October Win 10 Update: Dealing with the Repercussions, Preparing for the Future

An “Update Available” notification is something we usually are happy to receive. Maybe your device will run a little faster, some pesky bugs will be squashed, battery life will last a bit longer, or a few cool new features have been added. However, system updates can unfortunately also be accompanied with unintended consequences–some much worse than having to click through on a new set of terms and conditions fine print or resetting your password.

An update to key applications or an operating system can sometimes transform a perfectly functional computing environment into a nightmare of lost productivity and missing data. Not only might the update itself miss some critical flaws during its own quality assurance testing, but once unleashed in the real world it can also have some pretty devastating impacts on end users who were simply clicking “OK” on a friendly pop-up screen or had their system automatically updated by a technician.

Balancing Patience with Prudence

For MSPs, the motivation for upgrading software is obvious: Patching security flaws and preventing threats from penetrating client systems is why many clients hired you in the first place, and we all know that system updates are essential for ongoing protection from the bad guys. However, unfortunate potential outcomes when a vendor releases a new version of a product can include failed updates, updates that cripple key functionality, or updates that grind performance to a halt or even permanently lose or corrupt data.

While this is problematic when you opt to install an update yourself, it is even worse for your customers. They trusted their service provider and experienced devastating consequences. This is why MSPs must resist the urge to blindly upgrade the moment an update becomes available and instead take the time to ensure each upgrade is not only timely but also successful.

The Win 10 Challenge

Windows 10 has proven to be particularly troublesome when it comes to upgrades. For starters, Microsoft began charging a monthly fee for users to get important system updates. In addition, some users have experienced actual data loss with the operating system’s 1809 update in October, including the permanent loss of documents, photos, and other personal and business data.

Many in the industry–including Microsoft itself–are now advising against this upgrade, which creates a dangerous precedent in a world where vendors are constantly striving to stay one step ahead of malware and other security threats. With almost half of all Windows users already running Windows 10, and more than one-third of all computers using this Microsoft OS, it’s also a potentially massive disaster waiting to happen.

Simple Steps to Avoid Big Problems

For an MSP tasked with protecting its customers’ data, it is essential to be up to speed on these types of developments so you can be appropriately vigilant instead of rushing updates into production before they’re proven to “do no harm.” One way to remain informed about what’s happening with different vendor updates is to rely on a trusted and comprehensive knowledgebase.

This creates not only a centralized and fully accessible inventory of every endpoint on the network and its current upgrade status, but also a common platform for noting which systems shouldn’t be automatically upgraded when there’s a troublesome update available.

For many service providers, this means there are several options to consider. Can you upgrade some internal or customer computers a little earlier than others to ensure there are no issues with the upgrade? This proof-point is especially critical for line-of-business applications. Another factor to consider is to how quickly you need to upgrade. While you don’t want to leave anyone at risk, in some cases it’s more prudent to wait a week. 

There is also the human element to consider, including figuring out when is the most convenient time to schedule an update and communicating to end users so they’re not surprised when it suddenly takes 10 minutes to reboot their laptop after a forced restart when they’re worried about deadlines. 

And, of course, ensuring users’ files are backed up in some fashion before every upgrade is a no-brainer–even though plenty of people don’t bother, and in some rare cases suffer some severe consequences if the update goes awry. 

All MSPs are invited to view Kaseya’s free, on-demand webinar “Installing Windows 10’s October Update,” which covers these topics and more. Not only will it help you prepare for “Redstone 5,” but it also provides a set of best practices applicable to any Windows 10 update.

This guest blog is part of a Channel Futures sponsorship.