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IIS 6.0 SMTP Virtual Server Outbound relaying RRS feed

  • Question

  • Hi All,

    I am very new to SMTP and setting up the SMTP Virtual server. I hope this is the correct forum for the Virtual Server. I have following various configurations listed in TechNet. I have a Virtual Server that is working but it seems to working incorrectly. I will explain my how my server is configured.

    The SMTP is configured to accept SMTP from specific IPs listed under Access>Relay. The configuration under Access>Connection is set for "all except list below"

    I have set authentication to "Basic Authentication".

    I have nto configured any remote domains.

    With this setup, I am able to send SMTP messages to the relay and the relay sends the message out to the remote Mail Servers. But when I look at the logs, it is sending it to the destination's Mail Server and not the sender's mail server. When I attempt to send a message to the same domain as the sender, it does not send it out.

    My understanding is that the SMTP Relay function is suppose to send the mail to the sender's Mail Server then that Mail server will continue to send the message to its final destination.

    Please any help is greatly appreciated. Please let me know if you require more information or if my understanding of a SMTP Relay is wrong.

    Thanks

    • Moved by Zi Feng Monday, May 6, 2013 6:49 AM
    Friday, May 3, 2013 8:09 PM

Answers

  • On Fri, 3 May 2013 20:09:19 +0000, adurf wrote:
     
    >I am very new to SMTP and setting up the SMTP Virtual server. I hope this is the correct forum for the Virtual Server.
     
    It isn't the correct forum. You should probably be posting your
    question in a forum for your O/S or IIS.
     
    >I have following various configurations listed in TechNet. I have a Virtual Server that is working but it seems to working incorrectly. I will explain my how my server is configured.
    >
    >The SMTP is configured to accept SMTP from specific IPs listed under Access>Relay. The configuration under Access>Connection is set for "all except list below"
    >
    >I have set authentication to "Basic Authentication".
    >
    >I have nto configured any remote domains.
    >
    >With this setup, I am able to send SMTP messages to the relay and the relay sends the message out to the remote Mail Servers.
     
    That looks like it's doing what it's supposed to do.
     
    >But when I look at the logs, it is sending it to the destination's Mail Server and not the sender's mail server.
     
    Why would you want the email to go to the sender and not the
    recipient???
     
    >When I attempt to send a message to the same domain as the sender, it does not send it out.
     
    Is that because you have the domain configured as a loccal domain? If
    that's true then the server is putting the messages into the "Drop"
    directory.
     
    >My understanding is that the SMTP Relay function is suppose to send the mail to the sender's Mail Server then that Mail server will continue to send the message to its final destination.
     
    A relay server, unless it's configured to send its outbound messages
    to a smart host will use DNS to locate an appropriate server in the
    recipient's domain and then transfer the message there. I'm going to
    guess that you want your relay server to send it to some other server
    within your organization, and then that server will deliver the
    message to the recipient's domain? If that's true then you have to
    configure the SMTP VS to use a smart host.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by adurf Monday, May 6, 2013 7:24 PM
    Saturday, May 4, 2013 5:13 PM
  • On Mon, 6 May 2013 13:03:30 +0000, adurf wrote:
     
    >
    >
    >Thanks for the Reply Rich. And thanks to Zi Feng for moving this post to the correct Forum!
    >
    >The issue was seeing when an email was sent to the same domain was describe incorrectly above. The message is sent out from the SMTP relay but it never arrives in the user's inbox. I believe that issue resides from the recipients mail server.
    >
    >I was asked to create a SMTP relay that would forward SMTP to the sender's Mail Server which would handle the delivery of the message to the recipient. I thought it was be similar to a web proxy.
     
    I still think you have your terminology backwards. SMTP delivers
    e-mail to a recipent, not to a sender. If sender "A" sends a mail to
    recipient "B" you want the mail to go to the e-mail system of "B".
     
    >From the way this is being explained, it is not possible to proxy the communication between the recipient and the recipient's Mail Server (i.e. gmail user and gmail servers)
    >
    >I am going to attempt to add a smart host to see if this will clear up any issues.
     
    If you want your SMTP relay server to deliver email to the recipient's
    e-mail system then you should probably just let it use DNS to find the
    mail exchanger for the other domain and deliver it directly.
     
    SMTP is store-and-forward system, not a proxy.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Zi Feng Friday, May 10, 2013 1:36 AM
    Tuesday, May 7, 2013 3:09 AM

All replies

  • On Fri, 3 May 2013 20:09:19 +0000, adurf wrote:
     
    >I am very new to SMTP and setting up the SMTP Virtual server. I hope this is the correct forum for the Virtual Server.
     
    It isn't the correct forum. You should probably be posting your
    question in a forum for your O/S or IIS.
     
    >I have following various configurations listed in TechNet. I have a Virtual Server that is working but it seems to working incorrectly. I will explain my how my server is configured.
    >
    >The SMTP is configured to accept SMTP from specific IPs listed under Access>Relay. The configuration under Access>Connection is set for "all except list below"
    >
    >I have set authentication to "Basic Authentication".
    >
    >I have nto configured any remote domains.
    >
    >With this setup, I am able to send SMTP messages to the relay and the relay sends the message out to the remote Mail Servers.
     
    That looks like it's doing what it's supposed to do.
     
    >But when I look at the logs, it is sending it to the destination's Mail Server and not the sender's mail server.
     
    Why would you want the email to go to the sender and not the
    recipient???
     
    >When I attempt to send a message to the same domain as the sender, it does not send it out.
     
    Is that because you have the domain configured as a loccal domain? If
    that's true then the server is putting the messages into the "Drop"
    directory.
     
    >My understanding is that the SMTP Relay function is suppose to send the mail to the sender's Mail Server then that Mail server will continue to send the message to its final destination.
     
    A relay server, unless it's configured to send its outbound messages
    to a smart host will use DNS to locate an appropriate server in the
    recipient's domain and then transfer the message there. I'm going to
    guess that you want your relay server to send it to some other server
    within your organization, and then that server will deliver the
    message to the recipient's domain? If that's true then you have to
    configure the SMTP VS to use a smart host.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by adurf Monday, May 6, 2013 7:24 PM
    Saturday, May 4, 2013 5:13 PM
  • Thanks for the Reply Rich. And thanks to Zi Feng for moving this post to the correct Forum!

    The issue was seeing when an email was sent to the same domain was describe incorrectly above. The message is sent out from the SMTP relay but it never arrives in the user's inbox. I believe that issue resides from the recipients mail server.

    I was asked to create a SMTP relay that would forward SMTP to the sender's Mail Server which would handle the delivery of the message to the recipient. I thought it was be similar to a web proxy.

    From the way this is being explained, it is not possible to proxy the communication between the recipient and the recipient's Mail Server (i.e. gmail user and gmail servers)

    I am going to attempt to add a smart host to see if this will clear up any issues.

    Monday, May 6, 2013 1:03 PM
  • On Mon, 6 May 2013 13:03:30 +0000, adurf wrote:
     
    >
    >
    >Thanks for the Reply Rich. And thanks to Zi Feng for moving this post to the correct Forum!
    >
    >The issue was seeing when an email was sent to the same domain was describe incorrectly above. The message is sent out from the SMTP relay but it never arrives in the user's inbox. I believe that issue resides from the recipients mail server.
    >
    >I was asked to create a SMTP relay that would forward SMTP to the sender's Mail Server which would handle the delivery of the message to the recipient. I thought it was be similar to a web proxy.
     
    I still think you have your terminology backwards. SMTP delivers
    e-mail to a recipent, not to a sender. If sender "A" sends a mail to
    recipient "B" you want the mail to go to the e-mail system of "B".
     
    >From the way this is being explained, it is not possible to proxy the communication between the recipient and the recipient's Mail Server (i.e. gmail user and gmail servers)
    >
    >I am going to attempt to add a smart host to see if this will clear up any issues.
     
    If you want your SMTP relay server to deliver email to the recipient's
    e-mail system then you should probably just let it use DNS to find the
    mail exchanger for the other domain and deliver it directly.
     
    SMTP is store-and-forward system, not a proxy.
     
    ---
    Rich Matheisen
    MCSE+I, Exchange MVP
     

    --- Rich Matheisen MCSE+I, Exchange MVP
    • Marked as answer by Zi Feng Friday, May 10, 2013 1:36 AM
    Tuesday, May 7, 2013 3:09 AM