SBS 2008 EXCHANGE 2007 IMAP CONNECTION PROBLEMS

Aelara
Aelara used Ask the Experts™
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Hello, The sbs 2008 exchange setup allows me to send and receive smtp emails via Outlook on the domain or using the Outlook Web Access facility. The problem lies with external IMAP connections to the exchange server. I can get Outlook whilst on the move to connect and pull contents of the email folders but I am unable to send via IMAP. The same applies to my handheld device, Incoming OK, Outgoing not happening. All relevant ports on the firewall are open and forwarding to the server eg, 25,143,587,993.

Been through the exchange management consol and within IMAP4 properties set the x509 certificate to remote.domain.co.uk and use a secure logon (TLS connection)

In outlook new account settings, Incoming is set to domain.co.uk and outgoing to remote.domain.co.uk. For outgoing authentication is set to same as incoming.

The Exchange IMAP service is running, I have tried several combinations of ports on the Clients using Outlook 2010, Entourage 2008 on a Mac and my HTC handheld. All connect to the inbox and update emails as they arrive but nothing goes out. Error message from Outlook is:

Task 'myname@domain.co.uk - Sending' reported error (0x80042109) : 'Outlook cannot connect to your outgoing (SMTP) e-mail server. If you continue to receive this message, contact your server administrator or Internet service provider (ISP).

Any ideas? Many Thanks.
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Rick FeeMessaging Engineer - Disaster Recovery Engineer

Commented:
First just make sure you have connectivity which you probably already attempted.   From the client in the field when attempting to IMAP run a command line:
telnet remote.domain.co.uk 25    do you get a banner?

Author

Commented:
Hello, If I execute the command all I get is "Could not open connection to the host on port 25: Connection failed.

If I execcute the command telnet domain.co.uk 25 (Omitting remote.) it tells me the Mail service is ready.

SBS 2008 creates remote. during internet name wizard and seems key to the setup. As mentioned before outgoing email is ok.

Thanks.

Author

Commented:
Sorry, meant to say incoming mail is ok, Outgoing is the problem.
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Rick FeeMessaging Engineer - Disaster Recovery Engineer

Commented:
Ok I was confused there...and your outgoing is remote.domain.co.uk this is your problem...SMTP is not open for remote.domain.co.uk, which is not allowing you to send.
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Rick FeeMessaging Engineer - Disaster Recovery Engineer

Commented:
If you set your outgoing to domain.co.uk can you send?    

Author

Commented:
No, That was my first thought, Everything seems in place, Just missing something.
Rick FeeMessaging Engineer - Disaster Recovery Engineer

Commented:
Ok but the result you want is to be able to send email out using remote.domain.co.uk
So your firewall is does not have a NAT for 25 to the mail server for remote.domain.co.uk
Why are you using two FQDN's that appear to be going to one server?
Next question are you checking in Outlook:  My Outgoing server requires authentication?   This would be for domain.co.uk

Author

Commented:
Thanks, I'm following instructions based on the SBS 2008 wizards. The box is ticked in Authentication and is set to same as incoming.

If is set incoming to remote.domain.co.uk then I also loose the ability to receive mail.

Hope this helps.
Messaging Engineer - Disaster Recovery Engineer
Commented:
Is remote.domain.co.uk  and domain.co.uk the same IP...and both are accessible externally?

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