troubleshooting Question

Cannot get IMAP on iPhone 3GS with Exchange 2007 / Forefront TMG to work

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axeon78Flag for Switzerland asked on
ExchangeMicrosoft Forefront ISA ServeriPhone
5 Comments1 Solution1711 ViewsLast Modified:
Dear all,
It would really be great if some of you guys could help me with this issue - I already spent hours and hours on this problem without being able to finally solve it. The intention itself is rather simple: we are using the Microsoft Essential Business Server 2008 with Exchange 2007 and Forefront TMG. Based on the MS Exchange IMAP protocol, we would like to sync the iPhone 3GS with the mailboxes on MS Exchange. Unfortunately we cannot use Active Sync as this is in use for another account already).

So far so good. We opened the ports 143 and 993 on the Firewall and published the "IMAP4 Server"  and the "IMAPS Server" protocols on Forefront, pointing to the MS Exchange server. We did not yet setup SMTP - I would assume that this is not really an issue until we don't want to send e-mails from the iPhone...

When everything has been setup, I  configured the iPhone. As I was not able to connect to the IMAP mailbox on the Exchange server, I decided to first test the IMAP configuration on the Exchange server itself. On the iPhone, I configured the internal address of the Exchange server and connected via internal WLAN. The synchronization was successful with (143) and without SSL (993). So the configuration (including settings on the iPhone like username, password etc.) on the Exchange side should be ok and valid.

When I switch to the external Address, I am unable to sync, although the ports 143 & 993 have been forwarded to the Exchange server. The error message I get on the iPhone is: "Cannot get Mail. the connection to the server failed."

I started the monitoring on the ISA server and found some interesting entries which appear whenever I try to connect, where is the IP of the Exchange Server and is the IP of Forefront's external Interface pointing to the Firewall: -> -> 143 -> IMAP4 Server ->Initiated Connection: 0x0 ERROR_SUCCESS -> -> 143 -> IMAP4 Server -> Closed Connection: 0x80074e21 FWX_E_ABORTIVE_SHUTDOWN -> -> 143 -> IMAP4 ->Denied Connection: 0xc0040017 FWX_E_TCP_NOT_SYN_PACKET_DROPPED      

Why do I get a message like "abortive shutdown" - if the protocol has been published to the Exchange server? And: why is there another connection opened to the external interface of Forefront (

A made another observation, maybe this helps: I have set-up Mozilla Thunderbird and was able to connect from outside via IMAP to my mailbox via SSL / port 993. Interesting is: if I enable "use secure authentication" the connection fails with the message " have enabled secure authentication and this server does not support it."
When I disable Thunderbird and try to connect without SSL, the connection is not successful as well.

I would really appreciate if you could help me further with this issue!

Thank you,
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