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Outlook/Exchange SMPT communication fails over WAN

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jhaudio

IS-IT--Management
Dec 12, 2006
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I know there has to be SOMEONE who has experienced this issue... I hate reposting things, but I looked for hours and can't seem to find the same issue (at least not with resolution).

We are using Exchange 2003 Enterprise. All SMTP communication works fine, most users connect on campus via the exchange connection and everything works great... no problem communication via SMTP to the outside world.

Users can also connect without issues via pop on the internal network... using SPA or not. However, when we try to connect a client to the server from outside it fails to login to the outgoing server. I get the following errors:

"Send test e-mail message: The specified server was found, but there was no response from the server. Please verify that the port and SSL information is correct....etc"

and

"Find outgoing mail server (SMTP): outlook could not connect to the outgoing mail server (SMTP). The problem could be the server name, or port or your server may not support SSL. Verify your port.. etc"

SSL is disabled, and not required (at least not on the internal network).

I have checked the firewall/router, but everything seems fine... port forwarding is forwarding all traffic on 110 and 25 to the server, and NAT is enabled.

I have gone through every SMTP protocol setting that I could find in exchange to see if there was ANYTHING that I could find to try, and I am out of ideas.

Lastly, and this is what is really confusing me, I can connect successfully from a seperate internet connection outside the WAN. We have two internet connections from COX, one which is open for public wireless, and a seperate connection which is behind the firewall and runs mail... I could connect to the public wireless AP on a completely seperate incoming internet connection with the same provider, but still outside our network and it seemed to work fine.

I assume I am probably missing something simple, but if not, is it possible that the ISP is doing something that would allow normal SMTP communcation between servers, but is blocking clients from logging into the exchange server to send mail?

Any help would be greatly apprecciated!
 
Why would you want to connect to mail server externally through a SMTP? It seems unsafe to me and you really should use OWA and publish with a forward server and some type of cert.

if you open the SMTP connection to non domain systems you become a forwarder for spamers.

Capt Mike
 
I agree... we do use OWA for almost everybody in the company. The issue is that our CEO does not want to use OWA, and instead wants to (continue) use Outlook or Outlook Express so that he can recieve his other 4 e-mail addresses together externally.

I would really like to find a way to tunnel exchange connectivity to laptops via the web while they are off campus.

Thanks for your response! Any additional information, or a suggested path to a better resolution would be very very helpful.
 
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