sending mail through exchange to postfix on a subdomain

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My current setup looks something like this:

mail.example.com:25->CiscoPIX->(network)->exchange.int.example.com(192
..168.101.18):25

The dns server has MX records for example.com being mail.example.com
(sdsl) and mail2.example.com (backup satalite connection).
Also residing on the internal network is linux.int.cardow.com
(192.168.101.19), which has it's own corresponding MX record.
nslookup of the MX/A records on the exchange server produces the
expected results, and I can telnet linux.int.example.com 25, and get
the Postfix banner.
Yet when I try to send mail from Outlook to
user@linux.int.cardow.com, I immediately get an error response "A
configuration error in the e-mail system caused the message to bounce
between two servers or to be forwarded between two recipients." No
connection attempt is ever made to linux.int.example.com. I get the
same error when trying to email user@192.168.101.19.
I've been through just about every setting on the exchange server I
can think of, but can't find why it is not sending the mail to the
linux server. The Recipient Policy has only SMTP entries, example.com
and int.example.com. There are no settings for specific mail routing
or smarthosts. There is no firewall between 192.168.101.19 and
192.168.101.18.
Any ideas?

Gavin

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0
gavin8845 (10)
12/8/2004 4:19:51 PM
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"Gavin Hanover" <gavin@subnets.org> wrote:

					[ snip ]

>Yet when I try to send mail from Outlook to
>user@linux.int.cardow.com, I immediately get an error response "A
>configuration error in the e-mail system caused the message to bounce
>between two servers or to be forwarded between two recipients." 

Is that address assigned to a Contact, or a mail-enabled user, in the
AD? If so, what's the value of that object's targetAddress?


-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/9/2004 2:14:56 AM
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"Rich Matheisen [MVP]" <richnews@rmcons.com.NOSPAM.COM> wrote in
message news:45dfr05v134rdd7c85lv910b9rs9bvpoja@4ax.com...
: "Gavin Hanover" <gavin@subnets.org> wrote:
:
: [ snip ]
:
: >Yet when I try to send mail from Outlook to
: >user@linux.int.cardow.com, I immediately get an error response "A
: >configuration error in the e-mail system caused the message to
bounce
: >between two servers or to be forwarded between two recipients."
:
: Is that address assigned to a Contact, or a mail-enabled user, in
the
: AD? If so, what's the value of that object's targetAddress?


i've tried it both putting the address in the to: field, and creating
an AD contact. the AD contact has an E-mail field as
SMTP:user@linux.int.example.com, and i've tried both with and without
a second smtp address of user@example.com. there is an exchange
e-mail address on the contact, as there is on all the other contacts
we have in AD which work just fine (all other contacts are outside
our domain).

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0
gavin8845 (10)
12/9/2004 12:25:25 PM
"Gavin Hanover" <gavin@subnets.org> wrote:

					[ snip ]

>i've tried it both putting the address in the to: field, and creating
>an AD contact. the AD contact has an E-mail field as
>SMTP:user@linux.int.example.com, and i've tried both with and without
>a second smtp address of user@example.com. there is an exchange
>e-mail address on the contact, as there is on all the other contacts
>we have in AD which work just fine (all other contacts are outside
>our domain).

Do you see the same behavior if you use, say, Outlook Express to send
that message (using your Exchange server as the SMTP server)?

Using Outlook, when you enter the SMTP address into the "To:" header
and press Ctrl+K, does the address change to show you a display name
or does the SMTP address simply get underlined?

Is it possible you have the address in Outlook's "Contacts" folder?

The error you're getting indicates that the categorizer sees that
address as belonging to the Exchange organization and there's no
mailbox to receive the message.

-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/9/2004 3:29:33 PM
Gavin,

Since you are using PIX, the default behaviour in PIX is NOT to allow an internal machine connect to an Outside 
interface. What does your MX resolve to - Internal or External IP?

If it is external IP, you probably won't be able to connect from an internal machine unless you have an 'alias' command 
setup in PIX. Try opening a telnet session to mail.example.com rather than 192.168.101.18.


Regards,
Jimmy.

Gavin Hanover wrote:

> -----BEGIN PGP SIGNED MESSAGE-----
> Hash: SHA1
> 
> My current setup looks something like this:
> 
> mail.example.com:25->CiscoPIX->(network)->exchange.int.example.com(192
> .168.101.18):25
> 
> The dns server has MX records for example.com being mail.example.com
> (sdsl) and mail2.example.com (backup satalite connection).
> Also residing on the internal network is linux.int.cardow.com
> (192.168.101.19), which has it's own corresponding MX record.
> nslookup of the MX/A records on the exchange server produces the
> expected results, and I can telnet linux.int.example.com 25, and get
> the Postfix banner.
> Yet when I try to send mail from Outlook to
> user@linux.int.cardow.com, I immediately get an error response "A
> configuration error in the e-mail system caused the message to bounce
> between two servers or to be forwarded between two recipients." No
> connection attempt is ever made to linux.int.example.com. I get the
> same error when trying to email user@192.168.101.19.
> I've been through just about every setting on the exchange server I
> can think of, but can't find why it is not sending the mail to the
> linux server. The Recipient Policy has only SMTP entries, example.com
> and int.example.com. There are no settings for specific mail routing
> or smarthosts. There is no firewall between 192.168.101.19 and
> 192.168.101.18.
> Any ideas?
> 
> Gavin
> 
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> 2gNmm/4vku0VQWBtqwqwslNg
> =XJ7N
> -----END PGP SIGNATURE-----
> 
> 

0
anonymous (74722)
12/9/2004 7:30:29 PM
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That might be the case if I was going from linux.int.example.com to
the exchange server using an @example.com address, but a mail sent to
@linux.int.example.com does not touch the PIX. Even so, linux.int has
an entry in /etc/hosts to resolve mail.example.com to 192.168.101.18.

Gavin

"Anonymous" <Anonymous@discussions.microsoft.com> wrote in message
news:e06wlWi3EHA.3452@TK2MSFTNGP10.phx.gbl...
: Gavin,
:
: Since you are using PIX, the default behaviour in PIX is NOT to
allow an internal machine connect to an Outside
: interface. What does your MX resolve to - Internal or External IP?
:
: If it is external IP, you probably won't be able to connect from an
internal machine unless you have an 'alias' command
: setup in PIX. Try opening a telnet session to mail.example.com
rather than 192.168.101.18.
:
:
: Regards,
: Jimmy.

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0
gavin8845 (10)
12/13/2004 1:58:20 PM
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$ telnet 192.168.101.18 25
Trying 192.168.101.18...
Connected to 192.168.101.18.
Escape character is '^]'.
220 mail.example.com Microsoft ESMTP MAIL Service, Version:
6.0.3790.211 ready at
  Mon, 13 Dec 2004 09:57:42 -0400
HELO mail
250 mail.example.com Hello [192.168.101.248]
mail from: gavin@example.com
250 2.1.0 gavin@example.com....Sender OK
rcpt to: rt@linux.int.example.com
250 2.1.5 rt@linux.int.example.com
data
354 Start mail input; end with <CRLF>.<CRLF>
Subject: test

test
..
250 2.6.0 <NMSelkkOO1Spm7jsGwP00000be3@mail.example.com> Queued mail
for delivery

quit
221 2.0.0 mail.example.com Service closing transmission channel
Connection closed by foreign host.

$

Same error message get's returned to me:

Microsoft Mail Internet Headers Version 2.0
From: postmaster@example.com
To: Gavin@example.com
Date: Mon, 13 Dec 2004 09:58:11 -0400
MIME-Version: 1.0
Content-Type: multipart/report; report-type=delivery-status;
 boundary="9B095B5ADSN=_01C4BE9D0E13B6B500005CDEmail.example.com"
X-DSNContext: 7ce717b1 - 1383 - 00000002 - C00402CF
Message-ID: <j0fcxDRIM000006af@mail.example.com>
Subject: Delivery Status Notification (Failure)

- --9B095B5ADSN=_01C4BE9D0E13B6B500005CDEmail.example.com
Content-Type: text/plain; charset=unicode-1-1-utf-7

- --9B095B5ADSN=_01C4BE9D0E13B6B500005CDEmail.example.com
Content-Type: message/delivery-status

- --9B095B5ADSN=_01C4BE9D0E13B6B500005CDEmail.example.com
Content-Type: message/rfc822

Received: from mail ([192.168.101.248]) by mail.example.com with
Microsoft SMTPSVC(6.0.3790.211);
  Mon, 13 Dec 2004 09:58:05 -0400
Subject: test
From: gavin@example.com
Bcc:
Return-Path: gavin@example.com
Message-ID: <NMSelkkOO1Spm7jsGwP00000be3@mail.example.com>
X-OriginalArrivalTime: 13 Dec 2004 13:58:10.0935 (UTC)
FILETIME=[C804F070:01C4E11B]
Date: 13 Dec 2004 09:58:10 -0400


- --9B095B5ADSN=_01C4BE9D0E13B6B500005CDEmail.example.com--


Your message did not reach some or all of the intended recipients.

      Subject: test
      Sent: 12/13/2004 9:58 AM

The following recipient(s) could not be reached:

      support test on 12/13/2004 9:58 AM
            A configuration error in the e-mail system caused the
message to bounce between two servers or to be forwarded between two
recipients.  Contact your administrator.
            <mail.example.com #5.3.5>



Same thing happens when i use rt@192.168.101.19, as well.


Gavin
"Rich Matheisen [MVP]" <richnews@rmcons.com.NOSPAM.COM> wrote in
message news:brpgr0lnqfl8apr6b6sih344s4u3ls54u2@4ax.com...
: "Gavin Hanover" <gavin@subnets.org> wrote:
:
: [ snip ]
:
: >i've tried it both putting the address in the to: field, and
creating
: >an AD contact. the AD contact has an E-mail field as
: >SMTP:user@linux.int.example.com, and i've tried both with and
without
: >a second smtp address of user@example.com. there is an exchange
: >e-mail address on the contact, as there is on all the other
contacts
: >we have in AD which work just fine (all other contacts are outside
: >our domain).
:
: Do you see the same behavior if you use, say, Outlook Express to
send
: that message (using your Exchange server as the SMTP server)?
:
: Using Outlook, when you enter the SMTP address into the "To:"
header
: and press Ctrl+K, does the address change to show you a display
name
: or does the SMTP address simply get underlined?
:
: Is it possible you have the address in Outlook's "Contacts" folder?
:
: The error you're getting indicates that the categorizer sees that
: address as belonging to the Exchange organization and there's no
: mailbox to receive the message.
:
: -- 
: Rich Matheisen
: MCSE+I, Exchange MVP
: MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm

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0
gavin8845 (10)
12/13/2004 2:08:05 PM
"Gavin Hanover" <gavin@subnets.org> wrote:


Based on this, I'm going to say that you have the SMTP address in your
AD somewhere, either on a Contact or a mail-enabled user. For the
system to do this the address must be assigned to an object that canot
accept delivery of the message and is probably trying to send the
message to itself.

Try running LDP.exe and search the domain using a scope of "subtree"
and this "Filter":

   anr=rt@linux.int.example.com

and then

   proxyaddresses=smtp:rt@linux.int.example.com

And see if you can find that address.

-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/14/2004 4:44:23 AM
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I believe I mentioned in my first post, that there was a contact in
AD with the SMTP address set to rt@linux.int.example.com. I have
since deleted it, and I still get errors when attempting to send mail
to rt@linux.int.example.com and rt@192.168.101.19 (which AD has never
had as a parameter anywhere). Searching LDP produces the following:

- -----------
***Searching...
ldap_search_s(ld, "DC=int,DC=example,DC=com", 2, "(anr=rt@*)",
attrList,  0, &msg)
Result <0>: (null)
Matched DNs:
Getting 0 entries:
- -----------
***Searching...
ldap_search_s(ld, "DC=int,DC=example,DC=com", 2,
"(anr=rt@linux.int.example.com)", attrList,  0, &msg)
Result <0>: (null)
Matched DNs:
Getting 0 entries:
- -----------
***Searching...
ldap_search_s(ld, "DC=int,DC=example,DC=com", 2,
"(proxyaddress=smtp:rt@*)", attrList,  0, &msg)
Result <0>: (null)
Matched DNs:
Getting 0 entries:
- -----------
***Searching...
ldap_search_s(ld, "DC=int,DC=example,DC=com", 2,
"(proxyaddress=smtp:*linux*)", attrList,  0, &msg)
Result <0>: (null)
Matched DNs:
Getting 0 entries:
- -----------
***Searching...
ldap_search_s(ld, "DC=int,DC=example,DC=com", 2,
"(proxyaddress=smtp:rt@linux.int.example.com)", attrList,  0, &msg)
Result <0>: (null)
Matched DNs:
Getting 0 entries:
- -----------



"Rich Matheisen [MVP]" <richnews@rmcons.com.NOSPAM.COM> wrote in
message news:d3rsr0laekijhao0lobsn3j97h5372jdef@4ax.com...
: "Gavin Hanover" <gavin@subnets.org> wrote:
:
:
: Based on this, I'm going to say that you have the SMTP address in
your
: AD somewhere, either on a Contact or a mail-enabled user. For the
: system to do this the address must be assigned to an object that
canot
: accept delivery of the message and is probably trying to send the
: message to itself.
:
: Try running LDP.exe and search the domain using a scope of
"subtree"
: and this "Filter":
:
:   anr=rt@linux.int.example.com
:
: and then
:
:   proxyaddresses=smtp:rt@linux.int.example.com
:
: And see if you can find that address.
:
: -- 
: Rich Matheisen
: MCSE+I, Exchange MVP
: MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm

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0
gavin8845 (10)
12/14/2004 9:35:58 PM
"Gavin Hanover" <gavin@subnets.org> wrote:

>I believe I mentioned in my first post, that there was a contact in
>AD with the SMTP address set to rt@linux.int.example.com. 

Yes, you did. I apoloize for not being more specific. What I wanted
you to look for was a Contact or mail-enabled user with a
targetAddress in your own domain that had the address in question as a
secondary SMTP proxy address.

>I have
>since deleted it, and I still get errors when attempting to send mail
>to rt@linux.int.example.com and rt@192.168.101.19 (which AD has never
>had as a parameter anywhere). Searching LDP produces the following:

Then it's time to crank up the diagnostics logging level on the
MSExchangeTransport service. I'd start with the Categorizer and SMTP
Protocol categories.

-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/14/2004 10:14:50 PM
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

Event Type: Error
Event Source: MSExchangeTransport
Event Category: NDR
Event ID: 3017
Date:  12/17/2004
Time:  9:58:11 AM
User:  N/A
Computer: NMS
Description:
A non-delivery report with a status code of 5.3.5 was generated for
recipient rfc822;rt@linux.int.example..com (Message-ID
<NMSi4I2vXwv63Ys3AQC00000cee@mail.example.com>).
Causes: A looping condition was detected. (The server is configured
to route mail back to itself). If you have multiple SMTP Virtual
Servers configured on your Exchange server, make sure they are
defined by a unique incoming port and that the outgoing SMTP port
configuration is valid to avoid looping between local virtual
servers.
Solution: Check the configuration of the virtual server�s connectors
for loops and ensure each virtual server is defined by a unique
incoming port.

For more information, see Help and Support Center at
http://go.microsoft.com/fwlink/events.asp.
Data:
0000: cf 02 04 c0               �..�



There is only one Default SMTP Virtual Server, and one Internet Mail
SMTP Connector.


"Rich Matheisen [MVP]" <richnews@rmcons.com.NOSPAM.COM> wrote in
message news:61pur0dq8l9udn0ebrqv63259vnk4qstof@4ax.com...
: "Gavin Hanover" <gavin@subnets.org> wrote:
:
: >I believe I mentioned in my first post, that there was a contact
in
: >AD with the SMTP address set to rt@linux.int.example.com.
:
: Yes, you did. I apoloize for not being more specific. What I wanted
: you to look for was a Contact or mail-enabled user with a
: targetAddress in your own domain that had the address in question
as a
: secondary SMTP proxy address.
:
: >I have
: >since deleted it, and I still get errors when attempting to send
mail
: >to rt@linux.int.example.com and rt@192.168.101.19 (which AD has
never
: >had as a parameter anywhere). Searching LDP produces the
following:
:
: Then it's time to crank up the diagnostics logging level on the
: MSExchangeTransport service. I'd start with the Categorizer and
SMTP
: Protocol categories.
:
: -- 
: Rich Matheisen
: MCSE+I, Exchange MVP
: MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm

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0
gavin8845 (10)
12/17/2004 2:21:07 PM
"Gavin Hanover" <gavin@subnets.org> wrote:

>Event Type: Error
>Event Source: MSExchangeTransport
>Event Category: NDR
>Event ID: 3017
>Date:  12/17/2004
>Time:  9:58:11 AM
>User:  N/A
>Computer: NMS
>Description:
>A non-delivery report with a status code of 5.3.5 was generated for
>recipient rfc822;rt@linux.int.example..com 
                                      ^^
What's up with the two consecutive periods in that SMTP address?


>(Message-ID
><NMSi4I2vXwv63Ys3AQC00000cee@mail.example.com>).
>Causes: A looping condition was detected. (The server is configured
>to route mail back to itself). 

That seems pretty clear.

You've already stated (I think) that the MX and A records for the
domain in question are correct and that running NSLOOKUP from the
Exchange server returns the expected results, so the problem's got to
be in the way you have things configured.

					[ snip ]

>There is only one Default SMTP Virtual Server, and one Internet Mail
>SMTP Connector.

And what's on the "Address Space" tab of that SMTP Connector?

If you have only one SMTP Virtual Server in the organization, remove
the SMTP Connector and see what happens. If it's the SMTP connector
that's causing the problem then the problem shold disappear.


-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/18/2004 2:19:05 AM
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

sorry for the delayed response, other work issues took priority.

"Rich Matheisen [MVP]" <richnews@rmcons.com.NOSPAM.COM> wrote in
message news:0a47s0d714jg4mcmunoo2d4cmikqrke56q@4ax.com...
: "Gavin Hanover" <gavin@subnets.org> wrote:
:
: >Event Type: Error
: >Event Source: MSExchangeTransport
: >Event Category: NDR
: >Event ID: 3017
: >Date:  12/17/2004
: >Time:  9:58:11 AM
: >User:  N/A
: >Computer: NMS
: >Description:
: >A non-delivery report with a status code of 5.3.5 was generated
for
: >recipient rfc822;rt@linux.int.example..com
:                                      ^^
: What's up with the two consecutive periods in that SMTP address?

i'm replacing hostnames manually to keep somewhat of anonymity wrt
company name. so that's a typo on my part.

: [ snip ]
:
: >There is only one Default SMTP Virtual Server, and one Internet
Mail
: >SMTP Connector.
:
: And what's on the "Address Space" tab of that SMTP Connector?

SMTP * 1

: If you have only one SMTP Virtual Server in the organization,
remove
: the SMTP Connector and see what happens. If it's the SMTP connector
: that's causing the problem then the problem shold disappear.

And this won't have any affect on internet delivery, right? (sorry if
this is basic, work isn't paying for MCSE till next year)

Gavin

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0
gavin8845 (10)
12/22/2004 6:14:38 PM
"Gavin Hanover" <gavin@subnets.org> wrote:

					[ snip ]

>: >There is only one Default SMTP Virtual Server, and one Internet
>Mail
>: >SMTP Connector.
>:
>: And what's on the "Address Space" tab of that SMTP Connector?
>
>SMTP * 1

Good. :)


>: If you have only one SMTP Virtual Server in the organization,
>remove
>: the SMTP Connector and see what happens. If it's the SMTP connector
>: that's causing the problem then the problem shold disappear.
>
>And this won't have any affect on internet delivery, right? (sorry if
>this is basic, work isn't paying for MCSE till next year)

That's correct. With only a single VS the need for a SMTP Connector is
only for control over delivery restrictions, and other things you'r
probably not using.

-- 
Rich Matheisen
MCSE+I, Exchange MVP
MS Exchange FAQ at http://www.swinc.com/resource/exch_faq.htm
0
richnews (7316)
12/22/2004 9:39:37 PM
-----BEGIN PGP SIGNED MESSAGE-----
Hash: SHA1

: >: If you have only one SMTP Virtual Server in the organization,
: >remove
: >: the SMTP Connector and see what happens. If it's the SMTP
connector
: >: that's causing the problem then the problem shold disappear.
: >
: >And this won't have any affect on internet delivery, right? (sorry
if
: >this is basic, work isn't paying for MCSE till next year)
:
: That's correct. With only a single VS the need for a SMTP Connector
is
: only for control over delivery restrictions, and other things you'r
: probably not using.

Ok, removed the SMTP connector, still get the same error.

any other suggestions?

Gavin

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gavin8845 (10)
12/23/2004 4:35:19 PM
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