I've hit a roadblock at work this week with some Windows Server 2016 and 2019 machines. We can't remote into the servers at all. When I try RDP, it prompts for credentials, but after filling those in, I get a quirky warning about using a company device that ends with a bizarre joke. After pressing 'OK,' the window just closes.
Attempting to access via the hypervisor console also gets me to a 'Press CTRL+ALT+DEL' screen, but when I do that, the lock screen pops back up without any error or warning—super frustrating!
Interestingly, this issue only affects the servers running 2016 or 2019. Everything else on 2022 and 2025 is working fine, but upgrading is impossible since we can't log in to these VMs.
I've ruled out network issues, firewall changes, and policies, having isolated a server with no GPOs applied. I also ran DISM and sfc /scannow through WinPE, but no luck there either. We've opened a ticket with Microsoft after spending several days trying to troubleshoot these servers. They're not ransomwared—all files are accessible, and jobs seem to be running normally. So, if anyone has any ideas before the weekend hits, I'd love to hear them!
5 Answers
Have you tried connecting via the server's IP address instead of its name? Sometimes that can make a difference. If you can connect but the session closes immediately, it might give you clues to investigate further.
If you're using Hyper-V, have you tried disabling Enhanced Session Mode? Sometimes that could be causing issues. Just choose to connect using a basic session.
It sounds like there might be a policy affecting your RDP sessions, especially since you've seen that warning message. Have you checked the group policies thoroughly? If you could find the source of that custom message, it might lead you to the problem. What exactly does the warning say?
If possible, try to get remote CLI access to your server. You could export the event viewer logs via CMD to see if there are any hints about what's going wrong.
Another route you might consider is booting into safe mode. It could help you bypass whatever's causing the login issue.
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