If it’s not one thing, it’s another. Last week, Microsoft rolled out a patch that wasn’t received well by some systems. The impact of this started showing up on Memorial Day weekend as systems rebooted. Putting our clients first has always been, and will always be, our number one priority – regardless what day it is. When we first discovered that the Microsoft patch was causing some issues, our team went to work. The issue was researched, identified, an action plan was created, and communications to our clients went out.

We’re big advocates of Microsoft and the productivity tools they bring to the table – especially for mid-market businesses. While we love the tools, we have to admit that Microsoft has caused some disruptions with how they roll out security patches. We have a few thoughts on this, how it impacts businesses, and why it is important to have an advanced tech team in your corner.


We fully understand the importance of security patches. If we said any different, our Enhanced Security Services team would be in our CEO’s office giving him a long heart-to-heart. However, because of how quickly technology and operating systems advance, when universal security patches are rolled out, it can have unintended negative impacts. Security patches are necessary – yes. But they aren’t always completable with the technology.

We saw this one year ago with the memorable “Microsoft Zero Day Patch”. We reflected on the chaos it caused and you can read about it here. One year later, over Memorial Day weekend, we experienced yet another Microsoft patch that cause functionality issues with the NIC card, which is what allows the system to connect to the internet. The patch issue was narrowed down to only affecting Windows 7 workstations and Windows Server 2008 servers.

The issue we see with universal patches being rolled out is this: not every company is up to date with the Windows operating systems. Microsoft is desperately trying to push every company forward with having the latest versions, but that simply takes time and can be an heavy investment for some.


In the case of the patch incident over Memorial Day 2019 (which we’ve coined ‘Patchapalooza’), not everyone was impacted negatively by the roll out. Only companies who had Windows 7 workstations and Windows Server 2008 had issues. It should be noted that Windows 7 and Windows Server 2008 have a slated End of Life date of January 14, 2020. There has been a mad rush to upgrade considering Microsoft will stop releasing updates and patches – and since the patches they are currently rolling out keep breaking things on Windows 7 and Server 2008!

We understand that there is the issue of legacy applications and software that can only run on outdated Microsoft versions. Believe it or not, there are some systems that can only run on Windows XP. This is a conversation for another time, but this poses a big issue for many companies, especially those in manufacturing. If your business runs on an application that only operates on a version of Microsoft that is no longer supported, or has a looming end of life date – what do you do? Unfortunately, there isn’t a simple answer, which leads us to our next point.


Planning for technology in your business is crucial. Our businesses operate and depend on our applications, data and the functionality of our network. It has to be a priority to plan and have a roadmap for technology upgrades. The biggest problem is often that too much falls on an internal tech team. Whether you have a team of ten or a lone ranger managing your internal technology operations, it is a vast responsibility considering the technology industry changes faster than most can keep up with.

Chances are, you checked out of the office on Friday looking forward to a nice long holiday weekend. If your IT team wasn’t monitoring the effects of the recent Microsoft patch, you wouldn’t know any different until Tuesday morning. And who likes to walk into work after a holiday weekend with workstations not working, frustrated co-workers, and the word every CEO hates: “unproductivity”.

It’s a lot to manage and we get it. This is the sole reason why we do what we do. We are in the problem-solving business for a reason – so you don’t have to worry about it. We take care of the little things – and the big things like Microsoft patches gone wrong. We also help you take care of the big things like planning for upgrades, security and how technology is used to keep your business moving forward. This is why you need an advanced tech team in your corner to always be monitoring your systems, even on a holiday.