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RDWEB and DNS troubles, Internal vs. External

Wondering is someone can assist.

I have deployed a new RDWEB setup using Windows Server 2012R2.  I have all certificates in place, using a wildcard cert, all DNS entries as well.

The site works great internally and externally, except if I try to use a domain joined system externally.

I believe my issue is related to our internal domain name is the same as the external domain name.

I have setup external DNS: demo.mydomain.com point to external IP  of RD gateway

I have setup internal DNS: demo.mydomain.com points to internal IP of RD gateway.

Again, I can access the site and all published apps fine from public computers, and even my tablet.  The issue is only when I use a domain joined system, like my laptop, that I take off-site.

I can get to the RDWEB site, log in, and see all the published apps. When I click on an app, it tries to connect, and seems to time out and give this error:

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 network support.

Any help is appreciated.

Steve


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