Troubleshooting IIS SMTP

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Message stuck in Microsoft SMTP service Queue « Axelilly’s Ponderings

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SMTPDiag - troubleshooting email issues

Steve Schofield Weblog — Sun, 13 May 2007 20:03:08 GMT

SMTPDiag is a handy tool for tracking down SMTP based issues. I recently used in a newsgroup posting

re: Troubleshooting IIS SMTP

Norm — Fri, 20 Jan 2006 14:26:25 GMT

Hey thanks again. I'll try and find some Frontpage Newsgroups and see what they say.

All I'm really trying to do is to get my website to email messages that come from a FrontPage Extentions Form on a webpage.

re: Troubleshooting IIS SMTP

qbernard — Fri, 20 Jan 2006 08:25:58 GMT

Err. I think you are having another problem. It looks like you are confuse with SMTP and not SMTP is not sending mail.
a) first of all, your Frontpage question. To be frank - I'm not sure, coz I never use frontpage before :( anyway - try post it to frontpage newsgroup.

b) IIS SMTP is design to help you relay emails. I don't configure any remote or alias for new virtual server as the default one is enough to fulfill my needs.

So, first, you need to understand what you want to do? to relay email? forward to smart host? or ?

Here's some generic SMTP KB that should give you a better picture.
HOW TO: Configure the SMTP Virtual Server for Message Delivery
http://support.microsoft.com/?id=303734

HOW TO: Configure a Remote Domain for an Internet Information Services SMTP Mail Relay Server in Windows Server 2003
http://support.microsoft.com/?id324272

HOW TO: Set SMTP Security Options in Windows Server 2003
http://support.microsoft.com/?id=324285

re: Troubleshooting IIS SMTP

Norm — Thu, 19 Jan 2006 21:30:26 GMT

HI,
I have a few questions.
I have Windows 2K with IIS with Frontpage Extentions running. I want to be able to setup Forms in Frontpage so that when the form is filled out, it will be sent to an email address. Right now when I try this, I get an Event Log saying "unknown email address".
I guess my question is in IIS, is the Virtual SMTP Server the only thing that has to be setup to get this to work?

I found some information on how to setup the Virtual SMTP Server but it is still confusing. For example, in IIS under the SMTO Virtual Server under Domain, select NEW - DOMAIN then I have a choose between Remote or Alias, I think this should be Remote so I choose Remote. Then it asks "What is the address space of mail that is to be delivered by this domain? Do I just make up a name and put it in the box??? I did try that but I get the error mentioned above.

Thanks for any help.

re: Troubleshooting IIS SMTP

qbernard — Sat, 14 Jan 2006 12:38:23 GMT

Hi Prady,
Obviously from the event log and smtpdiag log. it is indicating that your host is unable to connect to the remote smtp server on port 25. Make sure this port is not blocked by your firewall, etc.

re: Troubleshooting IIS SMTP

Prady — Thu, 12 Jan 2006 08:40:58 GMT

Hi,

I am unable to send emails to yahoo/gmail or hotmail a/c . I am using win2003 server with iis 6. I am able to send mails within the organization but not able to send it to other accounts.I get a delivery failure . The event log log returns this message

=========================================

Message delivery to the host '66.249.83.114' failed while delivering to the remote domain 'gmail.com' for the following reason: The remote server did not respond to a connection attempt.

==========================================

Any pointers on what could be the reason.

The reports after running the smtpdiag are these..

Searching for Exchange external DNS settings.
Computer name is E2ESCV2.
Failed to bind to search. Error: 8007054b

Checking SOA for gmail.com.
Checking external DNS servers.
Checking internal DNS servers.

Checking TCP/UDP SOA serial number using DNS server [16.138.16.52].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005122000

Checking TCP/UDP SOA serial number using DNS server [16.138.16.104].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005122000
SOA serial number match: Passed.

Checking local domain records.
Starting TCP and UDP DNS queries for the local domain. This test will try to
validate that DNS is set up correctly for inbound mail. This test can fail for
3 reasons.
1) Local domain is not set up in DNS. Inbound mail cannot be routed to
local mailboxes.
2) Firewall blocks TCP/UDP DNS queries. This will not affect inbound mail,
but will affect outbound mail.
3) Internal DNS is unaware of external DNS settings. This is a valid
configuration for certain topologies.
Checking MX records using TCP: xx.com.
MX: smtp.xx.com (10)
MX: smtpx.xx.com (30)
A: smtp.xx.com [192.151.81.254]
A: smtpx.xx.com [15.81.168.21]
A: smtpx.xx.com [15.81.176.20]
A: smtpx.xx.com [15.81.176.21]
A: smtpx.xx.com [15.45.89.154]
A: smtpx.xx.com [15.45.89.155]
A: smtpx.xx.com [15.45.89.156]
A: smtpx.xx.com [15.45.89.157]
A: smtpx.xx.com [15.81.168.20]
Checking MX records using UDP: xx.com.
MX: smtp.xx.com (10)
MX: smtpx.xx.com (30)
A: smtp.xx.com [192.151.81.254]
A: smtpx.xx.com [15.81.176.20]
A: smtpx.xx.com [15.81.176.21]
A: smtpx.xx.com [15.45.89.154]
A: smtpx.xx.com [15.45.89.155]
A: smtpx.xx.com [15.45.89.156]
A: smtpx.xx.com [15.45.89.157]
A: smtpx.xx.com [15.81.168.20]
A: smtpx.xx.com [15.81.168.21]
Both TCP and UDP queries succeeded. Local DNS test passed.

Checking remote domain records.
Starting TCP and UDP DNS queries for the remote domain. This test will try to
validate that DNS is set up correctly for outbound mail. This test can fail for
3 reasons.
1) Firewall blocks TCP/UDP queries which will block outbound mail. Windows
2000/NT Server requires TCP DNS queries. Windows Server 2003 will use UDP
queries first, then fall back to TCP queries.
2) Internal DNS does not know how to query external domains. You must
either use an external DNS server or configure DNS server to query external
domains.
3) Remote domain does not exist. Failure is expected.
Checking MX records using TCP: gmail.com.
MX: gmail-smtp-in.l.google.com (5)
MX: gsmtp83.google.com (10)
MX: gsmtp163.google.com (10)
MX: gsmtp185.google.com (10)
MX: gsmtp83-2.google.com (10)
MX: gsmtp185-2.google.com (10)
A: gsmtp83.google.com [66.249.83.27]
A: gsmtp163.google.com [64.233.163.27]
A: gsmtp185.google.com [64.233.185.27]
A: gsmtp83-2.google.com [66.249.83.114]
Checking MX records using UDP: gmail.com.
MX: gmail-smtp-in.l.google.com (5)
MX: gsmtp83.google.com (10)
MX: gsmtp163.google.com (10)
MX: gsmtp185.google.com (10)
MX: gsmtp83-2.google.com (10)
MX: gsmtp185-2.google.com (10)
Both TCP and UDP queries succeeded. Remote DNS test passed.
A: gmail-smtp-in.l.google.com [64.233.163.27]
A: gmail-smtp-in.l.google.com [64.233.163.114]
A: gsmtp185-2.google.com [64.233.185.114]

Checking MX servers listed for pradykris@gmail.com.
Connecting to gmail-smtp-in.l.google.com [64.233.163.114] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gmail-smtp-in.l.google.com.
Connecting to gmail-smtp-in.l.google.com [64.233.163.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gmail-smtp-in.l.google.com.
Connecting to gsmtp185-2.google.com [64.233.185.114] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gsmtp185-2.google.com.
Connecting to gsmtp83-2.google.com [66.249.83.114] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gsmtp83-2.google.com.
Connecting to gsmtp185.google.com [64.233.185.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gsmtp185.google.com.
Connecting to gsmtp163.google.com [64.233.163.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gsmtp163.google.com.
Connecting to gsmtp83.google.com [66.249.83.27] on port 25.
Connecting to the server failed. Error: 10061
Failed to submit mail to gsmtp83.google.com.

Question: SMTP not sending mail

TrackBack — Fri, 07 Oct 2005 18:59:00 GMT

Question: SMTP not sending mail

TrackBack — Fri, 07 Oct 2005 18:48:00 GMT

re: Troubleshooting IIS SMTP

bernard — Wed, 17 Aug 2005 14:55:00 GMT

From the log, it shows that your smtp is working correctly. Are you experiencing the mail get sent but not received at the other end? e.g. emails not delivered to hotmail/yahoo mailbox. The possible reason that your mail hosts is blacklisted, or doesn't pass their filter rules (e.g. has a valid reverse lookup name), etc.

re: Troubleshooting IIS SMTP

bernard — Tue, 16 Aug 2005 10:34:00 GMT

I'm also having touble sending email form a windows 2003 server. I downloaded SMTPDiag and below afre the results, Unfortunatly I'm much more of a developer than a network guy, do you have any ideas what the problem might be? Thanks for you help.

Searching for Exchange external DNS settings.
Computer name is NS1.
Failed to connect to the domain controller. Error: 8007054b

Checking SOA for yahoo.com.
Checking external DNS servers.
Checking internal DNS servers.

Checking TCP/UDP SOA serial number using DNS server [70.84.160.11].
TCP test failed.
UDP test succeeded.
Serial number: 2005081508

Checking TCP/UDP SOA serial number using DNS server [70.84.161.11].
TCP test failed.
UDP test succeeded.
Serial number: 2005081508
SOA serial number match: Passed.

Checking local domain records.
Starting TCP and UDP DNS queries for the local domain. This test will try to
validate that DNS is set up correctly for inbound mail. This test can fail for
3 reasons.
1) Local domain is not set up in DNS. Inbound mail cannot be routed to
local mailboxes.
2) Firewall blocks TCP/UDP DNS queries. This will not affect inbound mail,
but will affect outbound mail.
3) Internal DNS is unaware of external DNS settings. This is a valid
configuration for certain topologies.
Checking MX records using TCP: hubshift.com.
Warning: The TCP DNS query returned no results.
Checking MX records using UDP: hubshift.com.
MX: mailstore1.secureserver.net (10)
MX: smtp.secureserver.net (0)
A: smtp.secureserver.net [64.202.166.12]
A: mailstore1.secureserver.net [64.202.166.11]
A: PARK5.secureserver.net [64.202.165.110]
A: PARK6.secureserver.net [64.202.167.149]

Checking remote domain records.
Starting TCP and UDP DNS queries for the remote domain. This test will try to
validate that DNS is set up correctly for outbound mail. This test can fail for
3 reasons.
1) Firewall blocks TCP/UDP queries which will block outbound mail. Windows
2000/NT Server requires TCP DNS queries. Windows Server 2003 will use UDP
queries first, then fall back to TCP queries.
2) Internal DNS does not know how to query external domains. You must
either use an external DNS server or configure DNS server to query external
domains.
3) Remote domain does not exist. Failure is expected.
Checking MX records using TCP: yahoo.com.
Warning: The TCP DNS query returned no results.
Checking MX records using UDP: yahoo.com.
MX: mx3.mail.yahoo.com (1)
MX: mx4.mail.yahoo.com (5)
MX: mx1.mail.yahoo.com (1)
MX: mx2.mail.yahoo.com (1)
A: mx1.mail.yahoo.com [67.28.113.10]
A: mx1.mail.yahoo.com [67.28.113.11]
A: mx1.mail.yahoo.com [4.79.181.14]
A: mx1.mail.yahoo.com [4.79.181.15]
A: mx2.mail.yahoo.com [67.28.114.35]
A: mx2.mail.yahoo.com [67.28.114.36]
A: mx2.mail.yahoo.com [4.79.181.13]
A: mx2.mail.yahoo.com [64.156.215.8]
A: mx3.mail.yahoo.com [4.79.181.12]
A: mx3.mail.yahoo.com [64.156.215.5]
A: mx3.mail.yahoo.com [64.156.215.6]
A: mx3.mail.yahoo.com [64.156.215.18]
A: mx4.mail.yahoo.com [67.28.113.19]
A: mx4.mail.yahoo.com [68.142.202.11]
A: mx4.mail.yahoo.com [68.142.202.12]
A: mx4.mail.yahoo.com [66.218.86.156]

Checking MX servers listed for kywillis@yahoo.com.
Connecting to mx3.mail.yahoo.com [64.156.215.18] on port 25.
Received:
220 mta340.mail.scd.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta340.mail.scd.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta340.mail.scd.yahoo.com

Successfully connected to mx3.mail.yahoo.com.
Connecting to mx3.mail.yahoo.com [64.156.215.6] on port 25.
Received:
220 mta189.mail.scd.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta189.mail.scd.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta189.mail.scd.yahoo.com

Successfully connected to mx3.mail.yahoo.com.
Connecting to mx3.mail.yahoo.com [64.156.215.5] on port 25.
Received:
220 mta151.mail.scd.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta151.mail.scd.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta151.mail.scd.yahoo.com

Successfully connected to mx3.mail.yahoo.com.
Connecting to mx2.mail.yahoo.com [64.156.215.8] on port 25.
Received:
220 mta311.mail.scd.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta311.mail.scd.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta311.mail.scd.yahoo.com

Successfully connected to mx2.mail.yahoo.com.
Connecting to mx2.mail.yahoo.com [4.79.181.13] on port 25.
Received:
220 mta153.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta153.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta153.mail.mud.yahoo.com

Successfully connected to mx2.mail.yahoo.com.
Connecting to mx2.mail.yahoo.com [67.28.114.36] on port 25.
Received:
220 mta202.mail.dcn.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta202.mail.dcn.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta202.mail.dcn.yahoo.com

Successfully connected to mx2.mail.yahoo.com.
Connecting to mx1.mail.yahoo.com [4.79.181.15] on port 25.
Received:
220 mta242.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta242.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta242.mail.mud.yahoo.com

Successfully connected to mx1.mail.yahoo.com.
Connecting to mx1.mail.yahoo.com [4.79.181.14] on port 25.
Received:
220 mta219.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta219.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta219.mail.mud.yahoo.com

Successfully connected to mx1.mail.yahoo.com.
Connecting to mx1.mail.yahoo.com [67.28.113.11] on port 25.
Received:
220 mta183.mail.re2.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta183.mail.re2.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta183.mail.re2.yahoo.com

Successfully connected to mx1.mail.yahoo.com.
Connecting to mx2.mail.yahoo.com [67.28.114.35] on port 25.
Received:
220 mta140.mail.dcn.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta140.mail.dcn.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta140.mail.dcn.yahoo.com

Successfully connected to mx2.mail.yahoo.com.
Connecting to mx1.mail.yahoo.com [67.28.113.10] on port 25.
Received:
220 mta135.mail.re2.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta135.mail.re2.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta135.mail.re2.yahoo.com

Successfully connected to mx1.mail.yahoo.com.
Connecting to mx3.mail.yahoo.com [4.79.181.12] on port 25.
Received:
220 mta113.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta113.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta113.mail.mud.yahoo.com

Successfully connected to mx3.mail.yahoo.com.
Connecting to mx4.mail.yahoo.com [66.218.86.156] on port 25.
Received:
220 mta263.mail.scd.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta263.mail.scd.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta263.mail.scd.yahoo.com

Successfully connected to mx4.mail.yahoo.com.
Connecting to mx4.mail.yahoo.com [68.142.202.12] on port 25.
Received:
220 mta230.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta230.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta230.mail.mud.yahoo.com

Successfully connected to mx4.mail.yahoo.com.
Connecting to mx4.mail.yahoo.com [68.142.202.11] on port 25.
Received:
220 mta217.mail.mud.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta217.mail.mud.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta217.mail.mud.yahoo.com

Successfully connected to mx4.mail.yahoo.com.
Connecting to mx4.mail.yahoo.com [67.28.113.19] on port 25.
Received:
220 mta213.mail.re2.yahoo.com ESMTP YSmtp service ready

Sent:
ehlo hubshift.com

Received:
250-mta213.mail.re2.yahoo.com
250-8BITMIME
250-SIZE 31981568
250 PIPELINING

Sent:
mail from: <kywillis@hubshift.com>

Received:
250 sender <kywillis@hubshift.com> ok

Sent:
rcpt to: <kywillis@yahoo.com>

Received:
250 recipient <kywillis@yahoo.com> ok

Sent:
quit

Received:
221 mta213.mail.re2.yahoo.com

Successfully connected to mx4.mail.yahoo.com.

re: Troubleshooting IIS SMTP

bernard — Fri, 12 Aug 2005 19:51:00 GMT

Can you post the complete smtpdiag log? I'm guessing the remote mail server rejected the mail. pls look at the smtp log files. It could be your mail host is not a valid host (e.g. complete with reverse lookup dns record), not in whitelist or it's blacklisted, etc.

And it's not really smtp issue as you can send to certain domains, but rather the smtp host itself been able to send mail like the rest of those valid mail server.

re: Troubleshooting IIS SMTP

bernard — Fri, 12 Aug 2005 10:27:00 GMT

I am having trouble with my email. I am able to send email to some accounts and others it fails. I ran the SMPTdiagtool and get the following.

error expected 250 smtp.pp.htv.fi

I'm not sure what is happening. I also notice that emails to AOL fail.

Thanks

HW

re: Troubleshooting IIS SMTP

bernard — Sat, 30 Jul 2005 15:55:00 GMT

Can you run smtpdiag when the problem occurs? use verbose mode and post the output here.

re: Troubleshooting IIS SMTP

bernard — Sat, 30 Jul 2005 01:28:00 GMT

Having 'internal dns error' for the past 6 months. After running fine for few hours, my dedicated server will fail.

Upon failure. I get the following results:
- ping an external IP fails
- ping an external domain (ip show up) fails
- ping internal domain OK
- nslookup for internal and external domains OK
- Browser fails on both internal and external website.
- Email client can access mails
- Email client can send mails but mails will get stuck in queue for resend.
- Web cdo mail fails, goes to queue for resend.

After rebooting the server, all mail queue will goes out. All the abovemention problems do not exist until several hours later.

Any suggestions would be greatly appreciated.

Larry
http://www.geromail.com

re: Troubleshooting IIS SMTP

bernard — Mon, 09 May 2005 15:46:00 GMT

Hi Joe,

What kind of mail volume we are looking here? 10K per day? did you actually found any 'mails' stuck in badmail/drop under the mailroot/ folder? Lastly, any errors in smtp log?

I have seen this behavior before in one of my previous setup. Roughly 40K mails a day, hence the log is huge and you never know whether the mail really get delivered or not, it just too many. This could be due to heavy traffic and at that particular time. Under default setup, smtp will try to resend the mail. What you need to do one is to check if user complaint about mail not being delivered, then check the mail folder and smtp log to see if there's more clues to troubleshoot.

Cheers.

re: Troubleshooting IIS SMTP

bernard — Fri, 06 May 2005 06:49:00 GMT

We run MS Exchange 5.5 on an NT 4.0 box.
Our mx record points to our public IP address.
Our firewall then forwards SMTP email to our Exchange 5.5
We have been successfully sending/receiving internet email for years and do not have an open relay.

Let's call my internet email domain address abcdnet.com. This as well as mail.abcdnet.com point to our public IP address.

Last week I setup a Windows 2000 IIS server to act as a SMTP relay for inbound mail only. I got it to work and it worked fairly well until yesterday. I started to receive event log messages stating:
"Message delivery to remote domain 'abcdnet.com' failed ...: The connection was dropped by the remote host'.

I'm not sure why after 5 days of working this started to happen. How would I trouble shoot this? Here is what I did when I installed the SMTP relay.

1) Edited Exchange Server's file c:\winnt\system32\driver\etc\services to default SMTP to port 26 (previously 25).

2) On the IIS box Default SMTP Server Properties->General->Connection I changed the Outgoing TCP port to 26

3) On the IIS box UNDER the Default SMTP Server I created a remote domain named called "abcdnet.com". Under properties I have checked 'Allow incoming mail to be relayed through this domain' checked. I also 'Forward all mail to smart host': internal IP address of Exchange Server.

4) I then pointed the smtp port in the firewall to point to the IIS box.

This setup was partially due to Symantec's suggestions for setting up a relay to be used with their anti-spam server, which is currently not setup.

So I am wondering if perhaps I did something wrong. It worked for 4 days then stopped. We did get hit by a lot of virus emails yesterday (sobe?) so we did have a higher than normal load, yet nothing seems to have become infected. It as if the SMTP relay got bogged down somehow. Everythign was working fine then just not.

re: Troubleshooting IIS SMTP

bernard — Wed, 23 Mar 2005 16:41:00 GMT

This could happen when the remote server blacklist you or etc. I have a smtp test server that can only send to yahoo mailbox, but not gmail or hotmail, because both gmail and hotmail doesn't recognize the smtp box, etc. hence though it got deliever, but it doesn't reach the mail box.

re: Troubleshooting IIS SMTP

bernard — Wed, 23 Mar 2005 15:16:00 GMT

Hey listen, thank you for taking the time to look at my problem. I saw no errors in the log and i didn't see any emails in yahoo , hotmail or gmail. I did a port scan and all necessary ports r ok. Anyhow, thanks for ur help, i just used no-ip and forwarded email to there and it went through fine. Weird.