We have an Exchange 2010 environment running behind an ASA 5510 and I have a weird iPhone (& iPad) connection issue to ActiveSync. When the exchange account is initially added, it says "The Connection to the Server Failed" and after 20 seconds, it finally works. Once it connects it is fine and works as any other exchange account I have used works. I can't for the life of me figure out what is wrong. I have looked for a redirect issue in IIS7, but I can't seem to find anything. I have also checked my firewall but all traffic seems to be going to port 443. This happens with every iDevice I have tried on WiFi and 3G.
The iPhone/iPad makes the connection, and then there is a 20 second delay where there is no traffic between the devices. It might be a delay between activesync and the global catalog.
It does not matter if the iphone is on 3G or wifi. iPad is only WiFi
I placed Wireshark on a mirrored port to monitor all traffic going to the exchange server. There is a 20 second gap from the last packet sent from the first handshake
10.157.20.7 is the server and 10.157.10.34 is the iPad.
397 29.877418 10.157.20.7 10.157.10.34 TCP 66 https > 49572 [ACK] Seq=791 Ack=1227 Win=65536 Len=0 TSval=4492670 TSecr=731525178
and the next two packets are: (after the 20 second gap, if you look at the timestamp)
627 49.870330 10.157.20.7 10.157.10.34 TLSv1 391 Application Data
628 49.968606 10.157.10.34 10.157.20.7 TCP 66 49572 > https [ACK] Seq=1227 Ack=1116 Win=130736 Len=0 TSval=731545189 TSecr=4494670
I am completely stumped and I think it is something simple I am missing.Thank you!