Windows Vista Forums

advise on smtp service (windows 2003 SP2)

  1. #1


    pheonix1t Guest

    advise on smtp service (windows 2003 SP2)

    hello,
    I'm trying to get smtp service on 2003 server to let me relay from
    port 25 to gmail (smtp port 465 via SSL or TLS).
    I've configured the settings to outgoing = smtp.gmail.com, smtp port
    is set to 465 and TLS is selected.
    It accepts emails but they get stuck in the queue folder. The don't
    leave.

    What else can I check or configure? The logging on this is minimal
    at best. Not much help in troubleshooting where it's not working!!

    Thank you,

    Oskar

    ps. My goal is to allow older network equipment (copiers/scanners and
    some desktop software) to send email out from port 25. We are on an
    ATT circuit and they have closed port 25 completely. The idea is
    internally the smtp service accepts smtp connections via port 25 but
    then relays it via google gmail to the outside world via port 465 with
    encryption!


      My System SpecsSystem Spec

  2. #2


    neo Guest

    Re: advise on smtp service (windows 2003 SP2)

    Not only do you have to worry about the port and SSL/TLS, but did you
    configure outbound security to supply your g-mail credentials?

    <pheonix1t@newsgroup> wrote in message
    news:d569c12c-5ea8-4b9c-8fc5-ad531c23003a@newsgroup

    > hello,
    > I'm trying to get smtp service on 2003 server to let me relay from
    > port 25 to gmail (smtp port 465 via SSL or TLS).
    > I've configured the settings to outgoing = smtp.gmail.com, smtp port
    > is set to 465 and TLS is selected.
    > It accepts emails but they get stuck in the queue folder. The don't
    > leave.
    >
    > What else can I check or configure? The logging on this is minimal
    > at best. Not much help in troubleshooting where it's not working!!
    >
    > Thank you,
    >
    > Oskar
    >
    > ps. My goal is to allow older network equipment (copiers/scanners and
    > some desktop software) to send email out from port 25. We are on an
    > ATT circuit and they have closed port 25 completely. The idea is
    > internally the smtp service accepts smtp connections via port 25 but
    > then relays it via google gmail to the outside world via port 465 with
    > encryption!
    >

      My System SpecsSystem Spec

  3. #3


    pheonix1t Guest

    Re: advise on smtp service (windows 2003 SP2)

    Yes, I did that too.
    The logging is primitive on this but I did see on the event logs
    (system) that it connects to me.com but that server won't accept the
    connection. What I'm wondering about is plenty of email servers (in
    public internet) now run strict RFC adherence. I can only wonder what
    this server looks like for valid host name, reverse DNS, valid helo
    greeting, etc.

    Maybe it's failing one or more RFC checks? Windows servers aren't
    famous for adhering to RFC rules but lots of Linux mail servers are
    VERY strict about RFC rules. I've seen lots of companies that use
    gateway SMTP servers (usually linux machines) for email to run spam/
    virus filtering. Internally they have exchange/lotus/groupwise.
    Lately you can outsource this service to google or similar (Postini).

    Thanks,

    Oskar


    On Apr 28, 6:38*am, "neo" <n...@newsgroup> wrote:

    > Not only do you have to worry about the port and SSL/TLS, but did you
    > configure outbound security to supply your g-mail credentials?
    >
    > <pheoni...@newsgroup> wrote in message
    >
    > news:d569c12c-5ea8-4b9c-8fc5-ad531c23003a@newsgroup
    >

    > > hello,
    > > I'm trying to get smtp service on 2003 server to let me relay from
    > > port 25 to gmail (smtp port 465 via SSL or TLS).
    > > I've configured the settings to outgoing = smtp.gmail.com, smtp port
    > > is set to 465 and TLS is selected.
    > > It accepts emails but they get stuck in the queue folder. *The don't
    > > leave.
    >

    > > What else can I check or configure? * The logging on this is minimal
    > > at best. *Not much help in troubleshooting where it's not working!!
    >

    > > Thank you,
    >

    > > Oskar
    >

    > > ps. *My goal is to allow older network equipment (copiers/scanners and
    > > some desktop software) to send email out from port 25. *We are on an
    > > ATT circuit and they have closed port 25 completely. *The idea is
    > > internally the smtp service accepts smtp connections via port 25 but
    > > then relays it via google gmail to the outside world via port 465 with
    > > encryption!

      My System SpecsSystem Spec

  4. #4


    neo Guest

    Re: advise on smtp service (windows 2003 SP2)

    Not sure... before I setup a test box, can you review the following to see
    how spot on you are with this configuration? Reason I ask is that this is
    where I would start based on the this thread.

    http://fmuntean.wordpress.com/2008/1...gmail-account/

    <pheonix1t@newsgroup> wrote in message
    news:ad0366e9-27db-4701-ad6c-dde5064f6699@newsgroup
    Yes, I did that too.
    The logging is primitive on this but I did see on the event logs
    (system) that it connects to me.com but that server won't accept the
    connection. What I'm wondering about is plenty of email servers (in
    public internet) now run strict RFC adherence. I can only wonder what
    this server looks like for valid host name, reverse DNS, valid helo
    greeting, etc.

    Maybe it's failing one or more RFC checks? Windows servers aren't
    famous for adhering to RFC rules but lots of Linux mail servers are
    VERY strict about RFC rules. I've seen lots of companies that use
    gateway SMTP servers (usually linux machines) for email to run spam/
    virus filtering. Internally they have exchange/lotus/groupwise.
    Lately you can outsource this service to google or similar (Postini).

    Thanks,

    Oskar


    On Apr 28, 6:38 am, "neo" <n...@newsgroup> wrote:

    > Not only do you have to worry about the port and SSL/TLS, but did you
    > configure outbound security to supply your g-mail credentials?
    >
    > <pheoni...@newsgroup> wrote in message
    >
    > news:d569c12c-5ea8-4b9c-8fc5-ad531c23003a@newsgroup
    >

    > > hello,
    > > I'm trying to get smtp service on 2003 server to let me relay from
    > > port 25 to gmail (smtp port 465 via SSL or TLS).
    > > I've configured the settings to outgoing = smtp.gmail.com, smtp port
    > > is set to 465 and TLS is selected.
    > > It accepts emails but they get stuck in the queue folder. The don't
    > > leave.
    >

    > > What else can I check or configure? The logging on this is minimal
    > > at best. Not much help in troubleshooting where it's not working!!
    >

    > > Thank you,
    >

    > > Oskar
    >

    > > ps. My goal is to allow older network equipment (copiers/scanners and
    > > some desktop software) to send email out from port 25. We are on an
    > > ATT circuit and they have closed port 25 completely. The idea is
    > > internally the smtp service accepts smtp connections via port 25 but
    > > then relays it via google gmail to the outside world via port 465 with
    > > encryption!

      My System SpecsSystem Spec

advise on smtp service (windows 2003 SP2)

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