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advise on smtp service (windows 2003 SP2)

P

pheonix1t

#1
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 Computer

#2
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 Computer

P

pheonix1t

#3
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 Computer

#4
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/...rver-to-forward-emails-using-a-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 Computer

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