If you have ever read an article on computer security, the odds are pretty good that you have seen the advice to make sure all your software is up to date. And if you have interacted with people’s machines in the real world, you also know that very few people fully heed this advice. Software vendors are always looking for new ways to entice or enforce updates, to ensure people have the best possible software experience, including safety. Is Apple’s recent move to offer OS X 10.9 Mavericks as a free update one of these maneuvers?

When it comes to updating the OS, almost every vendor has a hard time getting people to make the move. Microsoft has been feeling this pain exquisitely, over the last six years. Despite being over 12 years old, getting people to migrate from Windows XP has been like pulling teeth. Microsoft has already moved back the End of Life support date, though it looks like next April will well and truly be the end of this popular OS version. Maybe. That is, if they can get the Windows market share of XP below 10%. As of September of this year, it was still at over 30% of the total desktop OS market share though it had dropped 2.25% in the previous month. Windows 7 has over 46% of the market share, which is a healthy percentage, comparatively speaking.

But Microsoft is by no means alone in this OS update struggle. Google’s Android has a similar problem too, although hardware compatibility creates a potentially bigger hurdle for updating Android than with other operating systems, due to the large number of hardware manufacturers and many different and not necessarily compatible handsets. As of the beginning of October, Jelly Bean powers 48.6% of Android devices, though the largest percentage (36.5%) is still using some level of version 4.1 rather than the latest, which is 4.3. Another 28.5% are still using Gingerbread, which comprises the 2.3 versions.

Naturally, Apple OS X has its problems in this area too, as the bulk of their market share is pretty evenly distributed between the three latest versions, 10.6 through 10.8. At the time of writing, more than 37% of Mac OS users are on the last version of the OS, OS X 10.8, dubbed Mountain Lion. Almost another 42% are on the previous two versions of the OS, Lion (10.7) and Snow Leopard (10.6), the latter of which was released almost five years ago, around the same time as Windows 7.

But wait… that’s not all!

There is one OS ecosystem that does not have a problem getting rapid and widespread updating, and that’s Apple iOS. At the time of writing, iOS 7 had over 76% of the iOS market share, and the previous release, iOS 6, had just under 21%. That’s a very different picture from the rest of the OS market. What is Apple doing differently than every other OS vendor?

With both Windows and Android, there’s a significant amount of choice available for hardware. While this abundance of choice does have its benefits, it can make updating the OS in a timely fashion difficult if not impossible. Apple keeps tight control over hardware, and though some users have found a way to install Apple operating systems on unsupported, non-Apple machines, this is decidedly a niche market. For the most part, Apple users are deeply entrenched in a walled garden that ensures compatibility between the OS and current hardware. Users that aren’t able or willing to upgrade their hardware may not be able to update, and this may explain why there’s still such a large percentage of Snow Leopard users.

However, just because people can update doesn’t mean they will. Clearly, there are other factors. Popularity could figure into that, but it’s a very difficult thing to measure. And plenty of people update only to find that they dislike the new version, but are not able or willing to figure out how to downgrade. Which leaves the last remaining factor: Cost.

It’s not exactly an Apples to Apples comparison (no pun intended) to compare the cost of previous OS versions historically. Because of Apple’s control over hardware, it can be more expensive than similar hardware used to run other operating systems. Therefore, it could be considered part of the cost of the OS. In effect, the hardware is the software license. But there is one big difference in cost because of the recent move to make Mavericks updates free for all users of Snow Leopard and above, which is that it encourages people using 5-year-old versions of the OS to update. This would be roughly equivalent to letting Windows 7 users update to Windows 8.1 for free.

The tactic appears to be working, too. At the time of writing, a week and a half after the official release of Mavericks, it accounts for more than 18% of Mac OS traffic. Windows 8 adoption after almost exactly a year has reached only 8% of total desktop market share. Again, this is not a direct comparison as that 8% comes from a figure that includes other operating systems. When a total OS ecosystem has just shy of 8% of the total desktop market share as OS X does, increasing your percentage within that slice of the pie takes far fewer individuals.

That said, from a security perspective, updating is good. And something that creates a dramatic level of updating is awesome. This policy of free updates for older operating systems may not be something that is feasible for Microsoft to adopt, but it’s likely that getting users to leave older operating systems will continue to be painful for the foreseeable future, without that change.

What do you think about free operating system upgrades? Should they be standard for updated users? Or should the be available to older OS' users as well? Leave a comment and let us know.