Q: I just bought a new iPod shuffle, but when I plugged it into my Mac I got a message that I needed iTunes 10. When I tried to install iTunes 10 I got a message that I needed Mac OS X 10.5. Is this something I have to purchase? Is it not a free update? I’m pretty miffed that I can’t use the new shuffle without having to pay more. Any help, advice or suggestions would be great. I’m not that computer/tech savvy. Thanks.

– Zoe

A: Unfortunately this is the way that all of Apple’s product updates work. When new iPods are released there is usually an iTunes update that is released alongside them and they normally require that version of iTunes. Likewise, newer versions of iTunes require newer versions of the underlying operating system as Apple doesn’t want to continue supporting older versions of OS X, and in the case of Microsoft Windows isn’t even in a position to support versions of Windows that are no longer being supported even by Microsoft.

This basically means that you have three options. The first and simplest option is to pay for the upgrade to Mac OS X Snow Leopard (10.6), which comes as a $169 box set that includes iLife ‘09 and iWork ‘09. This has the advantage of ensuring that you’re on the latest version of Mac OS X and since it seems likely that you’ll run into this as a requirement for other software in the future, it may make sense to simply take the plunge.

Alternatively, you can look to third-party iPod management applications that are partial alternatives to iTunes. These applications are very unlikely to provide support for more advanced features such as VoiceOver on the iPod shuffle, but should at least allow you to get your music onto your device. A Google search for “iTunes alternatives” should turn up a number of options, but you may find that many of these have not been updated in recent years and therefore may not even support the new iPod shuffle at all. You will also find that options for Mac users in this category are much more limited.

Your third option is to simply return or sell your fourth-generation iPod shuffle and purchase an older model that still works with older versions of iTunes. The second-generation iPod shuffle may be a reasonable choice for basic music playback, although you’ll lose the VoiceOver feature and the ability to use more than one playlist—the third-generation iPod shuffle provides most of the same software features but lacks the physical controls on the device. In most cases you should be able to find older stock at some stores or even refurbished units directly from Apple.