Pleasant Password Server is an award-winning multi-user password management tool compatible with “KeePass Password Safe” and Bruce Schneier’s “Password Safe”, the most popular password management systems in the world. Here are some Errors associated with Pleasant Password RDP SSO and SSH SSO.

Error One: Wrong username or password when authenticating with the target server

Solution: I was connected to the password server with a different credential (Administrator) and I wanted to open or initiate an SSO RDP connection with my Username. This did not work as it tried using the default administrator credential

- What I did was to logout the Administrators account
- Logged in with my regular account 
- Tried initiating an RDP connection and this worked

Second error: Claims regeneration because mismatch detected

There are a whole lot of answers to this problem but trust me in this case, they are not applicable.

Explanation: This error means, that on the server you are trying to connect to has NLA activated.
– Unfortunately the RDP protocol version used in PPS is not supporting NLA. So you would need to switch of NLA on the destination server in order to be able to connect.

Solution: I resolved this issue by using the default port of 7070 and not the RDP default port of 3389.
Note: You make to create firewall rules in the VM and also on the firewall to allow this connection.

I hope you found this blog post on Errors associated with Pleasant Password helpful. If you have any questions, please let me know in the comment session.