Can't send mail through secure smarthost on 2003

Jordan · Joined: 27 Aug 2007 Posts: 11

I want to configure my Exchange 2003 server to use my ISP's SMTP server as a
smart host. They require a username and password to send SMTP mail and this
is giving me a problem. Here is what I did to setup the smart host and
username password.

Expanded Routing Groups-First Routing Group - Connectors
Right clicked on Internet Mail Connector
Chose Properties
On General Tab I selected "Forwar all mail through...."
Filled in "mail.myispserver.com"
Confirmed that the local server's default SMTP was in the bridgeheads
On the "Advanced Tab" I clicked the Outbound Security button
Changed from Anonymous to Basic Authentication
Clicked Modify
For Username and password I filled in
"admin@myserver.com"
"mypassword"

After doing this all the mail just sits in the queue retrying. When I turn
off the smart host setup the mail goes through fine. What I thought I would
do to make sure my username and password are correct was to telnet in to the
server. Below is the session and it appears the username and password are
correct and that I can send mail.

TELNET Session -----

220 mail.myispserver.com [ConcentricHost ESMTP Relay 2/2.70] ready
ehlo myserver.com
250-mail.myispserver.com
250-PIPELINING
250-SIZE 20971520
250-STARTTLS
250-AUTH PLAIN LOGIN
250-AUTH=PLAIN LOGIN
250-ENHANCEDSTATUSCODES
250 8BITMIME
auth login
334 VXNlcm5hbWU6
{admin@myserver.com in B64}
334 UGFzc3dvcmQ6
{My Password B64}
235 2.0.0 Authentication successful
mail from: admin@myserver.com
250 2.1.0 Ok
rcpt to: someaccount@comcast.net
250 2.1.5 Ok
data
354 End data with .
test.
..
250 2.0.0 Ok: queued as 75D272AC6

Now finally I did another test just as above and used the same login info
and rcpt to info, but I change the mail from info to another user on my mail
server and I was rejected. I thought that if the login name and password
were fine it would not matter what the mail from name is, but it looks like
it does.

Archived from group: microsoft>public>exchange>admin

Jamestechman · Joined: 05 Aug 2007 Posts: 200

This sounds like a setting on the ISPs end. Did you confirm with them
that you are relaying all your users e-mail through your Exchange
server and not your users directly authenticating and relaying to
their SMTP server?

James Chong (MVP)
MCITP | EMA; MCSE | M+, S+, Security+
msexchangetips.blogspot.com

On Feb 27, 3:49 pm, "Jordan" wrote:
> I want to configure my Exchange 2003 server to use my ISP's SMTP server as a
> smart host. They require a username and password to send SMTP mail and this
> is giving me a problem. Here is what I did to setup the smart host and
> username password.
>
> Expanded Routing Groups-First Routing Group - Connectors
> Right clicked on Internet Mail Connector
> Chose Properties
> On General Tab I selected "Forwar all mail through...."
> Filled in "mail.myispserver.com"
> Confirmed that the local server's default SMTP was in the bridgeheads
> On the "Advanced Tab" I clicked the Outbound Security button
> Changed from Anonymous to Basic Authentication
> Clicked Modify
> For Username and password I filled in
> "ad...@myserver.com"
> "mypassword"
>
> After doing this all the mail just sits in the queue retrying. When I turn
> off the smart host setup the mail goes through fine. What I thought I would
> do to make sure my username and password are correct was to telnet in to the
> server. Below is the session and it appears the username and password are
> correct and that I can send mail.
>
> TELNET Session -----
>
> 220 mail.myispserver.com [ConcentricHost ESMTP Relay 2/2.70] ready
> ehlo myserver.com
> 250-mail.myispserver.com
> 250-PIPELINING
> 250-SIZE 20971520
> 250-STARTTLS
> 250-AUTH PLAIN LOGIN
> 250-AUTH=PLAIN LOGIN
> 250-ENHANCEDSTATUSCODES
> 250 8BITMIME
> auth login
> 334 VXNlcm5hbWU6
> {ad...@myserver.com in B64}
> 334 UGFzc3dvcmQ6
> {My Password B64}
> 235 2.0.0 Authentication successful
> mail from: ad...@myserver.com
> 250 2.1.0 Ok
> rcpt to: someacco...@comcast.net
> 250 2.1.5 Ok
> data
> 354 End data with .
> test.
> .
> 250 2.0.0 Ok: queued as 75D272AC6
>
> Now finally I did another test just as above and used the same login info
> and rcpt to info, but I change the mail from info to another user on my mail
> server and I was rejected. I thought that if the login name and password
> were fine it would not matter what the mail from name is, but it looks like
> it does.

Rich Matheisen [MVP] · Joined: 05 Aug 2007 Posts: 797

"Jordan" wrote:

>I want to configure my Exchange 2003 server to use my ISP's SMTP server as a
>smart host. They require a username and password to send SMTP mail and this
>is giving me a problem. Here is what I did to setup the smart host and
>username password.

[ snip ]

>Now finally I did another test just as above and used the same login info
>and rcpt to info, but I change the mail from info to another user on my mail
>server and I was rejected. I thought that if the login name and password
>were fine it would not matter what the mail from name is, but it looks like
>it does.

Talk to your ISP. You're trying to use the SMTP server as a relay for
your server while the ISP is expecting only individual users (probably
POP3/IMAP) to use the relay. The ISP is validating that the person
that authenticated is also the one that's sending the email.

--
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
Don't send mail to this address mailto:h.pott@getronics.com
Or to these, either: mailto:h.pott@pinkroccade.com mailto:melvin.mcphucknuckle@getronics.com mailto:melvin.mcphucknuckle@pinkroccade.com

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