This is the current setup: F5 Load Balancer (VIP IP Addresses) outlook.company.com ....10.16.12.218 mail.company.com .......10.16.12.217 autodiscover............10.16.12.217 Outlook.company.com is the RpcClientAccessArray name set on all databases. The FQDN of the F5 is The Certificate on both Hub/Cas servers has CN=mail.company.com, SAN names of mail.company.com, autodiscover.company.com, webmail.company.com The same certificate has been added to the F5 load balancer. Both Hub/Cas servers have the AutodiscoverServiceInternalUri set to https://autodiscover.company.com/autodiscover/autodiscover.xml. I understand that this needs to match the FQDN of the F5 load balancer. All of the other web services have both the Internal and External Urls set to https://mail.company.com/etc... When I open Outlook, should it not auto-populate the email address and e-mail settings and autoconfigure the account for Exchange? Instead, I get prompted for credentials but it never takes the username/password.

When I test Autodiscover in Outlook, it reads: Autoconfiguration was unable to determine your settings! Now, if Sites & Subnets are not set correctly, this could cause the behavior, correct? They have a ssite called XXX and the subnet associated with it is 10.16.0.0/16. However, the domain controllers and Exchange servers are on 10.16.4.0/24 and 10.16.6.0/24 and the F5 device is on 10.16.12.0/24. Do we need to add those subnets to Sites and Services and associate them with Site XXX?

The cas array name is Outlook.company.com. Does that also need to be added to the certificate?