When setting up the external domain with the SBS 2008 / 2011 wizard it setups up the domain with one a record (remote.domain.com)
This is well and good, but it has a downside which is worth knowing that you have to set up a SRV record for the domain so that Autodiscover will work properly for external client auto-configuration.
This is because you are using a single-name SSL certificate, which isn’t what Exchange 2007/2010 was designed to use.
So to solve this issue you need create an Autodiscover SRV record so that Outlook 2007 on-wards to auto-configure for Outlook Anywhere (RPC-over-HTTPS) and ActiveSync and also not give an annoying SSL warning.
The Microsoft KB is – KB940881 but here are the steps I use.
- Remove any autodiscover and “*” A records for the domain
- Add the SRV record for
- Hostname = _autodiscover._tcp
- Priority = 1
- Weight = 1
- Port = 443
- Target = remote.domain.com