How to extend a SharePoint site

Current Config:
- 1x front end SharePoint (SP) server
- 1x back end SP server (i.e. houses the content databases)
- 2x SP web applications
- no DMZ

I need to Extend one of our two SP web applications to our partner companies and clients across via the Internet. I don't have the capital to install an additional front end SP server and I do not want to configure a DMZ. Right now the two SP web applications are accessible on port 80 using hostheaders.

From what I can tell it seems like I can do the Extend... wizard using the same URL but specifying SSL to force the Extension site onto port 443. Since the socket will be different I would assume the site would be accessible internally via http:// and https:// using the same URL. However, I've tried doing this and the site is still only accessible via http://... not https:// when hitting it internally. Before I NAT over 443 I'd like to see this work internally first. Please help!
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Did you install a test certificate on the server internally?
What are your Alternate Acces Mapping Settings configured like?

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iVenture_SolutionsAuthor Commented:
Thank you for the suggestion. The missing cert was the issue; we were waiting to straighten out an issue with the CA and didn't have it yet.
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