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Problem sending smtp from one SBS to a second SBS.

I have a problem with sending messages from one SBS running Exchange Server 2003, Ill call it server B, to a second one Ill call server A.

I can send any email from server A to server B.
I can send email from server B to server A if it is just a small text message, most of the time and it may be delayed. Messages with attachments get stuck in the Queue.

I can send email to and from server B with other domains such as hotmail with out issues.
I can send email to and from other domains with server A without issues.

I administrate both servers.
I have run SMTPDIAG on both servers, testing the other with no problem detected.
I have built a bare server to replace server A as a test with no change. Due to the circumstances I can not do the same for the other server.


Any ideas will be greatly appreciated.




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aaskew
Asked:
aaskew
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1 Solution
 
SembeeCommented:
What is the connection between these two servers?
Same LAN?
VPN?
Just going over the internet like all other messages?

Are you using a smart host for email delivery?

Simon.
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aaskewAuthor Commented:
It's over the internet and no smart host is used.

Andy..
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BembiCEOCommented:
That means, both SBS servers are independend from each other, right?

As your mail flow seems to work without limitations to public target, I would say, every server works fine for it's own.
So your main problem is, that you cannot send attachements or large emails from server B to A, correct?

Questions:
1.) As you indent to move the server, are the two servers responsible for the same mail domain?
2.) Have you checked, if there are any limitations set (size, attachement types etc.) on one of the servers.
3.) Waht kind of attachement to try to send, do this happens with all kinds of attachement?
4.) Have you had a look at the mails in the queue? If you open them, there is a meesage at the end of the dialog.
5.) Have you enabled SMTP log so see, which error messages you get there (somtimes more detailed).
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aaskewAuthor Commented:
1. No, the domains are completly independent and related in no way.
2. I have opened the file size completly, no limitation.
3. It will happen with any attachement, zip, pdf, txt, etc. No filtering is on.
4. Ill take a look.
5. Ill take a look..

Thanks,
Andy.
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aaskewAuthor Commented:
For #5 above. On server B the SMTP Virt. Server is loging the following on connection attempts to server A.

504+Need+to+authenticate+first 0 0 30 0 391 SMTP - - - -

Andy..
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BembiCEOCommented:
That's it, somewhere you have set an autehntication mode. You have to allow, that either a foreign server can authenticate anonymous, or you have to exlicitely allow the IP address of the other server to make a connection to your server.

Have a look at the receiving server, if there are any different relay restrictions or security setting than on your other server. You just can compare the setting with the other server. (Properties of your virtual SMTP server)

As I cannot see, if this is an incomming or outgoing request
if server B logs outgoing, have a look at server A
if server B logs incoming, have a look at server B
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aaskewAuthor Commented:
There are no restrictions on the receiving or sending server.
No relay servers are configured on either server.

I have been able to eliminate the authenticate message by configuring the connector to send HELO instead of EHLO but the messages remain in the queue. I attempted this based on KB818222.

Andy..

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aaskewAuthor Commented:
Note: So far, the problem only affects messages with attachments.

Increasing points to 500.

Andy..
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BembiCEOCommented:
The message within the SMTP log point to the need of authentication on the target system. This is a property of your virtual SMTP server, where you can set anonymous access or other authentication methods. If anonymous acces sis disabled, you have to send an authentication to the server first, before you can do anything with this server.

Have a look at the security settings of your virtual SMTP server.

To verify this issue, you can try to send a mail to your server via telnet, you should get the same error message (as the virtual SMTP server does nothing else).

If you want to keep authentication needs, you can set an account within your virtual SMTP server, better a connector as you can limit the authentication to a single target server. There is a button, outgoing security
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aaskewAuthor Commented:
Anonymous access is anabled.

Any other server/domain can successfully send email to the server even with large attachements.
I have attempted to configure a connector specificaly for this server with the same results.

Herer is the connector log on the sending server. This is all it logs, no quit or 221 "Bye".

2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionResponse SMTPSVC1 SERVER-B - 25 - - 220+domain-a.com+Microsoft+ESMTP+MAIL+Service,+Version:+6.0.3790.1830+ready+at++Thu,+1+Jun+2006+20:53:08+-0500+ 0 0 118 0 31 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionCommand SMTPSVC1 SERVER-B - 25 HELO - domain-b.com 0 0 4 0 31 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionResponse SMTPSVC1 SERVER-B - 25 - - 250+domain-a.com+Hello+[yy.yy.yyy.yy] 0 0 43 0 63 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionCommand SMTPSVC1 SERVER-B - 25 MAIL - FROM:<Administrator@domain-b.com> 0 0 4 0 94 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionResponse SMTPSVC1 SERVER-B - 25 - - 250+2.1.0+Administrator@domain-b.com....Sender+OK 0 0 47 0 141 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionCommand SMTPSVC1 SERVER-B - 25 RCPT - TO:<receiving-email@domain-a.com> 0 0 4 0 141 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionResponse SMTPSVC1 SERVER-B - 25 - - 250+2.1.5+receiving-email@domain-a.com+ 0 0 37 0 156 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionCommand SMTPSVC1 SERVER-B - 25 DATA - - 0 0 4 0 172 SMTP - - - -
2006-06-02 01:53:08 xx.xxx.xxx.xx OutboundConnectionResponse SMTPSVC1 SERVER-B - 25 - - 354+Start+mail+input;+end+with+<CRLF>.<CRLF> 0 0 44 0 188 SMTP - - - -

Andy.
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aaskewAuthor Commented:
Note, The above is logged with the sending server configured to send HELO instead of EHLO.

Thanks,
Andy.
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BembiCEOCommented:
Ups, this looks like a problem we had some time before.

Just check the following:
1.) Enable EHLO again and check the log if something changes - send the log sequence here...
2.) Send a few mails in different format, i.e. HTML, RTF, Plain text.
3.) Check if both servers are using the same service pack level.

Is there any AntiVirus software or SPAM detection software running on one of the servers (esp. the sending one). We experienced some issues looking like your problem with AntiVirus software, which did not allow to send HTML messages with the same result (missing QUIT).
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