you bought on the iTunes Store to an unprotected format (using iTunes default encoder) and keep all the original metadata, lyrics and artwork. FairGame doesn’t do lossless DRM stripping. It re-encodes protected AAC files purchased in iTMS into unprotected AAC file using Apple’s iMovie software.

What you MUST DO (only once) to get FairGame to work:

enable “Access for assistive devices” in the “Universal Access” system preference

select “Place clip in Movie Timeline” in the “Import” preference of iMovie HD

Then you can simply:

select some songs in iTunes

click on the “Process songs” button

Don’t touch anything and wait until it’s done…(FairGame is scripting iMovie’s interface to process the songs, don’t interfere)

iTunes doesn't allow users to burn iTunes movies or TV shows to DVD directly. If you want to burn movies or TV shows downloaded from iTunes store on to a DVD for playback on your DVD player or backup iTunes movies and TV shows to DVD discs, you'll need to get a DRM removal tool to remove the iTunes Digital Rights Management (DRM) license protection first and then find a DVD authoring program to convert the DRM free Video to DVD format for burning to DVD.

The only tool you need is Media Converter Ultimate (Free Download), which combines into one prgram the functions of DRM Removal, DVD Creator, DVD Ripper, Media Converter, Media Transfer, etc.

The following step by step guide will share with you how to remove DRM from iTunes M4V movies and TV shows to burn iTunes M4V to DVD for backup, enhancement or playback on traditional TV sets, home DVD players with Media Converter Ultimate .

Step 1. Remove DRM from iTunes movies and TV shows

Click the "Add" button to load iTunes media. iTunes movies and TV shows are usually located in the Movies and TV Shows folders under *:\My Documents\My music\iTunes\iTunes Music. After making some necessary settings, click the "Start" button to begin the conversion.

Step 2. Burn iTunes movies and TV shows to DVD

After the conversion, there is a pop-up dialog asking you to either "Burn to DVD" or "Copy to Devices" (media transfer). Choose the former and a window will pop up, with the (DRM free) files you just converted listed ready to be burnt.

Click "OK" to go to the next "Burn to DVD" window, where you can choose a menu template, set background image/music, etc for the output.

Click "Next" to make further DVD burning settings. You can choose to burn to DVD drive (insert a DVD disc first), burn to ISO file or burn to DVD folder. You can also specify the output path for the ISO file or DVD folder, choose TV Stardand (NTSC or PAL), Aspect Ratio, etc for the output. Besides, the software will estimate result file volume for you. Click "Start" and the whole DVD burning progress gets started.

The burning status will be clearly shown in the progress bar. After the whole burning process, you can get the output file and start to enjoy your favorite iTunes movies and TV shows on a DVD player.

Extracted from http://www.softdiggs.com/howto/burn-itunes-m4v-movies-tv-shows-to-dvd.php

"My laptop HDD recently failed, so I replaced it with an iMac. Fortunately, my iTunes library was on an external HDD, so I have copied it across to the iMac. However, the songs that I have purchased from iTunes do not seem to be available. They have copied across, but are 'greyed out'. I have authorised my new computer to play purchases. Is there anything else I am forgetting?"

It is relatively painless to switch over from Windows to Mac as Mac has support for a lot of commonly used files like Microsoft Word documents, Powerpoint slideshows and Adobe PDF files. So, compatibility is hardly an issue. What you do have to take note of however while switching over to Mac are your iTunes library and WMAs. Note: This tutorial was written under the assumption that you are running the latest version of iTunes ( iTunes 8 ) on both your Windows and Mac.

1. Add WMAs to iTunes on Windows

iTunes for Windows is built with Windows Media Audio (WMA) support - it is able to play and convert WMAs. However, because WMA is a proprietary codec, it isn't available in iTunes for Mac. If you're not careful, you'll be left with a lot of WMAs which will be unplayable on your Mac.

The easiest way to dodge this problem is to convert all the WMAs you have while you're still on your Windows machine. In your iTunes General preferences, under 'Import settings', make sure to have AAC or MP3 selected. Configure the bit rate if you like but because you will be converting from one lossy codec to another, there's bound to be a profound loss in quality.

However, if the WMAs are DRM protected, it will be a little bit difficult. One method of dealing with the DRM protected WMAs is to get an audio converter. Make a simple Google search and you will get a lot of converters that can convert WMA to MP3. However, those that can convert DRM protected WMA to MP3 are rather limited. The one that attracts my attention is TuneClone Audio Converter (fow Windows only), which isn't free but very well worth a shot if you have lots of DRM protected WMAs ready to be switched to Mac. TuneClone Audio Converter is capable of removing DRM protection from WMA files and convert WMA to iTunes (both Windows and Mac) compatible MP3 format by installing a virtual CD burner. Here is the guide: http://www.tuneclone.com/how-to-convert-wma-to-mp3-for-ipod.php

Apart from that, TuneClone Audio Converter can also be used to convert iTunes M4P (protected AAC) to MP3 for non-Apple MP3 devices. Here is the guide: http://www.tuneclone.com/itunes8-m4p-to-mp3.php

After getting the protected WMAs converted to MP3, add to your iTunes library the MP3 files, which will be transferred to Mac along with all the music in iTunes library.

2. Backup iTunes library on Windows

In Windows, open iTunes. Consolidate your library from the 'File -> Library' menu.

This will move all the music files into the iTunes Music folder and sort them by artist and album.

Navigate to your My Music folder. It's typically found at C:\Documents and Settings\~username~\My Documents\My Music.

Copy the iTunes folder to the Desktop of your new Mac. Depending on the size of your library and the method of transfer, this could take a while.

3. Organize iTunes on Mac

If you are running iTunes on your Mac for the first time, you'll be prompted with the initial welcome setup procedure. When it asks to search your drive for music files, make sure to decline. At the end, you'll be presented with a fresh, empty iTunes library. Now, quit iTunes. By default, it would have already set up its own iTunes Music folder located in ~/Music. Go over to this location and delete the iTunes folder then copy and paste your iTunes Music folder from the desktop into it (the one which you have just brought over from your Windows computer). After all this is done, launch iTunes and you'll be rewarded with your old, personalized iTunes library.

This guide is going to show you how to remove DRM protection from iTunes music, convert DRM protected iTunes M4P to MP3, M4A to MP3, AAC to MP3 and transfer iTunes music to Zune HD. First, let’s take a look at the video/audio formats Zune HD accepts:

Video Support:
WMV
MPEG-4 (MP4/M4V) (.mp4) Part 2 video
H.264 video
DVR-MS

Audio Support:
Windows Media? Audio Standard (WMA) (.wma)
WMA Lossless
Advanced Audio Coding (AAC) (.mp4, .m4a, .m4b, .mov): .m4a and .m4b files without FairPlay DRM
MP3 (.mp3)

So, if you want to play DRM protected iTunes M4P, M4A, AAC music on your Zune HD, you just need to use TuneClone Audio Converter to convert the iTunes music to MP3 format and then transfer the output MP3 to your Zune HD.

Now let’s take a look at how it performs to convert the iTunes music to MP3 format for Zune HD using TuneClone Audio Converter:

1. Create a new playlist in iTunes.

2. Add the iTunes songs to the playlist.

3. Launch TuneClone Audio Converter. Click the “Settings” tab. In the pop-up window, you can specify output folder, output file name format, output format, etc for the output files. Note: You can check whether TuneClone virtual CD drive is successfully installed and where it is installed at the bottom left corner of the interface.

4. Switch to iTunes. In iTunes, select the playlist you just created and click the “Burn Disc” button.

5. In the pop-up window of “Burn Settings”, select “TuneClon Virtual_CD-RW” from the “CD Burner” drop-down list, click the radio button next to “Audio CD” and tick “Include CD Text” option. Click “Burn” to start burning.

6. Upon the completion of burning the disc and encoding the music, you can open the TuneClone manager screen to show all the converted music files. To locate the output folder, simply click the “Folder” tab on the interface.

7. After you get the output music files, connect your Zune HD to computer via the USB cable, drag and drop the converted MP3 files to the Zune Software, then you can sync the iTunes M4P music to Zune HD with the help of Zune Software at ease.

Extracted from http://www.tuneclone.com/transfer-itunes-music-to-zune-hd.php