To get autodiscover to distribute this new one enter in: however in our case its toph-exchange.domain. Here is where this is located by default in outlook:Įxchange Autodiscover sets this to msstd: which is in this case webmail.domain. Bottom line - Outlook Anywhere will not use subject alternative names, only the correct issued to: name of the certificate. In result I just ignored it and used a subject alternate name that of webmail which they also registered for all services. 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). Outlook anywhere does not allow for Subject Alternate Names on certificates like OWA (Outlook Web Access), and OMA (Outlook Mobile Access) do. They would enter their credentials, then it would just reprompt them for login. I came accross this case where outlook kept prompting for login every time a user tried to login to outlook via outlook anywhere.
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