The SuperSite Switcher Guide: From Mac OS X to Windows, iTunes Migration 101: iTunes to iTunes

If there's one thing that millions of Windows and Mac users have in common with each other, it's a shared experience with Apple's popular iPod portable media players and iTunes media management software. Both products work similarly between the Mac and Windows, offering identical or (in the case of iTunes) almost completely identical functionality.

Within the context of switching from the Mac to Windows, there are a number of ways to migrate over your music, videos, and other iTunes-based content. The simplest and most cost effective, of course, is to simply continue using iTunes and the iPod (and other related products, like Apple TV) with Windows. This is probably the approach most people will want, I'd imagine.

Thinking more radically, you can also choose to move your digital media libraries to more Windows-centric applications. For example, if you're an iTunes user but don't have an MP3 player of any kind, you may want to use Windows Media Player or the Zune PC software on Windows, both of which offer certain advantages over iTunes. Or, you may literally want to go all-in and replace your iPod (and, potentially, an Apple TV) with more Windows-friendly devices, such as the Zune.

I'll examine all three of these possibilities in this series. But the first step, regardless of how far you're willing to go into Windows, is to copy or move your existing media library from the Mac to Windows. So let's discuss that first.

Copying everything from the Mac

Apple's iTunes is available for free to users of both the Mac and Windows, and since the software is very similar between the two platforms, it's straightforward (if somewhat time consuming) moving content from one environment to the other. That said, there are some gotchas, and some things you're going to want to take care with.

Note: Have a USB-based hard drive handy, one that is big enough to store your entire media library. For maximum compatibility, it should be formatted with the FAT32 file system, which works in both Mac OS X and Windows.

Upgrade to the latest version of iTunes

Before doing anything else, make sure you're running the latest version of iTunes on both Mac and Windows. To do so, select Help and then Check for Updates in iTunes.

Consolidate your iTunes media library

iTunes manages music, of course, but if you're a power-user, you probably have a host of other content in there, including movies and TV shows, audio and video podcasts, audiobooks, iPhone and iPod applications, and iPhone ringtones. To get all of this content over to Windows, you'll want to first consolidate your iTunes media library and, ideally, back it up before going any further.

The consolidate step is important because it will put all of your iTunes-based media files into a single directory structure. For most Mac users, this won't be a huge issue, because the Mac version of iTunes places all content there by default. This is one of the big differences between the Mac and Windows versions of iTunes; during install on Windows, iTunes actually asks you if you'd like iTunes to organize your digital media content or whether you'd like to do that yourself. On the Mac, you're not given this choice, though you can manually prevent iTunes from organizing your content after the fact if you'd like.

To consolidate your library, open iTunes on the Mac and select Consolidate Library from the Advanced menu. A dialog will appear, explaining what's about to happen and noting that the process is not reversible. Click the Consolidate button to continue.

When the consolidation process is complete, you can view the results in your Music folder. You'll see an iTunes folder inside. Select it and tap Apple + I to display the Info window, which provides, among other things, the size (in GB) of the iTunes folder and, thus, of your complete media collection. This is a good time to back up the entire folder structure, ideally to a USB-based hard drive or similar.

Now it's time to perform some housekeeping tasks back in iTunes.

Export playlists

If you've spent a lot of time hand-crafting playlists in iTunes, you're going to want them over on the Windows side. Fortunately, Apple makes it easy to export your playlists, which you can then import on the Windows side, after a little editing.

Note: This process applies to normal playlists, and not Smart Playlists. I'll look at the latter in just a bit as well.

To export a playlist, select it in the Playlists list, right-click, and select Export Song List (or, choose Export from the File menu). iTunes will create a text file with the name of the playlist (makes sure to add a .txt extension to make it Windows-friendly). Save it to your desktop or another handy place, and then repeat for all of your (manual) playlists.

Secret: iTunes has an Export Library feature that exports all of your playlists to a single XML file. I happen to prefer working with text files, but you may be OK with XML. If that's the case, please feel free to use Export Library instead.

iTunes will let you export Smart Playlists, but when you import them on the Windows side, they'll be imported as manual (i.e. "dumb") playlists, not Smart Playlists, and they won't be automatically updated as are Smart Playlists. For this reason, you'll have to do a bit more work to get your Smart Playlists over. Here's how I do it. Right-click a Smart Playlist in the Playlists list and select Edit Smart Playlist. Then, take a screenshot of the window. The easiest way to do this in Mac OS X is to type Shift + Command Key + 4, make sure the Smart Playlist window is highlighted by the little crossbar cursor, tap the Space bar to select the window, and then click the mouse button. (Yes, it's really that convoluted to take a screenshot of a window in Mac OS X.) The screenshot will appear on the desktop; you might consider renaming it to match the name of the Smart Playlist. Repeat for all of your Smart Playlists.

Secret: There may be a better way to do this. I have't tested this yet as I'm on the road, but on the Mac version of iTunes, you can run an AppleScript called Export Smart Playlist Criteria v2.0 that could correctly import into the Windows version of iTunes. More info Doug's AppleScripts for iTunes

Export your ratings

If you've been a good iTunes user, you've spent a lot of time rating the songs in your music collection. There are many advantages to do this, especially for Smart Playlists and custom mix CDs. But while iTunes does make it easy to rate songs, it doesn't make it easy to export ratings. Fortunately, I have a trick to make this possible.

To export ratings, you will first need to create five Smart Playlists, one each for each rating, 1 through 5. To do so, select File, New Smart Playlist. Then, in the Smart Playlist dialog change the value for the first Rule drop-down from Artist to Rating. The second value will change to "Is," which is fine. And the third one will change to 5 stars. Change the third value to 1 star. Then, click OK and name the Smart Playlist as "1 Star" (or whatever). Repeat for 2, 3, 4, and 5 star rated songs. Then, export each Smart Playlist as described previously for manual (dumb) playlists, making sure to save them as text files with .txt (and not .xml) file extensions. In this case, the fact that we won't get a Smart Playlist on the other end isn't just OK. It's exactly what we want.

De-authorize iTunes Store and Audible account

If you are literally moving from the Mac to Windows, and will never use your Mac-based version of iTunes again, don't skip this step: You should deauthorize your Mac from your iTunes Store account and, if you're an audiobook user, your Audible account as well. Apple allows you to authorize up to five Macs and/or PCs with each iTunes Store account, and it is this authorization that allows you to play content purchased from Apple's online service. Audible has similar restrictions, where you can authorize up to 4 PCs/Macs and 4 portable devices. So if you won't be using the Mac-based iTunes library anymore, it makes sense to free up a slot in each. Obviously, if you'll continue to move between the environment, this step isn't necessary.

To deauthorize your iTunes Store account, select Deauthorize Computer from the Store menu. Then, in the Deauthorize Computer dialog, provide your iTunes Store account name and password.

To deauthorize your Audible account, select Deauthorize Audible Account from the Advanced menu. In the Deauthorize Audible Account dialog that appear, provide your Audible user name and password.

Copy everything to a USB hard drive

Now, you should copy (not move) everything to a USB hard drive. In this case, "everything" means the entire iTunes folder, any text- or XML-based playlist exports, and any Smart Playlists screenshots you may have taken.

OK, let's jump over to Windows and get all that content and other data imported correctly.

From iTunes Mac to iTunes Windows

Moving an iTunes library from the Mac to Windows is pretty straightforward. But even if you intend to eventually move to Windows Media Player or the Zune, you should first go to the trouble of duplicating your iTunes experience on Windows. That will make it easier to access your media collection from other applications later on.

Configuring iTunes on Windows

If you haven't installed iTunes on Windows yet, do so now. When prompted, uncheck the options "Keep iTunes Music folder organized" and "Copy files to the iTunes Music folder when adding to the library." If you've already installed iTunes, you can make this change by select Edit and then Preferences and navigating to the Advanced tab in iTunes Preferences. On the General sub-tab (you gotta love iTunes), you'll find these two options.

You can change these values after we're done configuring iTunes, by the way. In fact, you'll probably want to. But for now, it's important to make sure they're both unchecked.

Copy the iTunes content to the PC and import it

Now, open the Music folder and navigate inside of iTunes, iTunes Music. In a separate window, open the USB hard drive and navigate inside of iTunes, iTunes Music. Select all of the folders and copy them to the iTunes Music folder on the PC's hard drive.

When the library has been copied over, select all of the folders inside of iTunes Music (on the PC, not the USB hard drive) and drag them into the iTunes window. This will import the content into iTunes, a process that could take a while, depending on how large your library is. If you do have Audible content in there, you'll be prompted for your Audible credentials. Give iTunes time to import the music, analyze each music track, and perform other housekeeping tasks. It won't make a pronouncement when it's done per se, but the activity in the iTunes information bar, in the top center of the application, will eventually come to an end.

Edit playlists to match the Windows file path

If you do have any playlists, Smart Playlists, or ratings playlists to import, the trickiest part of your iTunes migration comes next. When you saved these playlists on the Mac side, they were saved with Mac-specific file paths, which look nothing like Windows files paths. So you'll have to manually edit each text file so that all of the old Mac file paths match your new Windows file paths.

Don't worry, this isn't rocket science. But be sure to work with a copy of your playlist text files, and not the only version just in case you mess something up.

Mac file paths will resemble the following:

[machinename]:Users:[username]:Music:iTunes Music

Meanwhile, Windows file paths will resemble this:

C:Users[username]MusiciTunesiTunes Music

What you need to do is open each playlist file in a text editor like Notepad (don't worry if it looks like a mess) and do a global search and replace. On my systems I need to replace the text:

Macbook:Users:paul:Music:iTunes Music

with this text:

C:UsersPaulMusiciTunesiTunes Music

To do this in Notepad, open one of the playlist files in Notepad and type CTRL + H to bring up the Replace dialog. Enter the appropriate file paths in the "Find what" and "Replace with" fields and then tap Replace All. Type CTRL +S to save the file and close Notepad. Then, repeat this process for each manual playlist.

Import playlists

Now it's time to import your playlists. To import a playlist, select File and then Import and navigate to the location you stored these files. Select a playlist and click Open. Repeat for each playlist.

Import Smart Playlists

Smart Playlists, of course, will require a bit more work. If you uses screenshots or otherwise documented your Smart Playlists on the Mac, you'll need to now manually recreate them on Windows. To recreate a Smart Playlist, select File and then New Playlist and enter the criteria for the Smart Playlist as noted in the screenshot. Then, save, name accordingly, and repeat for each Smart Playlist.

Import ratings

To get your ratings back, locate the 5 ratings playlists you made earlier and import them. As expected, each ratings playlist is imported as a normal (dumb) playlist, and not as a Smart Playlist. No problem.

Open the 1 Star playlist and select all of the songs it contains (CTRL + A). Then, right-click the song list and choose Rating and then 1 star from the pop-up menu that appears. Repeat this process for each playlist, changing the ratings to the proper value each time (songs in the 2 Stars playlist should be rated with 2 stars, and so on). Voila! Your ratings have been recovered.

Reconfigure iTunes

The final step is to consider changing those two options we discussed back at the beginning of this section back to their Apple-preferred defaults. If you're going to stick with iTunes on Windows, you'll most likely want iTunes to keep your content organized under the iTunes Music folder (i.e. "consolidated") and will want to copy future content into that folder when it's imported (rather than leave it in its original location). To make this changes, select Preferences from the Edit menu and navigate to the Advanced tab in the resulting window. You'll see them at the top of the General "sub-tab."

Coming soon: iTunes Switch 201 and 301

In a future installment of this series, I'll examine how you can take this iTunes migration to the next level and move to Windows Media Player or the Zune PC software. And after that, we'll visit crazy town: A full Apple-to-Zune conversion across the board. Yes, it's possible.