Smart Host is not sending any authentication information.

This seems like this should be easy but it is not working for me at all.

I have configured on my Windows/2000 Professional the SMTP services.

The intent is that outbound messages should go to my ISP for processing. So
I added under the "Delivery" tab - under "Advanced" my Smart Host's IP
address with the brackets "[]" and have cleared the "Attempt Direct Delivery
before sending to Smart Host.

Under the "Outbound Security" I selected "Basic authentication" and put in
my user name and password for the ISP server.

So what happens is my little SMTP server does indeed take the messages,
makes a connnection to the "Smart Host". But does not send the
authentication information.

A short look at the SMTP event log shows the handshake but no indication of
the userid or passwoard being sent. What happened? Is there some
configuration point I am missing here?

Thanks in advance for the help!

Here is the redacted log file...

25 EHLO - bernie 0 0 4 0 2243 SMTP - - - -
25 - - 250-smtp816.mail.sc5.yahoo.com 0 0 30 0 2313 SMTP - - - -
25 MAIL - FROM:<Bernard_Luksich@CompuServe.Com
25 - -
530+authentication+required+-for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 25 QUIT - - 0 0 4 0 2453 SMTP - - - -
25 - - 220+smtp806.mail.sc5.yahoo.com+ESMTP 0 0 36 0 691 SMTP - - - -
25 EHLO - bernie 0 0 4 0 691 SMTP - - - -
25 - - 250-smtp806.mail.sc5.yahoo.com 0 0 30 0 772 SMTP - - - -
25 MAIL - FROM:<> 0 0 4 0 782 SMTP - - - -
25 - -
530+authentication+required+-+for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 103 0 882 SMTP - - - -
25 QUIT - - 0 0 4 0 912 SMTP - - -

Nick>
Thu Jun 16 17:29:20 CDT 2005

I had the exact same problem, I spent ages on it but could not find a
solution or get it working. Instead I had to allow replay from this IP
address at the SMTP server.

--
:: nick dell
:: programming & hosting
:: www.blnk.co.uk
"Bernie" <Bernie@discussions.microsoft.com> wrote in message
news:74E3FBD5-5A89-4E2C-AFA3-935543366329@microsoft.com...
> This seems like this should be easy but it is not working for me at all.
>
> I have configured on my Windows/2000 Professional the SMTP services.
>
> The intent is that outbound messages should go to my ISP for processing.
So
> I added under the "Delivery" tab - under "Advanced" my Smart Host's IP
> address with the brackets "[]" and have cleared the "Attempt Direct
Delivery
> before sending to Smart Host.
>
> Under the "Outbound Security" I selected "Basic authentication" and put in
> my user name and password for the ISP server.
>
> So what happens is my little SMTP server does indeed take the messages,
> makes a connnection to the "Smart Host". But does not send the
> authentication information.
>
> A short look at the SMTP event log shows the handshake but no indication
of
> the userid or passwoard being sent. What happened? Is there some
> configuration point I am missing here?
>
> Thanks in advance for the help!
>
> Here is the redacted log file...
>
> 25 EHLO - bernie 0 0 4 0 2243 SMTP - - - -
> 25 - - 250-smtp816.mail.sc5.yahoo.com 0 0 30 0 2313 SMTP - - - -
> 25 MAIL - FROM:<Bernard_Luksich@CompuServe.Com
> 25 - -
>
530+authentication+required+-for+help+go+to+http://help.yahoo.com/help/us/sb
c/dsl/mail/pop/pop-11.html 0 0 25 QUIT - - 0 0 4 0 2453 SMTP - - - -
> 25 - - 220+smtp806.mail.sc5.yahoo.com+ESMTP 0 0 36 0 691 SMTP - - - -
> 25 EHLO - bernie 0 0 4 0 691 SMTP - - - -
> 25 - - 250-smtp806.mail.sc5.yahoo.com 0 0 30 0 772 SMTP - - - -
> 25 MAIL - FROM:<> 0 0 4 0 782 SMTP - - - -
> 25 - -
>
530+authentication+required+-+for+help+go+to+http://help.yahoo.com/help/us/s
bc/dsl/mail/pop/pop-11.html 0 0 103 0 882 SMTP - - - -
> 25 QUIT - - 0 0 4 0 912 SMTP - - -

Bernie
Thu Jun 16 21:19:01 CDT 2005

Well, thanks for the comment on this. Of course this is not what I wanted to
hear. It would then seem that this is a "bug" with the SMTP virtual server
that is part of Windows 2000/Pro.

This evening we have the virtual server on our Windows 2000 Server working
just fine with basically the same configuration.

Has anyone out there reported this as a bug to Microsoft before? From what
I see the virtual server complete ignores the "authentication" information on
outbound connects..smart host or otherwise.

Thanks again for the comment, Nick. This might save us some time of
continuing to experiment with this.

Bernie

jeff
Thu Jun 16 21:35:28 CDT 2005

On Thu, 16 Jun 2005 14:40:06 -0700, Bernie
<Bernie@discussions.microsoft.com> wrote:

>This seems like this should be easy but it is not working for me at all.
>
>I have configured on my Windows/2000 Professional the SMTP services.
>
>The intent is that outbound messages should go to my ISP for processing. So
>I added under the "Delivery" tab - under "Advanced" my Smart Host's IP
>address with the brackets "[]" and have cleared the "Attempt Direct Delivery
>before sending to Smart Host.
>
>Under the "Outbound Security" I selected "Basic authentication" and put in
>my user name and password for the ISP server.
>
>So what happens is my little SMTP server does indeed take the messages,
>makes a connnection to the "Smart Host". But does not send the
>authentication information.
>
>A short look at the SMTP event log shows the handshake but no indication of
>the userid or passwoard being sent. What happened? Is there some
>configuration point I am missing here?

Might be your ISP is where the problem lies. Have you talked to them
about it?

Jeff

>Thanks in advance for the help!
>
>Here is the redacted log file...
>
>25 EHLO - bernie 0 0 4 0 2243 SMTP - - - -
>25 - - 250-smtp816.mail.sc5.yahoo.com 0 0 30 0 2313 SMTP - - - -
>25 MAIL - FROM:<Bernard_Luksich@CompuServe.Com
>25 - -
>530+authentication+required+-for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 25 QUIT - - 0 0 4 0 2453 SMTP - - - -
>25 - - 220+smtp806.mail.sc5.yahoo.com+ESMTP 0 0 36 0 691 SMTP - - - -
>25 EHLO - bernie 0 0 4 0 691 SMTP - - - -
>25 - - 250-smtp806.mail.sc5.yahoo.com 0 0 30 0 772 SMTP - - - -
>25 MAIL - FROM:<> 0 0 4 0 782 SMTP - - - -
>25 - -
>530+authentication+required+-+for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 103 0 882 SMTP - - - -
>25 QUIT - - 0 0 4 0 912 SMTP - - -

Bernard
Fri Jun 17 01:10:22 CDT 2005

I have done this before in W2k Server IIS5. can you look at the smtp log
file and see at which point it fail ?

--
Regards,
Bernard Cheah
http://www.microsoft.com/iis/
http://www.iiswebcastseries.com/
http://www.msmvps.com/bernard/


"Bernie" <Bernie@discussions.microsoft.com> wrote in message
news:BF56F419-8EDB-4A44-94CC-055930C7EA89@microsoft.com...
> Well, thanks for the comment on this. Of course this is not what I wanted
> to
> hear. It would then seem that this is a "bug" with the SMTP virtual
> server
> that is part of Windows 2000/Pro.
>
> This evening we have the virtual server on our Windows 2000 Server working
> just fine with basically the same configuration.
>
> Has anyone out there reported this as a bug to Microsoft before? From
> what
> I see the virtual server complete ignores the "authentication" information
> on
> outbound connects..smart host or otherwise.
>
> Thanks again for the comment, Nick. This might save us some time of
> continuing to experiment with this.
>
> Bernie
>

Bernie
Fri Jun 17 09:53:10 CDT 2005

Bernard, thanks for the reply. We have the "Smart Host" running on our
Windows 2000 Server. It is the same ISP and everything works just great.
The SMTP log from the Windows 2000 Server shows the "AUTH" being done
correctly as expected.

So it was quite a shock that it was not working on our Windows 2000
Profession machine. The information is entered the same way (there aren't
quite as many selections on the protocol, for example Windows 2000 Server
allows you to select either "HELO" or "EHLO")

The section of the SMTP log is in the original message an it shows that the
initial handshake takes place. However, the IIS SMTP server immediately
tries to send an e-mail with no "AUTH" taking place. Therefore, the remote
server rejects the attempt.

Hope that helps...and thanks for he quick response.

Bernie

--
Bernie


"Bernard Cheah [MVP]" wrote:

> I have done this before in W2k Server IIS5. can you look at the smtp log
> file and see at which point it fail ?
>
> --
> Regards,
> Bernard Cheah
> http://www.microsoft.com/iis/
> http://www.iiswebcastseries.com/
> http://www.msmvps.com/bernard/

Bernie
Fri Jun 17 09:58:03 CDT 2005

Jeff, thanks for the taking the time to look into our problem...it is
appreciated.

To your question, no we have not contacted the ISP yet.

However, we are pretty sure the problem is not there. We have a
Windows/2000 Server running on the same network. The SMTP Virtual Server on
that machine is properly sending the "AUTH" to the Smart Host and mail is
flowing like water through that connect.

We have configured the SMTP Server on the Windows/2000 Professional machine.
And as noted in the SMTP log file there is no "AUTH" being sent to the Smart
Host. The configuration is the same...one works the other does not.

However, we will give them a call but given that situation I think they are
going to say "Hey..your other machine is working...your problem" and not put
much energy on the problem.

But that is an idea and we will schedule that discussion for tomorrow.

Again, Jeff, thanks the help...if you can think of something else to try let
us know.

Bernie

"Jeff Cochran" wrote:


>
> Might be your ISP is where the problem lies. Have you talked to them
> about it?
>
> Jeff
>
> >Thanks in advance for the help!
> >
> >Here is the redacted log file...
> >
> >25 EHLO - bernie 0 0 4 0 2243 SMTP - - - -
> >25 - - 250-smtp816.mail.sc5.yahoo.com 0 0 30 0 2313 SMTP - - - -
> >25 MAIL - FROM:<Bernard_Luksich@CompuServe.Com
> >25 - -
> >530+authentication+required+-for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 25 QUIT - - 0 0 4 0 2453 SMTP - - - -
> >25 - - 220+smtp806.mail.sc5.yahoo.com+ESMTP 0 0 36 0 691 SMTP - - - -
> >25 EHLO - bernie 0 0 4 0 691 SMTP - - - -
> >25 - - 250-smtp806.mail.sc5.yahoo.com 0 0 30 0 772 SMTP - - - -
> >25 MAIL - FROM:<> 0 0 4 0 782 SMTP - - - -
> >25 - -
> >530+authentication+required+-+for+help+go+to+http://help.yahoo.com/help/us/sbc/dsl/mail/pop/pop-11.html 0 0 103 0 882 SMTP - - - -
> >25 QUIT - - 0 0 4 0 912 SMTP - - -
>
>

Bernard
Sat Jun 18 23:15:49 CDT 2005

Interesting. Well, I have not really tested it with w2k pro. but was
surprise with your claimed. Can you have a simple test for both w2k and w2k
pro. Then post the two log entries here.

--
Regards,
Bernard Cheah
http://www.microsoft.com/iis/
http://www.iiswebcastseries.com/
http://www.msmvps.com/bernard/


"Bernie" <Bernie@discussions.microsoft.com> wrote in message
news:5CEE770D-880F-4BB0-B735-92837609168A@microsoft.com...
> Bernard, thanks for the reply. We have the "Smart Host" running on our
> Windows 2000 Server. It is the same ISP and everything works just great.
> The SMTP log from the Windows 2000 Server shows the "AUTH" being done
> correctly as expected.
>
> So it was quite a shock that it was not working on our Windows 2000
> Profession machine. The information is entered the same way (there aren't
> quite as many selections on the protocol, for example Windows 2000 Server
> allows you to select either "HELO" or "EHLO")
>
> The section of the SMTP log is in the original message an it shows that
> the
> initial handshake takes place. However, the IIS SMTP server immediately
> tries to send an e-mail with no "AUTH" taking place. Therefore, the
> remote
> server rejects the attempt.
>
> Hope that helps...and thanks for he quick response.
>
> Bernie
>
> --
> Bernie
>
>
> "Bernard Cheah [MVP]" wrote:
>
>> I have done this before in W2k Server IIS5. can you look at the smtp log
>> file and see at which point it fail ?
>>
>> --
>> Regards,
>> Bernard Cheah
>> http://www.microsoft.com/iis/
>> http://www.iiswebcastseries.com/
>> http://www.msmvps.com/bernard/
>

Bernie
Mon Jun 20 10:31:01 CDT 2005

Bernard, thanks again for getting back with us. I am surprised also by the
difference between the two. Attached to my first message is the logging
information from the Windows 2000 Professional vesion of the SMTP Virtual
Server.

It was actually when I looked at the log file for the Windows 2000 Server
that I noticed that logfile showed the "AUTH" being sent to the Smart Host.
I then created a quick message and logged the output of the SMTP Virtual
Server on the Windows 2000 Professional machine. And then the immediate
problem became clear...there is no password/userid information being sent and
that was explaining why no mail was leaving the system.

It will most likely be tonight when I can capture a log on the Server
machine so you can see the difference.

Thanks again for the quick response.

Bernie

Bernard
Sat Jun 25 00:00:27 CDT 2005

Ok, keep us posted. I'm traveling so response will be slow.

--
Regards,
Bernard Cheah
http://www.microsoft.com/iis/
http://www.iiswebcastseries.com/
http://www.msmvps.com/bernard/


"Bernie" <Bernie@discussions.microsoft.com> wrote in message
news:C715BB07-F846-453D-B625-0086F781ED06@microsoft.com...
> Bernard, thanks again for getting back with us. I am surprised also by
> the
> difference between the two. Attached to my first message is the logging
> information from the Windows 2000 Professional vesion of the SMTP Virtual
> Server.
>
> It was actually when I looked at the log file for the Windows 2000 Server
> that I noticed that logfile showed the "AUTH" being sent to the Smart
> Host.
> I then created a quick message and logged the output of the SMTP Virtual
> Server on the Windows 2000 Professional machine. And then the immediate
> problem became clear...there is no password/userid information being sent
> and
> that was explaining why no mail was leaving the system.
>
> It will most likely be tonight when I can capture a log on the Server
> machine so you can see the difference.
>
> Thanks again for the quick response.
>
> Bernie
>