A second Windows update.

Published: Apr 15, 2026

Have you ever woken up, and fearfully remembered you have a class that's just about to start? Only to remember that you're in your mid 20's or perhaps even older? We have all been there. However, as an IT professional I feel that instead of dreaming of a forgotten class, I will be dreaming about a Windows update.

Today, Microsoft has released a security update. Specifically, around their Remote Desktop security. I do not have a problem with security, I actually prefer things to be configured securely. However, I do have issues with Microsoft's implementation time and time again. These "warnings" which are scaring everyone and their brother, didn't just appear today or overnight. They have in fact been here the entire time. Most IT folks are probably familiar with the old verbiage, which is less dramatic and says essentially the same thing as now. I have come to conclude that this is Microsoft shifting the liability from themselves onto the IT team, which is fair enough. But is this the best way to do it, a big scary change in wording overnight without any warning or foresight? I am not sure.

Alas, I am now receiving calls from frantic users, other IT vendors, and so on... about something that very much has always been the case. But I figured this would be another great chance to complain about Microsoft, which I will do whenever I get the chance to do so. So thank you Microsoft, for giving me perpetual bad dreams! I must go now, the phone is ringing...

https://learn.microsoft.com/en-us/windows-server/remote/remote-desktop-services/remotepc/understanding-security-warnings