I have an Exchange 2007 SP1 Rollup 8 server that houses all of the roles. The OS is Server 2008. I have two Web Sites in IIS with two certificates. The first certificate bound to the Default Web Site is a self signed certificate with the internal server name (Server-Name.InternalDomain.com). The certificate bound to the second web site is a third party certificate with the outside domain name (Mail.Domain.com). Due to the internal domain being owned externally by another company a Unified Communications Certificate is not possible. The server was migrated from a 2003 server where their were two web sites in IIS. The additional Web Site held the Rpc, RpcWithCert, and OWA virtual directories with the third party cert bound to its address while the Default Web Site housed the rest with Self Signed Certificate bound to it. I cannot get Outlook Anywhere to point to the second web site. I also recreated the OWA virtual Directories on the second web site but Exchange still looks to the Default Web Site. The main goal of this is of course to make it so their are no certificate warnings for internal, OWA, or Outlook Anywhere users.