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Send All Messages Using External SMTP Server - 12.Jun.2008 3:10:17 PM

Kirk

Posts: 6
Joined: 3.Apr.2006
Status: offline

Hi All,

I'm new to Exchange 2007 and I am trying to configure the system to send all outbound messages using my external SMTP server hosted by a shared web hosting provider. I looked into send connectors but I'm not sure if my SMTP server, mail.kirkouimet.com, qualifies as a smart host.

Is it possible to have Exchange send all messages using my external, third party, SMTP server?

Mail flow would ideally go like this:

Exchange > mail.kirkouimet.com > External Destination E-mail Address

Any help in this would be much appreciated.

Thanks!

Kirk Ouimet

Post #: 1

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RE: Send All Messages Using External SMTP Server - 12.Jun.2008 5:19:30 PM

John Weber

Posts: 588
Joined: 20.Apr.2005
From: Portland, Oregon
Status: offline

smarthost it is.

_____________________________

-jmw
http://tsoorad.blogspot.com

(in reply to Kirk)

Post #: 2

RE: Send All Messages Using External SMTP Server - 12.Jun.2008 5:51:10 PM

Kirk

Posts: 6
Joined: 3.Apr.2006
Status: offline

Thanks for the reply John.

I added mail.kirkouimet.com as a new connector. For kicks I tried no authentication and I actually got a message back from Exchange! It says:

Diagnostic information for administrators:

Generating server: home.local

madmax.dreamhost.com #554 Service unavailable; Client host [myIP] blocked using zen.dnsbl; http://www.spamhaus.org/query/bl?ip=myIP ##

So it looks like I'm getting filtered by DreamHost's (my hosting service) spam filter. When I try to use Basic Authentication with my user name and password (with or without TLS checked) I don't get any response in anyway - the message isn't delivered and Exchange doesn't respond. Is it possible to see if the messages are stuck in some kind of queue?

< Message edited by Kirk -- 12.Jun.2008 5:53:18 PM >

(in reply to John Weber)

Post #: 3

RE: Send All Messages Using External SMTP Server - 12.Jun.2008 6:01:03 PM

Sembee

Posts: 3583
Joined: 17.Jan.2008
From: Somewhere near London, UK
Status: offline

Have you asked your host if you can relay email through their server? Not all hosts will allow it. They also may have a different server for email to relay through. If you are blacklisted and the host is using blacklists to filter spam then your anonymous message was what I would expect to see. It has blocked your message like any other message being delivered to its servers.

Your first call needs to be the host.
You could also try routing email through your ISPs SMTP Server.

There is a queue viewer in Exchange 2007. It is part of the Toolbox, but can also be put in to a new MMC session separately.

Simon.

_____________________________

Simon Butler,
Exchange MVP
Blog: http://www.sembee.co.uk/
Web: http://www.amset.info/
In the UK? Hire me: http://www.amset.co.uk/

(in reply to Kirk)

Post #: 4

RE: Send All Messages Using External SMTP Server - 12.Jun.2008 6:42:41 PM

Kirk

Posts: 6
Joined: 3.Apr.2006
Status: offline

Thanks for your response Sembee.

I just e-mailed my host. I took a look at the queue viewer and here is what I am seeing:

I tried using "Basic Authentication." I received this error message in my Exchange message queue:

*********
"451 5.7.3 Require basic authentication." Attempted failover to alternate host, but that did no succeed.
*********

I tried using "Basic Authentication over TLS" and received this error in my Exchange message queue:

*********
"451 5.7.3 Require STARTTLS to do basic authentication." Attempted failover to alternate host, but that did no succeed.
*********

Any ideas on those errors?

Thanks so much!

(in reply to Sembee)

Post #: 5

RE: Send All Messages Using External SMTP Server - 12.Jun.2008 7:20:21 PM

Kirk

Posts: 6
Joined: 3.Apr.2006
Status: offline

SOLUTION FOUND:

Turns out that DreamHost does not allow message relaying through their customer's SMTP servers. I used my ISPs SMTP server and it worked fine.

Thanks!

(in reply to Kirk)

Post #: 6