I am in the process of migrating from 2003 to 2010. The mailboxes are moving over fine, and mail is flowing ok between the two. Here is my current configuration External DNSsettings is as follows: mail.domain.com has a dns pointing to my external ip. smtp traffic is still flowing to the 2003 server. web traffic is pointing to 2010. also 443 is flowing to 2010 domain.com is our email domain ie. user@domain.com it uses mail.domain.com as its mx record. smtp traffic is still flowing to the 2003 server. web traffic is pointing to 2010. also 443 is flowing to 2010 email.domain.com redirects to https://email.domain.com (this is so users dont have to type in the https and /owa business This is not set in stone, so if there is a better way to do it let me know pretty please. I may have messed up the initial 2010 setup by typing in email.domain.com rather than mail.domain.com as the external owa address, but it seems to be working ok just the same. When i go to connect with a iphone, it finds the servers and authenticates. the problem is they cant download any mail contacts or anything else. Is this a issue with autodiscover? do i need to create a new subdomain like mobile.domain.com and have it redirect to https://mail.domain.com/microsoft-active-sync any guidance would be greatly appreciated.

Here is another little tid bit. Android phones are syncing perfectly fine. Grrrr

Hi According to your saying, it seems to be iphone problem. Can you offer iphone detail? I will talk with other engineer and post process.Terence Yu TechNet Community Support

I corrected the issue by doing two things. First I added a third party cert. the self signed cert didn't match with the external domain. (email.teamtcs.com). I added that cert and then ran testexchangeconnectivity.com. It gave me a http 500 error. I had to go into my ad account and change the security permissions to inherit from parents. Tested and it worked fine.