When should you upgrade your operating system?

You may always desire the latest and greatest, but does spending the money and time always make sense? The answer, as it turns out, depends.

For casual computer users, keeping in step the fast-moving computing world can be a frustrating conundrum. When does added convenience outweigh the price of an upgrade, and the burden of readjusting to a new environment?

If you’ve been humming along just fine with an old OS despite the arrival of Mountain Lion for Macs this summer or Windows 8 for PCs this fall, you may feel like an upgrade is pointless. But at some point, the age of your computer’s operating system is going to start blocking you off from the rest of the world. Your files and programs won’t be compatible with what they’re using at the office anymore. You’ll find yourself envious of the speed, new features and slick look of friends’ updated computers. What factors should you consider when deciding when to move on?

Cost, security, and the march of time

Security makes the most compelling reason to upgrade your operating system right now. If you’re still stubbornly clomping along on an OS that’s three versions or more behind the time, you’re missing out on years of important security updates for your system.

Cost can present a barrier, but the most recent OS upgrades from Microsoft and Apple have kept it to a minimum. Mountain Lion’s $19.99 price tag makes the upgrade a reasonable move for most Mac owners at any point. Updating a PC is usually more costly, but if your PC can comfortably run Windows 8, upgrading early can save you money. You can snag a Windows 8 upgrade for a mere $40 through the end of January 2013, and as low as $15, if recently bought a new Windows 7 laptop.

Another must-update situation exists if your OS version is so old that the manufacturer no longer sells or supports it. Somewhere around the five-year mark, you’ll fall off the back of the update cycle, and your system will be too old to handle further upgrades.

With this summer’s upgrade to Mountain Lion, Apple has committed to an annual upgrade cycle that mirrors what it is already doing with the iPad and iPhone. Older machines (think mid-2006 or earlier) that can’t keep up with the most recent versions no longer receive updates. Despite the Apple Software Update messages assuring you that your software is up to date, you’ve entered the dead zone.

With updates hitting about every three years, Windows fall behind the curve in just a couple of versions. PC users still relying on Windows 95, Windows Millennium, or Windows 2000 have definitely slipped into left-behind territory, and Windows XP is also getting precariously old and cranky .

Questions to ask

• Beyond those essential points, ask yourself what you expect to get from an OS upgrade.
• Is a hardware update what you really need?
• Would a good tuneup give you the performance boost you’re looking for?
• Is your computer powerful enough to run a newer version of your operating system?
• Is the rest of the software you use compatible? Will updating your operating system set off a cascade of other software updates?
• If you ever work from home, is the new version compatible with systems at work?
• Do you actually need or want the features a new OS version offers?

Ultimately, your operating system needs to be able to keep up with ongoing security updates and compatibility with current software. An OS released within the past five years should be up to the task. But if your computer can handle it and the price is right, the hop to the most recent release may be the smartest bet.