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I am having some issues getting our SfB server running when connected outside the company network.

We have a standalone SfB server with a hostname: hostname.domain.local

The SIP domain looks like this: domain.co.uk

When connected internally, our users can message each other without issues, but cannot reach any external users.

When connected externally, our users cannot sign in.

Using an external CA certificate on Web services External and a local CA certificate on Web services internal gets the following using Microsoft Remote Connectivity Analyzer:
Host name sipexternal.domain.co.uk doesn't match any name found on the server certificate CN=hostname.domain.local

Using a local CA certificate on both internal and external Web services, I get an error about being unable to build a certificate chain on Microsoft Remote Connectivity Analyzer.

Is there a way to configure our internal DNS to resolve the correct details?

FryFubar
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  • How close are you to being able to fix your domain's name? – Michael Hampton Jan 25 '19 at 15:25
  • @MichaelHampton Sorry, I'm not sure I follow. Could you clarify? – FryFubar Jan 25 '19 at 15:28
  • You are going to have to rename your Windows domain, because whoever set it up didn't set the name according to [best practices](https://serverfault.com/q/76715/126632). There might not be any other solution here. – Michael Hampton Jan 25 '19 at 15:31
  • I see what you mean now. Unfortunately, I've inherited the network with a .local domain, which isn't ideal. But that's what I've got to work with and I won't be changing it anytime soon. The scope of such a project, just to get Skype on-prem working, would be too great. – FryFubar Jan 25 '19 at 15:54
  • From what I can see, SfB server creates two IIS sites: one for internal and the other for external services. The internal ports are bound to port 80 and 443 for http and https respectively. The external ports are bound to 8080 and 4443. I've tried using port forwarding on our firewall to redirect the external ports 80 and 443 to the SfB server's private IP on ports 8080 and 4443. No luck. – FryFubar Jan 25 '19 at 16:25

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