Sharepoint authenticates fine on the inside but on the outside forced to change from "Automatic logon only in Intranet Zone"

Outside fails unless on VPN:
Outside Authentication:
Inside Authentication:
Outside Attempts to use the site:
Fiddler from Outside (attempts):
Security Settings (Local Intranet Zone) Site is properly defined in Intranet Zone in GPO:
Please let me know if I can provide any additional information.
Thank you for your assistance in advance!

K BAsked:
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Rainer JeschorCommented:
question: have you extended the web application?
ASP.NET supports only one authentication provider per web application - therefore the normal process is to extend the web app (which creates a second web app) but using the same content as the existing (intranet) web app. Then you configure the zones and authentication settings.

K BAuthor Commented:

Thank you very much for the reply!  
I believe you see can see the web application has been extended in the first two images.
The second zone is the Outside or "Extranet" Zone and the authentication methods is the next image.

Via PowerShell, there does not seem to be a Get-SPWebApplicationExtension command and Get-SPWebApplication | FL does not seem to show much.  If you want me to run a PowerShell command or send additional information/screenshots please do not hesitate to ask.

K BAuthor Commented:
I am realizing that there is only one Claims Based Authentication type being used (WIA / Negotiate)
and only one URL that comes into play (thus only one zone)
So the forms based image above does not come into play.
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Rainer JeschorCommented:
Hi K.B.,
that sounds reasonable (in regards to the behavior).
Can you explain your SharePoint configuration in regards to
- Farm structure (number of Web Frontends, App Server, Database server, (network) load balancer ...)
- Web Applications
- URLs
- Zones and
- Alternate Access mappings?
An intranet/extranet setup with different authentication provider is always tricky - especially when it comes to Kerberos configuration ...

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K BAuthor Commented:

Would you have the PowerShell commands that might be able to provide us the information that you ask?
I cannot be positive.

Thank you
K BAuthor Commented:
2 APPS servers
2 Web servers
1 SQL server
Rainer JeschorCommented:
will have to grab them from my library tomorrow (as its quite late here in Germany). But thanks for the first info.
K BAuthor Commented:
I am awaiting a change request in a couple weeks.. I would like to post results..

removing Forms Authentication from IIS as you see both are enabled in the picture (below)
K BAuthor Commented:
I haven't forgotten about this question.   Waiting on a change window.
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