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smtp server sending issues


smtp server sending issues shelly campbell
7/20/2004 10:05:11 AM
iis smtp nntp: In the last week (since Jul 14), I've been having=20
problems sending email from our web servers running IIS 5=20
and the SMTP service. I applied the latest security=20
updates: 839645, 841872, 841873, 840315, 842526 and=20
823353. Strange I'm able to telnet but no consistent=20
smtp. I've also been getting the following errors in the=20
event log trying to send to a domain that I know exists.

Please let me know if you have any ideas as to the cause.

Thanks!


Event Type: Warning
Event Source: smtpsvc
Event Category: None
Event ID: 4001
Date: 7/20/2004
Time: 10:38:13 AM
User: N/A
Computer: AGWEB1
Description:
Message delivery to the remote domain 'pop.ag-is.com'=20
failed. The error message is 'An SMTP protocol error=20
occurred.
'. The SMTP verb which caused the error is 'RCPT'. The=20
response from the remote server is '550 5.7.1 Unable to=20
relay for webmaster@pop.ag-is.com
'.=20
Data:
0000: d7 02 04 c0 =D7..=C0 =20

Event Type: Warning
Event Source: smtpsvc
Event Category: None
Event ID: 4000
Date: 7/20/2004
Time: 10:46:55 AM
User: N/A
Computer: AGWEB1
Description:
Message delivery to the remote domain 'webarkitechs.com'=20
failed for the following reason: Destination server does=20
not exist.
=20
Data:
0000: d6 02 04 c0 =D6..=C0 =20
Re: smtp server sending issues shelly
7/20/2004 1:58:29 PM
Thanks Jeff but the main issue is that I can't seem to=20
send emails from our IIS web servers to our IMail server.=20
I can telnet to it but can't send scripted emails.

IMail - 63.71.210.99
web servers - 63.71.210.6, 63.71.210.5, 63.71.210.8

I've got the smart host set to 63.71.210.99 but it's=20
still not working. Getting Status: 5.0.0 messages now.

Shelly

[quoted text, click to view]
Re: smtp server sending issues shelly
7/20/2004 7:59:31 PM
When I send a test message from the web server on=20
63.71.210.6, it sends to the IMail server ok=20
(63.71.210.99). The second test message tries to connect=20
to our internal Exchange server (10.10.10.225). Something=20
does not appear to be configured properly in DNS between=20
our internal exchange server and our servers on the DMZ.=20
We have a PIX 515 firewall that is configured for the DMZ=20
and internal servers. I'm sure that is fine.

I have DNS running on the IMail server to allow mail to=20
pass from the DMZ to our internal Exchange server (for=20
testing and sending mail to and from clients on the IMail=20
server).

Do you have any suggestions?

Thanks!



[quoted text, click to view]
Re: smtp server sending issues shelly
7/20/2004 8:00:35 PM
Forgot to send the section of the log file from the web=20
server that is sending messages to the IMail server.

sends first message from website ok (connects to IMail=20
server on DMZ)

2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
220+pop.ag-is.com+(IMail+7.15+291-4)+NT-ESMTP+Server+X1 0=20
0 55 0 0 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 EHLO -=20
agweb1.ag-is.com 0 0 4 0 0 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - - 250-
pop.ag-is.com+says+hello 0 0 28 0 0 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 MAIL -=20
FROM:<emergency@ag-is.com> 0 0 4 0 0 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
250+ok 0 0 6 0 16 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 RCPT -=20
TO:<shelly@webarkitechs.com> 0 0 4 0 16 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
250+ok+its+for+<shelly@webarkitechs.com> 0 0 40 0 31=20
SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 DATA - - 0=20
0 4 0 47 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
354+ok,+send+it;+end+with+<CRLF>.<CRLF> 0 0 39 0 47 SMTP -
- - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
250+Message+queued 0 0 18 0 47 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 QUIT - - 0=20
0 4 0 63 SMTP - - - -
2004-07-21 02:25:53 63.71.210.99=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
221+Goodbye 0 0 11 0 63 SMTP - - - -

next message sent from website tries to connect to=20
remote.ag-is.com (our internal Exchange server)

2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
220+remote.ag-
is.com+Microsoft+ESMTP+MAIL+Service,+Version:+6.0.3790.0+r
eady+at++Tue,+20+Jul+2004+22:26:44+-0400+ 0 0 113 0 0=20
SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 EHLO -=20
agweb1.ag-is.com 0 0 4 0 0 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - - 250-
remote.ag-is.com+Hello+[63.71.210.6] 0 0 40 0 0 SMTP - - -
-
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 MAIL -=20
FROM:<> 0 0 4 0 0 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
250+2.1.0+<>....Sender+OK 0 0 25 0 15 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 RCPT -=20
TO:<emergency@ag-is.com> 0 0 4 0 15 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
550+5.1.1+User+unknown 0 0 22 0 15 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 RSET - - 0=20
0 4 0 15 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
250+2.0.0+Resetting 0 0 19 0 15 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionCommand SMTPSVC1 AGWEB1 - 25 QUIT - - 0=20
0 4 0 31 SMTP - - - -
2004-07-21 02:26:44 10.10.10.225=20
OutboundConnectionResponse SMTPSVC1 AGWEB1 - 25 - -=20
221+2.0.0+remote.ag-
is.com+Service+closing+transmission+channel 0 0 63 0 31=20
SMTP - - - -
=20
=20
=20


[quoted text, click to view]
Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/20/2004 8:10:14 PM
On Tue, 20 Jul 2004 10:05:11 -0700, "shelly campbell"
[quoted text, click to view]

This was an attempted relay through the server responding to the SMTP
connection to the destination. If you're using a smart host, then you
likely do not have permission to use it. If not, the other end may
have troubles.

[quoted text, click to view]

I'm not sure why anyone gets confused by this. The destination domain
doesn't have a mail server answering. If the destination server
doesn't exist, you can't send mail to it. If your vacation
destination doesn't exist, you can't buy an airline ticket to it
either. :)

Note that the destination doesn't exist *to your mail server at the
time the connection attempt is made*. Network troubles, DNS errors,
destination system offline for a while, all could result in this.

By the way, the domain exists as I write this response.

Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/21/2004 1:36:07 AM
On Tue, 20 Jul 2004 13:58:29 -0700, "shelly"
[quoted text, click to view]

Is iMail set to allow relay from the web server IP addresses? Is
there a firewall in between? And have you checked the SMTP logs on
both the IIS server and the iMail server?

Jeff


[quoted text, click to view]
Re: smtp server sending issues shelly
7/21/2004 9:10:29 AM
We host websites here and hosted email (IMail) for=20
hosting clients (DMZ). Our Exchange Server (residing on=20
SBS 2003) is for our internal email (internal).

Some of the websites hosted here need to send email from=20
IIS/SMTP to log accounts on the IMail server. We also=20
test sending messages from websites to our own internal=20
Exchange server.

There may be a better way to do this but I don't have=20
much experience in this area.

[quoted text, click to view]
Re: smtp server sending issues shelly
7/21/2004 11:37:33 AM
Jeff,

Just what I suspected, it was a DNS issue. ;-) I just=20
resolved it. Phew!

Thanks,
Shelly

[quoted text, click to view]
Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/21/2004 3:41:37 PM
On Tue, 20 Jul 2004 19:59:31 -0700, "shelly"
[quoted text, click to view]

Sounds like iMail accepts mail from your web server but won't relay
mail from it. That's an iMail issue, and Ipswitch's knowledge base
should have answers or post on the iMail mailing list for support.

You're running three mail servers, IIS/SMTP, iMail and Exchange. Is
there a valid reason for this? Perhaps you can simplify this by
rethinking your setup.

Jeff

[quoted text, click to view]
Re: smtp server sending issues shelly
7/21/2004 8:07:47 PM
A lot of the hosting clients are using CDONTS for email=20
so we need to use SMTP running on the web server. Thanks=20
for the info per using CDO and mail components by sending=20
through the IMail server from the websites. I didn't know=20
you could do that.

Actually IMail is not allowing relays. It is configured=20
to send to the internal Exchange server in the "remote=20
mail gateway host" setting.

The mail servers on the DMZ are allowed to talk to the=20
internal Exchange server in the PIX configuration.

[quoted text, click to view]
Re: smtp server sending issues shelly
7/21/2004 8:20:50 PM
Believe it or not, our primary DNS couldn't resolve the
MX records for the domains hosted on the IMail server. I
made sure all the MX records are now pointed to the IMail
server for those domains.

I also have DNS setup on the IMail server to only resolve
our company domains (used for our internal email) to the
internal Exchange server (to send email from the DMZ to
the internal Exchange server) and to the web servers on
the DMZ. I had to add an A record for the IMail server
(DUH!). All the other web servers had a corresponding A
record.

all hosted domains on one DNS server
company domains on the IMail server
DNS running on the internal SBS 2003/Exchange server

PIX is configured for the SMTP servers on the DMZ to talk
to the internal Exchange server.

Not sure if this is the best setup but at least
everything is working now and it's been quite a learning
experience! I took over the web hosting duties last
spring and since that time I've been having to correct
DNS issues that were not setup correctly by the last
technician(s). Amazing that anything was working!

Also our internal development server can now email
outside domains, our internal Exchange server and the
IMail server on the DMZ.


[quoted text, click to view]
Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/21/2004 8:57:55 PM
On Wed, 21 Jul 2004 09:10:29 -0700, "shelly"
[quoted text, click to view]

If you're using CDO or providing a component for mail, they can send
from the website to the iMail server using iMail as the SMTP. CDONTS
needs SMTP running on the web server.

If your internal Exchange server cannot be reached directly from the
internet/DMZ then you have to relay through the iMail and iMail has to
be configured to allow the relay.

Jeff

[quoted text, click to view]
Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/21/2004 9:00:55 PM
On Wed, 21 Jul 2004 11:37:33 -0700, "shelly"
[quoted text, click to view]

DNS as in the IIS server couldn't correctly resolve the MX record for
the Exchange server? Was it an internal MX record unreachable by the
IIS system or an external DNS with an incorrect setting? Just
curious, this kind of issue pops up in the SMTP groups fairly
regularly, and it seems that firewall rules for internal/external DNS
and DNS forwarding bugger up a number of systems.

Re: smtp server sending issues shelly
7/22/2004 5:23:15 PM
Jeff,

Thanks for all of your help!

Shelly

[quoted text, click to view]
Re: smtp server sending issues jeff.nospam NO[at]SPAM zina.com
7/22/2004 7:32:32 PM
On Wed, 21 Jul 2004 20:20:50 -0700, "shelly"
[quoted text, click to view]

I believe it, that seems to be a common issue with a lot of SMTP
problems, you just happened to have control over the whole group.

[quoted text, click to view]

The other common problem is an iMail server with a system name
different from the FQDN. iMail thinks that since you named the server
"server1" then you sure wouldn't want to use a mail host name of
mail.domain .com. Unless you add the names iMail does some goofy
things sometimes.

[quoted text, click to view]

That seems like a decent arrangement, and fairly secure against relays
too. DNS always seems to be an issue with mail, you can be sloppy on
a network and if DNS is broken then Broadcasts will resolve a name.
SMTP don't play that game.

[quoted text, click to view]

Sounds like you're all set then. On to the next problem. :)

Jeff

[quoted text, click to view]
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