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Certain clients unable to connect to RD Gateway

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Afternoon all!

I have an interesting situation.  I work for a large company as a desktop engineer/SCCM admin.  We have a small group of users that take care of our clients' IT needs.  As such they require RDP access to their environments over non-standard ports and through RD gateways.  I have one situation where, no matter what I try, I can't RDP into one client via their RD gateway.  

Corp firewall and websense are not factors as I'm still unable to connect from the office, home or on a Verizon MiFi.  It's a domain-joined PC and the windows firewall is turned on by default, but I added it to an exceptions policy which allows me to turn the local firewall off.  Connecting from a personal PC, it works fine.  

I ran a wireshark sniff on the domain PC.  You can see it attempt to connect, but it never gets a reply from the gateway.  I can browse to https://remote.{clientsdomain}.com perfectly fine.  Checked event logs and nothing jumped out at me.

I also tried disjoining the PC from the domain, so I know it's not a GPO or anything like that...

Is there something obvious I'm overlooking?  Something like an SSL setting somewhere or other policy that may be set.

The error I'm getting is simply "This computer can't connect to the remote computer.  The two computers couldn't connect in the amount of time allotted.  Try connecting again.  If the problem continues, contact your network administrator or technical support," no code or anything along with it.


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