MS's IIS - SMTP outgoing email fails

Discussion in 'Computer Support' started by Agent 008:, Oct 3, 2003.

  1. Agent 008:

    Agent 008: Guest


    I have a specific web service on the Internet which requires to send
    an email out to Internet email addresses. I have installed IIS SMTP
    service on the same W2K server hoping that it would "relay" the SMTP
    email created on the web application out to the Internet destinined
    for the recipient. Unfortunately this is failing to send anything out.

    The single server is located on a DMZ and has access rules though the
    firewall and router permitting outward DNS & SMTP and inward HTTP &
    HTTPS connections.

    The web service (not IIS) is fully accessible. I can use nslookup on
    the server to query external DNS servers to get MX addresses from
    domains. I can also Telnet to these addresses on port 25(SMTP) and
    then manually craft a valid external email which is delivered. So I
    am happy that the router/firewall configurations are working fine.

    If I use Outlook on the same server to create an email, sending it to
    the IIS service on the same server, it is accepted and Outlook is
    happy. However the email simply remains in the IIS SMTP QUEUE
    folder, and after a while some non-delivery warnings appear in the
    queue. I don't want any inward SMTP from the Internet to arrive at
    this server, and all non-delivery notifications etc. are to be sent to
    another IP domain via another Internet connection which has a fully
    working in and out SMTP service.

    I was hoping that IIS's SMTP service would do the external MX lookup
    and establish a direct SMTP connection with the recipients IP domain
    mail server(s), but it' not :( I did try setting up a "REMOTE
    domain" in IIS for * but test emails to this domain were still

    I know there is an option to specify a "smart host" to relay SMTP
    emails to, but I don't want to pass this to an external SMPT relay and
    I would prefer that this single server was a "smart host" and actually
    sent the email.


    1. can IIS SMTP server take SMTP email from an application the same
    server and then connect directl;y out to the Internet to send it on to
    the recipient's mail server ?

    2. If it can; can anyone got any ideas what may be wrong, or
    anything I should be checking ? (The logs only show the SMTP service
    accepting the emails but no sign of any attempts to send it)

    3. If IIS can't do this: can anyone suggest a simple product that
    could ?

    Agent 008:, Oct 3, 2003
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  2. Agent 008:

    °Mike° Guest

    Smells like spam...

    °Mike°, Oct 3, 2003
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  3. Agent 008:

    Agent 008: Guest

    Nope ! Spam has a smokey spicy ham smell

    I have a SMTP server at home POSTCAST, but my employer insists on
    using IIS and I can't get it to work :(

    Everything works as it should DNS and SMTP port 25, just IIS doesn't
    do anything useful.

    Agent 008:, Oct 4, 2003
  4. Agent 008:

    °Mike° Guest

    Well, forgive me, but when I see the words "specific service", "SMTP"
    and "relay" in the same sentence, that rings alarm bells.
    °Mike°, Oct 4, 2003
  5. Agent 008:

    Agent 008: Guest

    The "specific service" is a public facing web service for online
    auctions - not a "live auction", but a simple sealed bids system. The
    system is a purchased "complete package" that assumes access to a
    SMTP service which there is none on this Internet connection, and I
    don't want to bring the email "inside" to process through our
    corporate email severs which are required to be kept secure and
    isolated from all but a few selected trusted systems.

    I intend to put a packet sniifer on the link on Moday to see what is
    or is not going out, but I'm impatient and thought I'd try a posting
    to see if anyone knew any obvious setup problem with IIS's SMPT

    Open to all sensible suggestions.

    Agent 008:, Oct 4, 2003
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