Moving iTunes Files To a New Computer

There’s no other major item most of us own that is as confusing, unpredictable and unreliable as our personal computers. Everybody has questions about them, and we aim to help.

Here are a few questions about computers I’ve received recently from people like you, and my answers. I have edited and restated the questions a bit, for readability. This week my mailbox contained questions about moving iTunes files to a new computer, file-compressing programs and security software.

If you have a question, send it to me at mossberg@wsj.com, and I may select it to be answered here in Mossberg’s Mailbox.

I recently bought an Apple iBook to replace an old Dell laptop. How do I move my iTunes music files from the Dell to the Apple?

Your iTunes music files work on both Windows and Mac machines, as does the special iTunes Library file that keeps track of play lists and the like. So, all you have to do is copy these files from the Dell to the Apple, as with any other files you want to move. In fact, even if you were moving from an old Dell to a new Dell, without changing operating systems, the process would be the same.

If you have allowed iTunes to gather all of your files into the folder called “iTunes” within “My Music,” all you have to do is copy that folder to the iBook. This can be done in a number of ways, but the best choices would be to do this via a home network or by burning the files to CDs or DVDs and then copying them from the CDs or DVDs onto the Mac. On the Mac, the iTunes folder is usually located within the Music folder.

If your music files are scattered, or are in the My Music folder, but not the iTunes folder, you’ll have to locate them before copying them. Be sure to copy the iTunes folder also, because it contains the iTunes Library file.

If you have an iPod and it contains all of your songs and play lists, you can skip these steps. Just download one of the many cheap utility programs for the Mac that will copy the contents of an iPod to a computer. Two examples are PodWorks and PodUtil, the latter of which comes in a Windows version for Windows-to-Windows transfers.

One more thing: Be sure to deauthorize the Dell from your iTunes account before authorizing the Mac, so you don’t waste one of your maximum of five slots for computers that can play any songs you purchase. To do this, fire up iTunes on the Dell, go to the Advanced menu and select “Deauthorize Computer.”

What program do you recommend the most for compression and decompression of files? Winrar, WinZip or any other program?

On Windows, I use WinZip (www.winzip.com), because of its flexibility, even though the operating system can compress and decompress files by itself. On the Mac, I use Stuffit (www.stuffit.com), for similar reasons. A decompress-only version of Stuffit came with earlier versions of Mac OS X, Apple’s operating system. The current version of OS X, Tiger, can compress and decompress files in the popular Zip compression format without Stuffit.

I run Norton Internet Security, Ad-Aware and Spybot on my computer to keep “bad stuff” from infecting my system. Yet last week a malicious program attacked my computer. It hijacked my wallpaper and put a huge warning on my desktop. My security software never knew it was there. Do I need to run additional security on my computer?

This category of spyware or adware is expanding so fast that, even with the two good anti-spyware programs you are using, attacks can happen. My only advice is to add a third, such as Webroot’s Spy Sweeper, which is my favorite. I know this is annoying, but until the spyware/adware epidemic slows down, it is often necessary for Windows users to have multiple defenses.