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I am trying to give some of my users who can't connect to our VPN on certain sites the ability to access our SharePoint 2013 sites from anywhere via the internet.

Our internal SharePoint runs over HTTPS for added functionality with syncing tasks and calendars ect. and internally uses a SELF SIGNED SSL certificate.

I have setup so far, my web listener, reverse proxy and DNS records, when I type the URL in on the internet I can hit the TMG credentials page but then it returns a Page 500 error after.

my settings are explained below.

---------Network-----------

External DNS (A) record called "share2013" pointing to a external IP address we have - 86.188.184.122

Internal DNS (A) record called "share2013" pointing to the internal SharePoint - 192.168.254.159

We have a NAT rule on our firewall that NATS traffic to our TMG web listener on our DMZ- 86.188.184.122 - 192.168.113.122

The web-listener is configured with SSL and has a certificate from go daddy to prevent cert errors for external traffic.

When configuring the web-listener I told it to use HTTP for internal communication, is this incorrect due to the fact that the SharePoint server is using SSL certs? i have tried selecting HTTPS but this didn't seem to work either.

The internal SharePoint name is sharepoint2013.intneraldomain.co.uk and the external web listener is configured for share2013.externaldomain.com which has also been added into SharePoint alternative access mapping.

The IIS bindings has a cert and HTTPS port already existing for the SharePoint internal site that uses the self-signed certificate so I can’t add the go daddy cert because the names don’t match up (if I even need to?).

When looking the in the ULS records when someone try’s to connect the error pops up saying

An exception occurred when trying to issue security token: The server was unable to process the request due to an internal error. For more information about the error, either turn on IncludeExceptionDetailInFaults (either from ServiceBehaviorAttribute or from the configuration behavior) on the server in order to send the exception information back to the client, or turn on tracing as per the Microsoft .NET Framework SDK documentation and inspect the server trace logs..

Is extending the web application something I need to do? Because when I press extend web application it returns the error

The web application could not be extended because an unused zone could not be found. Unextend the web application from the zone that you intend to use for the new IIS web site before performing this operation.

Any ideas I am totally stuck at this point.

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Most likely the problem is with STS service, did you set up and is it running properly, there are few steps you might to take described in this blog for you.

SharePoint 2010: Nailing the error "The Security Token Service is unavailable"

There are steps involving exploring service's application in IIS and restarting service etc.

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