distribution groups don't deliver to some addresses

I've been trying to create a distribution group that includes both internal and external contacts. I've created all the external contacts as contacts in AD, adding an Exchange email address (SMTP:user@xxxxxxxxxxxxxxxxxx). When sending to this group messages fail to be delivered to some people on the list, it would appear that it won't deliver to hotmail.com, NTL or Wannadoo.

I've checked that the server has a valid PTR on reverse DNS. I@ve checked that the server isn't blacklisted. I also disabled Symantec SMTP checking as I read that some people had solved this problem by doing that, although it hasn't worked in this case.

I've also tried sending emails to those same people individually by just entering their email address and that doesn't get through either.

I've set logging on the SMTP service to 5, but that reports nothing. I've tried SMTPDIAG (attached).

Can any one make any suggestions??

Thanks - John


Searching for Exchange external DNS settings.
Computer name is STORM.
VSI 1 has the following external DNS servers:
217.158.x.x,192.168.2.2

Checking SOA for hotmail.com.
Checking external DNS servers.

Checking TCP/UDP SOA serial number using DNS server [217.158.x.x].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005070501

Checking TCP/UDP SOA serial number using DNS server [192.168.2.2].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005070501
Checking internal DNS servers.

Checking TCP/UDP SOA serial number using DNS server [192.168.2.2].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005070501

Checking TCP/UDP SOA serial number using DNS server [217.158.x.x].
TCP test succeeded.
UDP test succeeded.
Serial number: 2005070501
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: domain.co.uk.
MX: mail1.2nddomain.net (20)
MX: mail.domain.co.uk (10)
A: mail1.2nddomain.net [80.168.x.x]
Checking MX records using UDP: domain.co.uk.
MX: mail1.2nddomain.net (20)
MX: mail.domain.co.uk (10)
A: mail1.2nddomain.net [80.168.x.x]
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: hotmail.com.
MX: mx1.hotmail.com (5)
MX: mx2.hotmail.com (5)
MX: mx3.hotmail.com (5)
MX: mx4.hotmail.com (5)
A: mx1.hotmail.com [65.54.252.99]
A: mx1.hotmail.com [64.4.50.50]
A: mx1.hotmail.com [64.4.50.99]
A: mx1.hotmail.com [65.54.166.99]
A: mx2.hotmail.com [65.54.190.50]
A: mx2.hotmail.com [65.54.252.230]
A: mx2.hotmail.com [65.54.166.230]
A: mx2.hotmail.com [65.54.190.7]
A: mx3.hotmail.com [65.54.167.5]
A: mx3.hotmail.com [65.54.253.99]
A: mx3.hotmail.com [64.4.50.179]
A: mx3.hotmail.com [64.4.50.239]
A: mx4.hotmail.com [65.54.167.230]
A: mx4.hotmail.com [65.54.190.179]
A: mx4.hotmail.com [65.54.190.230]
A: mx4.hotmail.com [65.54.253.230]
Checking MX records using UDP: hotmail.com.
MX: mx1.hotmail.com (5)
MX: mx2.hotmail.com (5)
MX: mx3.hotmail.com (5)
MX: mx4.hotmail.com (5)
Both TCP and UDP queries succeeded. Remote DNS test passed.

Checking MX servers listed for a_hotmail_user@xxxxxxxxxxxx
Connecting to mx4.hotmail.com [65.54.253.230] on port 25.
Received:
220 MC8-F13.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:55:44 -0700


Sent:
ehlo domain.co.uk

Received:
250-MC8-F13.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 MC8-F13.hotmail.com Service closing transmission channel

Successfully connected to mx4.hotmail.com.
Connecting to mx4.hotmail.com [65.54.190.230] on port 25.
Received:
220 mc4-f2.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:55:46 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc4-f2.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc4-f2.hotmail.com Service closing transmission channel

Successfully connected to mx4.hotmail.com.
Connecting to mx4.hotmail.com [65.54.190.179] on port 25.
Connecting to the server failed. Error: 10060
Failed to submit mail to mx4.hotmail.com.
Connecting to mx3.hotmail.com [64.4.50.239] on port 25.
Received:
220 mc3-f14.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:09 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc3-f14.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc3-f14.hotmail.com Service closing transmission channel

Successfully connected to mx3.hotmail.com.
Connecting to mx3.hotmail.com [64.4.50.179] on port 25.
Connecting to the server failed. Error: 10060
Failed to submit mail to mx3.hotmail.com.
Connecting to mx3.hotmail.com [65.54.253.99] on port 25.
Received:
220 mc7-f4.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:32 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc7-f4.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc7-f4.hotmail.com Service closing transmission channel

Successfully connected to mx3.hotmail.com.
Connecting to mx2.hotmail.com [65.54.190.7] on port 25.
Received:
220 mc2-f14.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:33 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc2-f14.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc2-f14.hotmail.com Service closing transmission channel

Successfully connected to mx2.hotmail.com.
Connecting to mx2.hotmail.com [65.54.166.230] on port 25.
Received:
220 mc10-f23.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:34 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc10-f23.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc10-f23.hotmail.com Service closing transmission channel

Successfully connected to mx2.hotmail.com.
Connecting to mx2.hotmail.com [65.54.252.230] on port 25.
Received:
220 MC6-F28.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:36 -0700


Sent:
ehlo domain.co.uk

Received:
250-MC6-F28.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 MC6-F28.hotmail.com Service closing transmission channel

Successfully connected to mx2.hotmail.com.
Connecting to mx1.hotmail.com [65.54.166.99] on port 25.
Received:
220 mc9-f35.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:38 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc9-f35.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc9-f35.hotmail.com Service closing transmission channel

Successfully connected to mx1.hotmail.com.
Connecting to mx1.hotmail.com [64.4.50.99] on port 25.
Received:
220 mc1-f10.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:56:39 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc1-f10.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc1-f10.hotmail.com Service closing transmission channel

Successfully connected to mx1.hotmail.com.
Connecting to mx1.hotmail.com [64.4.50.50] on port 25.
Connecting to the server failed. Error: 10060
Failed to submit mail to mx1.hotmail.com.
Connecting to mx4.hotmail.com [65.54.167.230] on port 25.
Connecting to the server failed. Error: 10060
Failed to submit mail to mx4.hotmail.com.
Connecting to mx3.hotmail.com [65.54.167.5] on port 25.
Received:
220 mc11-f21.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:57:23 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc11-f21.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc11-f21.hotmail.com Service closing transmission channel

Successfully connected to mx3.hotmail.com.
Connecting to mx2.hotmail.com [65.54.190.50] on port 25.
Connecting to the server failed. Error: 10060
Failed to submit mail to mx2.hotmail.com.
Connecting to mx1.hotmail.com [65.54.252.99] on port 25.
Received:
220 mc5-f17.hotmail.com Sending unsolicited commercial or bulk e-mail to Microsoft's computer network is prohibited. Other restrictions are found at http://privacy.msn.com/Anti-spam/. Violations will result in use of equipment located in California and other states. Tue, 12 Jul 2005 06:57:45 -0700


Sent:
ehlo domain.co.uk

Received:
250-mc5-f17.hotmail.com (3.0.1.19) Hello [217.158.189.253]
250-SIZE 29696000
250-PIPELINING
250-8bitmime
250-BINARYMIME
250-CHUNKING
250-AUTH LOGIN
250-AUTH=LOGIN
250 OK


Sent:
mail from: <admin@xxxxxxxxxxxx>

Received:
250 admin@xxxxxxxxxxxxxxxxxxxxxx OK

Sent:
rcpt to: <a_hotmail_user@xxxxxxxxxxx>

Received:
250 a_hotmail_user@xxxxxxxxxxx

Sent:
quit

Received:
221 mc5-f17.hotmail.com Service closing transmission channel

Successfully connected to mx1.hotmail.com.

Relevant Pages