Pandemic Week 10 – To Update or Not Update

If there is one conversation I have almost on a daily basis with clients, family and friends, it’s about whether or not they should update their various devices, and especially their Windows computers. In times past (maybe 5 years ago) this was easy to answer, “Yes, always keep your software up to date.” Today, particularly in light of Microsoft’s latest Windows 10 update causing widespread havoc for many users (again!), the unfortunate punchline is now, “Maybe? It depends.”

Nobody likes that answer

It’s safe to say that when clients come to us with technical questions they would prefer situations to be a little more black and white. For certain things we can always say, “Yes, please apply the updates.”

1. Your malware protection should always be kept up to date.
2. Your smartphones should always have the latest operating system.
3. Your firewall firmware should always be updated.
4. …

I’m sure there are a few more, but unfortunately, the list of definitive “Yes’s” has become a lot shorter lately. Sadly, Microsoft is has moved to the top of the “Maybes” list, due in large part to their inexplicable decision in 2015 to source their testing and bug-checking to the public (via the Windows Insider program) instead of in-house QA which had worked fairly well for them up through Windows 7. Outsourcing testing of your products to millions of “real” users seemed like a great idea at the time, but unfortunately, it has resulted in much lower quality (and at times, disastrous) updates. The infinite monkey theorem has a corollary here in that while millions of “real” users can test an update, a well-trained team of QA testers could do it faster and produce better quality results without destroying user data.

“Should you be updating your Windows operating system?”

Frankly, Microsoft doesn’t really give you many options for deferring updates without taking rather draconian measures to circumvent their forced march. On top of this, other software platforms that professionals use to get their work done are also trying to match Microsoft’s inexorable update pace with their own updates, and everyone is trying to stay ahead of the criminals. As a result, we seem to be assaulted with a constant barrage of changes that at best don’t break anything, and at worst, break everything. All that being said, our answer is still “yes” but with the caveat that one should plan to apply updates, not just blindly apply them as they appear. When making a decision to update (if you are given a choice) you should always ask yourself these questions:

1. Is my data backed up?
2. Do I have some other way to do my work if this breaks something?
3. Is this update fixing a serious security issue?
4. Is this update fixing a serious operational bug?
5. Is now the right time to be applying an update?

The last question is probably the trickiest one to answer. Oftentimes, an update can lead to some downtime, either while it’s being applied, or perhaps while it’s being rolled back because the cure was worse than the disease. If you’ve got important work that needs to be done now, perhaps defer that update a few more hours, but don’t forget to come back to apply it.

Image by thedarknut from Pixabay