It turned out to be the certificate... Outlook anywhere does not allow for Subject Alternate Names on certificates like OWA (Outlook Web Access), and OMA (Outlook Mobile Access) do. This company had the same dns name space internally as what they use externally, and registered their certificate to be that of the host name of their old exchange server!!! (yuck). In result I just ignored it and used a subject alternate name that of webmail which they also registered for all services. Bottom line - Outlook Anywhere will not use subject alternative names, only the correct issued to: name of the certificate. I did not find this documented anywhere!
Here is where this is located by default in outlook:
Exchange Autodiscover sets this to msstd:
To get autodiscover to distribute this new one enter in:
Set-OutlookProvider EXPR -Server exch01 -CertPrincipalName "msstd:toph-exchange.restofdomain..."
You only need to set this on the EXPR outlook provider as this is the provider that deals with outlook anywhere.
Please note this is only one fix for when outlook continiously prompts for authentication - there are many causes for this symptom but I documented this one as I have never seen this before nore seen any documentation around this on the internet.