Status 12030 The connection with the server was terminated abnormally.

I have a weird issue. I'm trying to move over an IIS 6.0 website to IIS 8.5.

We want to use TMG to allow external for security.

Before the official move, I created a new DNS for testing.

Original DNS: original.test.com - this points to IIS 6.0 server
New DNS: new.test.com - this points to the IIS 8.5 server

On TMG I created a rule to allow connections to new.test.com using a wildcard SSL certificate for the test. When I test the rule it passes. I can access the website internally and externally, but further testing of the website from the homepage cannot be done because the links are hardcoded to the original DNS. I didn't think that mattered since the rule passed.

I went ahead and began pointing original.test.com to the new IIS 8.5 server. I modify both external and internal DNS entries. I modify the TMG rule from new.test.com to original.test.com. I run the rule, it fails.

Internally, I can access the website perfectly fine.
Externally, I can get to the website's homepage, but going further, I get a Status 12030 The connection with the server was terminated abnormally.

TMG 2010 has SP2.

Anyone have any ideas what I should look at? I'm confused.