Remote Desktop Prompts for credentials twice

Question

We have two new windows 2012 R2 servers that have been passed over to us we have a bit of an issue when trying to connect to these machines which I am unable to resolve.

The issue that we have encountered is that the new windows 2012 machines are prompting for credentials even AFTER the REP client has passed them through, this happens both when the credentials are entered manually and when they are stored in the client and passed through automatically.

Step 1 & 2: RDP Connection Dialog & credentials

Step 3: Enter them again once the session connects

This does not happen on any of our other machines, just the two newest ones.

Normally this wouldn't be a problem but we have an automated process which requires the RDP sessions to be connected to work - there are 25 RDP sessions needed on each server for this and entering the credentials 25 times is going to be a pain for whoever needs to maintain this going forwards.

Help/Advice appreciated.

Answer 1

There are 3 group policy settings to check:

• One on host: “Always prompt for password upon connection”
• Two on client: “Prompt for credentials on the client computer” and “Do not allow passwords to be saved”

Remember to do gpupdate /force and check the actual values with rsop.msc.

If nothing works, consider using alternative RDP client, whith better logon automation:

• mRemoteNG
• RDCMan

Also take a look at the following Windows Feedback Hub item: normal or for windows insiders and consider up-voting it. There's a tiny chance that this would help as well.

PS. Here's yet another similar issue.

Answer 2

Everything I tried from my researches didn't work!

I found the solution myself when I deleted the RDP connection (credentials and everything else) on my client machine and re-done it and voila! It worked like a charm!

It hopefully this will help somebody else.