I feel like crying every time I see someone running an outdated version of WordPress. Often, they cite issues that cropped up in the past as reasons for not upgrading and defend their outdated software passionately.
Coming from a Windows background, I understand the hesitation that comes with clicking "update now." With various applications produced by differing developers running on your machine, the likelihood that a driver update or library upgrade will destroy an already-working system is quite high. Actually, this is one of the major drivers behind certain businesses still using Windows XP.
They've reached a level of stability in their infrastructure they aren't willing to risk with a software upgrade.
The Parent Test
Once upon a time, I worked for a tech startup that used the "mom test" to determine the usability of our software and its subsequent upgrades. After wordsmithing guides and troubleshooting the application, we shipped things off to the founder's mother. If she couldn't figure it out, the process was too difficult. If she made a system-bricking mistake, then it was back to the drawing board.
A bit radical, but it made a point.
I usually see the largest collection of non-upgraded software when I help my parents set something up on their machine. Windows Update is disabled by default because it's, in the past, completely bricked their machines. Instead, I help them upgrade things from time to time so I can be on-hand if anything goes wrong.
As a result, I recommended they switch to Mac when they got their next machine. The "walled garden" approach of the Apple ecosystem was attractive; Apple-branded software running on Apple-branded hardware. What could go wrong?
Failure of Walled Gardens
I've had a Mac for a little over a year now, and had very few issues with it. Unfortunately, the issues I have had were crippling.
First, the video started acting up. In the middle of conference calls, my video would turn from a picture to several horizontal green lines. It took 3 trips to the Apple Store to get assistance with the issue; I only got support after proving the issue was present in Facetime (Apple product) and not just Skype and Google Hangouts. The tech who looked at my machine hit some sort of key command to put my Mac in a special diagnostic mode, and determined the camera itself had failed.
I asked what commands he used, and he refused to tell me. He said it was Apple's policy not to expose that information so end users wouldn't accidentally break their machines.
Thursday afternoon, I opted to upgrade to OS X Yosemite as soon as it was available. The upgrade went smoothly, and I figured I was on my way to a wonderful, flat-design experience.
Until I tried to watch a video on iTunes.
Somehow, during the upgrade to Yosemite, my Retina display forgot it was HD-capable and locked me out of all of my videos.[ref]Every attempt to play a video, through iTunes or QuickTime, results in an error claiming I'm using a device incapable of HDCP authorization ...[/ref] iTunes claimed my machine was incapable of HD playback and refused to play anything (ironically, not even SD videos). These were videos I purchased through Apple in an Apple-branded application on Apple-branded hardware.
And because of the closed ecosystem, my only avenue for help is Apple support.
When we see (comparably more-) open platforms like Android, Linux, and Windows suffer from upgrade hesitancy, it's incredibly enticing to move to a walled garden like Apple. The supposed promise that Apple's software will "just work" on Apple's hardware is soothing to those frustrated with hours of updates and, often, updates that just break a machine.
But when we see upgrade issues even in the closed system that break devices (iOS breaking the phone feature on the iPhone 6, Yosemite locking me out of video playback, etc), it's even more damaging to consumer's frail desire to stay updated.
So the next time you see someone running an old version of IE, or an older version of PHP, or an outdated version of WordPress ask yourself, what can we do to help consumers be less afraid of updating their system?