Sysadmins Wrestling with Microsoft Updates
10 posts since Jul 2026, all from r/sysadmin.
“Hi all, My organization uses snapshots (Previous Versions) on our file system. In Windows Explorer, users can open the Previous Versions tab and restore files themselves. We recently ran into an issue where a user attempted a restore but didn’t select all the necessary files…”
“We are noticing on several UPS WorldShip stations "Internal Application Error" after applying the latest update. These are all stations running V29 (2026) and just applied the latest update. Anyone else having this issue?”
“Has anyone run into this issue with Microsoft Remote Help? Remote Help has been working fine in our tenant for about two years. Recently, when I click Get a security code, I receive: "It looks like you don't have the right permissions to help the other person." Nothing changed…”
Several posts highlight challenges and frustrations related to Microsoft updates, including Secure Boot certificate rollouts, Windows driver enforcement, Teams Phone pricing changes, and issues with Remote Help. Sysadmins are struggling with implementation, unexpected costs, and communication around these updates.
SOURCES (10)
“WDS with MDT... yeah it's deprecated but it still works. When that dies I'm going back to flashdrives and unattend.xml files. WDS is the only PXE boot solution that passes Secureboot, FOG doesn't (please stop suggesting it, please). Autopilot/Intune aren't imaging, they are configuration tools.…”
“I tried to install Win 11 Pro via WDS only however I encountered many difficulties like unable to skip format disk window then I tried WDS together with MDT and now I can setup the win 11 pro basically fine. MDT runs nearly unattend besides of setting a computername which is fine since I want to choose the computer name. Then I deploy the NinjaOne agent per Immediate Task via GPO which nearly immediatly deploys the Agent as soon as MDT does the domain join. Topic is that i tried that all only in”
“Microsoft installs the BucketConfidenceData cab file, which contains the Secure Boot High Confidence Database for all devices, onto Windows consumer and enterprise devices (Windows 11 version 24H2 or later) through cumulative updates. The file is installed on devices where Microsoft is rolling out features and updates grouped by behavioral attributes (BucketID).The system places the file at %SystemRoot%\System32\SecureBootUpdates\ so that Windows can evaluate Secure Boot certificate update readi”
“We previously had 50 Teams Phone (US 1) licenses. 25 for $9, 25 for $8. Totalling 200 and 225 (I dont know why the same thing is split up?). Paid monthly on year contract. Last Month apparetly it got switched over to MCA, cancelled 25 licenses, and doubled the price. They are now all 17.85. So we have half the licenses at literally more than double the cost. I know prices were going up but it was a dollar or two. Not only that but apparently MOSA is billed at end of cycle, and MCA is billed at b”
“Hi all, My organization uses snapshots (Previous Versions) on our file system. In Windows Explorer, users can open the Previous Versions tab and restore files themselves. We recently ran into an issue where a user attempted a restore but didn’t select all the necessary files, which ended up causing more problems than they solved. Is there a way to restrict access so that only designated admins can use the Previous Versions feature? Ideally, regular users wouldn’t be able to restore or overwrite”
“We are noticing on several UPS WorldShip stations "Internal Application Error" after applying the latest update. These are all stations running V29 (2026) and just applied the latest update. Anyone else having this issue? submitted by /u/jdizzlez [link] [comments]”
“My company produces a Windows device driver and we were caught off guard by the Microsoft April 2026 driver enforcement. We signed up for the Windows Hardware Compatibility Program to get our device driver signed. They do real-world verification on your company and the individual signing up for the program. Yet after seven days I still do not have any workspace showing in my portal. I'm expecting to see a hardware workspace there, but they only option under Workspaces is 'My Access'”
“Has anyone run into this issue with Microsoft Remote Help? Remote Help has been working fine in our tenant for about two years. Recently, when I click Get a security code, I receive: "It looks like you don't have the right permissions to help the other person." Nothing changed on my side except I decreased the licensing count for the Microsoft Remote Help, and it set to 'Schedule this change for', although I'm not certain that's related but I have a strong suspicion”
“https://techcommunity.microsoft.com/event/windowsevents/oem-secure-boot-office-hours/4530352 Have questions about how device manufacturers support the Secure Boot certificate update process? Join OEM Secure Boot Office Hours to connect directly with OEMs and get answers to your questions. You can follow upcoming events here: https://support.microsoft.com/en-us/topic/updates-and-announcements-313b5279-2a3b-438a-83a5-3d5e2c5fc4a3 submitted by /u/Smart-Definition-651 [link] [comme”
“https://techcommunity.microsoft.com/event/windowsevents/secure-boot-office-hours-for-virtualized-environments/4530355 For one hour, experts will be available to discuss Hyper-V, Azure offerings, Windows 365, VMware, and other virtualization scenarios. Whether you're still planning for certificate updates, validating your rollout, or troubleshooting an issue, come get the answers you need from the people closest to the technology. You can follow upcoming events here: https://support.microsoft”