Starting sometime in April, every Windows 7 user eventually started getting nagged by Microsoft while they work. Much like kids tugging on your pant leg while you’re trying to talk to a sales clerk, I’m sure it will be very low key and appreciated worldwide.


Upgrade To Windows 10

Chances are, if you’re a Windows 7 user, you didn’t want to upgrade before, and you might not want to now. But of course, much like a trouser-yanking child, Microsoft doesn’t entirely care what you want.

Until sometime in 2016, upgrading from Windows 7 to 10 was free. If you declined, I promise I’m not judging. Back in the day, I was an XP purist. Not until the bitter end, but I remember the pitfalls of Windows 98, Millennium Edition*, and 2000. When XP was released, it was stable, aesthetically nice, and functional. In the IT community, there was great rejoicing because this was the first useful Windows version that didn’t look like an early-90’s web page. Windows 7 is in roughly the same situation. I didn’t want to upgrade either, but it’s time to let Windows 7 go.

I grant you the track record is not in Microsoft’s favor. After the XP release, the next OS (Vista) was beset by bugs and countless foibles. Much of the goodwill that Microsoft had built up with XP was “Vista-ed” by the time Windows 7 had released. People hung onto XP as though it was the last useful version, which was the case for some programs. Crossroads IT definitely has clients that can only run specific programs on legacy systems, and it can be a tough situation to navigate.

By 2010, XP was aggressively being abandoned by Microsoft from nearly every standpoint. A high percentage of the world was still using XP and the end-of-life date was being screamed from the rooftops as a warning to the millions of users. April 8, 2014, support was terminated and those machines with the OS still installed were left in the cold.


What Is Microsoft Support?

You might be asking: “XP didn’t stop working… What exactly does Windows support provide, and why does it matter?”

Generally, few people are going to be calling Microsoft directly for Windows OS support. I have, and trust me, you don’t want to. If you’re lucky enough to even find a number, it’s a red nightmare of prompts, loops, and dead-ends. Microsoft’s support is considered more on developmental side. During the period software is supported, they continue to address flaws, create security updates, patches, and improvements. When an OS goes end-of -life, it’s no longer addressed in any way.

Microsoft’s abandonment made the end of the XP support particularly dangerous for those who didn’t (or couldn’t) upgrade to the next version. The OS was widely used and bad-actors knew it. They could develop ways to exploit flaws in XP, and they had a hard date on which Microsoft wouldn’t bother addressing them. If people didn’t upgrade, they were potentially sitting on incurable time-bombs.


Enter 2019

Despite Windows 7 still being run on 40% of the world’s computers, the support of 7 ends in January, 2020… hence the nagging. Microsoft wants to give everyone enough time to make preparations for the switch to Windows 10.

Windows 10 is fast, surprisingly intuitive, and easily Crossroads IT’s favorite version to date. There’s a touch of a learning curve, but being comfortable riding horses doesn’t make a Ferrari any less impressive. Give Windows 10 some time, and you’ll be more proficient at it than you were with previous versions. Additionally, from a support standpoint Windows 10 is really simple to work with. It benefits everyone.


Extended Support If You Need It

If you’re especially attached to Windows 7, you can keep using it, but you’re on the clock. Everything turns back into a pumpkin in January. Microsoft learned a few lessons from their XP days, and they derived a way to make some coin off people’s hesitation to switch:

“Today we are announcing that we will offer paid Windows 7 Extended Security Updates (ESU) through January 2023. The Windows 7 ESU will be sold on a per-device basis and the price will increase each year,” – Jared Spataro, Corporate Vice President for Office and Windows Marketing

The offer of extended support begs the question: What to do? The clear answer is to upgrade anyway. Costs associated with ESU haven’t been released yet, but given how Microsoft structures their pricing models for other offerings, there’s little doubt that you’ll pay more for a 6-month ESU subscription then the cost of a Windows 10 license. And truthfully, ESU updates are simply staying the execution, Windows 10 is coming. Taking the time to make the change and ensure your office is compatible with the new version is important. **


There Can Be Only 10

Microsoft has stated that Windows 10 will be the final core version of Windows. They’ve employed a Software as a Service (SaaS) model which ensures that the software is continuously developed against and updated accordingly. Normally, the SaaS model sees 3-4 major updates deployed throughout the year, and multiple minor update and tweaks. Certainly, this doesn’t suggest Windows is flawless, but you can take steps to mitigate “Zero-Day” problems. Windows 10 can be configured to delay the application of major updates after a specified amount of time (up to 6 months). This allows you to avoid struggling with potential incompatibilities, and gives Microsoft time to deploy fixes for bugs that they failed to catch during development.


Let’s Do It!

If you’re convinced that Windows 10 is the best way forward, and that paying handsomely for the delay is not worth it, then I would suggest Crossroads IT to assist.

Crossroads IT can make this upgrade relatively seamless.

  • We’ll take care of procuring the licenses, and administering the upgrades.
  • We’re happy to come in after-hours to make sure you and your staff lose minimal productivity.
  • We can host a small Q&A session for any burning questions. Understanding is key.
  • Most importantly, if you have older software, we can do the research and perform the tests to catch any potential problems before deployment. The surprise of having software stop working on day 1 is overrated.

Times, they are a changing. With proper planning and some professional insight, you can easily change with it.



* – ME serves both as a grave warning to early upgraders, and Microsoft’s dirty little secret that everyone tries to deny ever happened.

** – Crossroads IT is able to perform testing any important software you have with the newest version of Windows 10. As Windows 10 releases major updates, we’re updating our machines as well, so we’re in the thick of it. Conversely, we also have experience rolling back updates that may have caused problems. Troubleshooting Windows wouldn’t always be considered graceful, but you aren’t alone in this.