Unable to Access w/Remote Desktop Until a Local Logon w/Password is Performed

hsehestedt · Aug 16, 2022

I had an issue recently where no matter what I tried; I could not access Windows 11 Pro systems via Remote Desktop. I would repeatedly get an error saying that my credentials were invalid, but I knew with 100% certainty that my credentials were valid.

I finally figured out a solution, but I'm completely confused why this worked. I was wondering if anyone had a clue why this is necessary. Here are the details:

On the systems in question, I log on with a Microsoft account. When I log on locally, I use a PIN to log on. It turns out that the solution is to simply log on to the local system one time by password rather than by PIN. Once I have logged on once, that's all that is needed. From then on, I can log on via Remote Desktop, even if I reboot the system.

Any thoughts?

cereberus · Aug 16, 2022

hsehestedt said:
I had an issue recently where no matter what I tried; I could not access Windows 11 Pro systems via Remote Desktop. I would repeatedly get an error saying that my credentials were invalid, but I knew with 100% certainty that my credentials were valid.

I finally figured out a solution, but I'm completely confused why this worked. I was wondering if anyone had a clue why this is necessary. Here are the details:

On the systems in question, I log on with a Microsoft account. When I log on locally, I use a PIN to log on. It turns out that the solution is to simply log on to the local system one time by password rather than by PIN. Once I have logged on once, that's all that is needed. From then on, I can log on via Remote Desktop, even if I reboot the system.

Any thoughts?

I manually set credentials usin credential manager.

hsehestedt · Aug 16, 2022

cereberus said:
I manually set credentials usin credential manager.

I think I'm not following. Credential manager will store the credentials so that I do not need to manually enter them, right? In my case it is not that I cannot recall the creds or enter them correctly, the issue is that even if you enter the correct creds, you will be denied UNTIL you go to the machine you are trying to connect to and logon with the password locally at least one time. This is a one time operation - once you logon once it will from then on work forever without having to ever logon on locally with the password again. I was just curious what's up with this weird behavior.

cereberus · Aug 16, 2022

hsehestedt said:
I think I'm not following. Credential manager will store the credentials so that I do not need to manually enter them, right? In my case it is not that I cannot recall the creds or enter them correctly, the issue is that even if you enter the correct creds, you will be denied UNTIL you go to the machine you are trying to connect to and logon with the password locally at least one time. This is a one time operation - once you logon once it will from then on work forever without having to ever logon on locally with the password again. I was just curious what's up with this weird behavior.

I just found entering them manually seems to bypass odd issues.

glasskuter · Aug 16, 2022

I think the explanation giver by user Stephanie on this page (about halfway down the page) is the answer. Windows 10 Remote Desktop Credentials

hsehestedt · Aug 16, 2022

glasskuter said:
I think the explanation giver by user Stephanie on this page (about halfway down the page) is the answer. Windows 10 Remote Desktop Credentials

Bingo! Good find. To summarize, if you initially log on to the system using a passwordless mechanism such as a security key (that's exactly what I did), it is then necessary to log on using the password so that the system can save the local password hash. It's only necessary to logon one time ever.

Funny that I stumbled on the solution first, but not the reason why logging on worked. Now I get it!

Ed Tittel · Aug 18, 2022

Thanks for all the great info on this topic. Blogged about it earlier this week: MSA RDP Login Issue Resolved - Ed Tittel. I learn more here at ElevenForum than in any other half-dozen places on the 'net!
--Ed--