Had a laptop that receives Windows 7 security updates (licensed on 2 year ESU) and would not remote into the office. The error message referred to the SSL certificate connected to the RDgateway being out of date, but the certificate was valid.
I ended up having to install KB2574819 An update is available that adds support for DTLS in Windows 7 SP1 and Windows Server 2008 R2 SP1 (microsoft.com)
Note that this update is also offered up as an optional update in Windows update but since I don’t typically install optional updates, I didn’t install it on that laptop.
Just a fyi in case you hit this head scratcher and think your Win7 might need a root certificate bundle.
Susan Bradley Patch Lady/Prudent patcher
