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Can't send e-mail from Exchange to an internal SMTP server

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Can't send e-mail from Exchange to an internal SMTP server - 31.Jan.2008 4:32:13 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

Hi,

The situation is that I have an Exchange 2003 server, and another server with SMTP virtual server (not running Exchange), both of which are on my LAN. Both servers are running Windows Server 2003.

The proiblem is that I cannot send e-mails from the Exchange server to the other internal server. The just sit queued up retrying to send.

Using telnet or Outlook I can send e-mails to the other internal server successfully and they go into the drop folder as they should do.

Using the Microsoft SMTP diag tool I get the following results...

Searching for Exchange external DNS settings.
Computer name is MSL-MAILSERVER1.
VSI 1 has the following external DNS servers:
There are no external DNS servers configured.

Checking SOA for msl-sharepoint.mixingsolutions.co.uk.
Checking external DNS servers.
Checking internal DNS servers.
SOA serial number match: Passed.

Checking local domain records.
Checking MX records using TCP: mixingsolutions.com.
Checking MX records using UDP: mixingsolutions.com.
Both TCP and UDP queries succeeded. Local DNS test passed.

Checking remote domain records.
Checking MX records using TCP: msl-sharepoint.mixingsolutions.co.uk.
Checking MX records using UDP: msl-sharepoint.mixingsolutions.co.uk.
Both TCP and UDP queries succeeded. Remote DNS test passed.

Checking MX servers listed for test@msl-sharepoint.mixingsolutions.co.uk.
Connecting to msl-sharepoint.mixingsolutions.co.uk [192.168.99.9] on port 25.
Failed to receive data. Error: 10060
Error: Expected "250". Failed to get a response from the server.
Failed to submit mail to msl-sharepoint.mixingsolutions.co.uk.

... I've racked my brain and can think of no reason why this would ben happening ?. Can anyone help ?.

Thanks.

< Message edited by Fatboy40 -- 31.Jan.2008 4:33:25 AM >

Post #: 1

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RE: Can't send e-mail from Exchange to an internal SMTP... - 31.Jan.2008 7:30:05 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

Update...

Searching this forum I discovered a Microsoft tool that I was not aware of...

ExTRA

... which I have now used and has highlighted the following problem...

Mail acceptance failure.

XXX failed the mail acceptance test. MAIL FROM command: Respond = Remote socket is not available.

... I suppose all this confirms is what I allready know in that the my other internal server is just not accepting e-mail from my Exchange server, I just don't know why ?.

< Message edited by Fatboy40 -- 31.Jan.2008 7:31:08 AM >

(in reply to Fatboy40)

Post #: 2

RE: Can't send e-mail from Exchange to an internal SMTP... - 31.Jan.2008 10:33:50 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

Looking more at how ExTRA works I noticed that it queries the remote SMTP server in a very specifc way and when sending the EHLO command it will mark the test as having failed if it does not get back either of the following...

250-X-LINK2STATE

or

250- XEXCH50

... howevr, when I query the remote SMTP I only get the following from an EHLO command...

250-AUTH GSSAPI NTLM LOGIN
250-AUTH=LOGIN
250-TURN
250-SIZE 2097152
250-ETRN
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-VRFY
250 OK

... is this the problem ?.

(in reply to Fatboy40)

Post #: 3

RE: Can't send e-mail from Exchange to an internal SMTP... - 31.Jan.2008 9:28:37 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline

For both servers, check the Default SMTP Virtual Server properties. Go to the Access tab and click Relay. For both servers, make sure that the checkbox "Allow all computers which successfully authenticate to relay, regardless of the list above" is checked.

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to Fatboy40)

Post #: 4

RE: Can't send e-mail from Exchange to an internal SMTP... - 1.Feb.2008 3:08:14 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

Hi uemurad,

Yep, the checkbox you mention is checked, I think that this being checked is also the default setting for a SMTP Virtual Server ?.

Thanks.

(in reply to uemurad)

Post #: 5

RE: Can't send e-mail from Exchange to an internal SMTP... - 1.Feb.2008 9:51:17 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline

Yes, that is the default, but unchecking it will disrupt internal communications between Exchange servers.

You are also correct in that Exchange expects one of those responses. The LSA generates the 250-X-LINK2STATE response. Are the two servers in the same routing group?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to Fatboy40)

Post #: 6

RE: Can't send e-mail from Exchange to an internal SMTP... - 1.Feb.2008 10:01:49 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

Hi uemurad,

They are not in the same routing group, only one of the servers is an Exchange server, the other server is just a Windows Server 2003 server with SMTP Virtual Server setup on it.

Exchange just not send e-mails to it (MX records etc have been setup on the internal DNS server)

Thanks.

(in reply to uemurad)

Post #: 7

RE: Can't send e-mail from Exchange to an internal SMTP... - 1.Feb.2008 12:00:31 PM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline

Sorry, I got sidetracked by a couple of the points you made and didn't read the first message closely enough.

When Exchange communicates with a non-Exchange server, it doesn't require the 250-X-LINK2STATE or 250-XEXCH50 responses. This is the way it would function if it communicated with an outside server.

Let's take a step backwards. Is the non-Exchange server supposed to accept mail for an SMTP domain that is different from the one(s) your Exchange server accepts?

If you use Message Tracking to view the outbound message, what does it say?

Is the queue where the message ends up the name of the other domain?

If you telnet to the other server via port 25, what does the initial response say?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to Fatboy40)

Post #: 8

RE: Can't send e-mail from Exchange to an internal SMTP... - 4.Feb.2008 3:24:52 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

quote:

ORIGINAL: uemurad

Sorry, I got sidetracked by a couple of the points you made and didn't read the first message closely enough.

No worries, I probably didn't word it as well as I could have done :)

quote:

ORIGINAL: uemurad

Let's take a step backwards. Is the non-Exchange server supposed to accept mail for an SMTP domain that is different from the one(s) your Exchange server accepts?

Yes, that's correct, is this the root of the problem ?. Should the connector be altered to accomodate this ?.

quote:

ORIGINAL: uemurad

If you use Message Tracking to view the outbound message, what does it say?

The connection was dropped by the remote host

quote:

ORIGINAL: uemurad

Is the queue where the message ends up the name of the other domain?

Yes.

quote:

ORIGINAL: uemurad

If you telnet to the other server via port 25, what does the initial response say?

Exactly what we'd expect, reports SMTP Virual Server version (up to date) and the correct name/domain of the remote server.

Also I've telnet from here, there and everywhere but just finaly got roudn to telneting from the Exchange server, which worked absolutely fine.

So the root of this is more than liekly an Exchnage setting ?.

(in reply to uemurad)

Post #: 9

RE: Can't send e-mail from Exchange to an internal SMTP... - 4.Feb.2008 10:36:13 AM

uemurad

Posts: 8232
Joined: 7.Jan.2004
From: California, USA
Status: offline

quote:

The situation is that I have an Exchange 2003 server, and another server with SMTP virtual server (not running Exchange), both of which are on my LAN. Both servers are running Windows Server 2003.

Do you mean the non-Exchange server does not have Exchange installed? Are you running the SMTP service with IIS?

quote:

Should the connector be altered to accomodate this ?.

The connector should be configured to route the address space (domain). If the connector is being used only for this domain name, it sounds like that part is configured correctly.

Your non-Exchange server is sending back a response to the EHLO command, but how does it respond to the MAIL FROM, RCPT TO and DATA commands?

_____________________________

Regards,

Dean T. Uemura
Microsoft MVP - Exchange (2007-2011)
exchangeguy.blogspot.com
uemurad@yahoo.com

(in reply to Fatboy40)

Post #: 10

RE: Can't send e-mail from Exchange to an internal SMTP... - 5.Feb.2008 3:22:18 AM

Fatboy40

Posts: 20
Joined: 26.Jul.2005
From: U.K.
Status: offline

quote:

ORIGINAL: uemurad

Do you mean the non-Exchange server does not have Exchange installed? Are you running the SMTP service with IIS?

Yep, Exchange is not installed on the internal server I'm trying to send e-mail to, it's just a Windows Server 2003 box with SMTP running with IIS (with a different domain from that of the Exchange server).

quote:

ORIGINAL: uemurad

The connector should be configured to route the address space (domain). If the connector is being used only for this domain name, it sounds like that part is configured correctly.

Your non-Exchange server is sending back a response to the EHLO command, but how does it respond to the MAIL FROM, RCPT TO and DATA commands?

Well, there's a connector setup for our domain that Exchange uses. Do I need to add the 'other' domain as an address space on the same connector ? (or setup a new one ?).

Yep, all SMTP commands are successful. Using telnet from the Exchange server, and on two other machines, I can successfully send e-mails (with a subject + message body etc) to the 'other' internal server running SMTP /IIS.

(in reply to uemurad)

Post #: 11