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I have a strange issue on an Exchange 2010 Version: 14.03.0158.001 (latest to date). The receive connector is set up correctly, with anonymous users checked, but still, I can receive mail from some servers (like gmail and some hosts I have access to) both plaintext and TLS, but from some other hosts, that are perfectly legit and support TLS and plaintext too, I get the error in $subject. The logs show the same things I can see if I try to send email manually via telnet.

The only thing that changed recently was a DST switchover yesterday, but the host is set to UTC-7 and seems to be bang on

here's a set of failed and passed comms:

"220 mail.exchange.ca Microsoft ESMTP MAIL Service ready at Mon, 4 Nov 2013 15:44:28 -0700",
EHLO cantsend.com,
250-mail.exchange.ca Hello [1.2.3.4],
250-SIZE 10485760,
250-PIPELINING,
250-DSN,
250-ENHANCEDSTATUSCODES,
250-STARTTLS,
250-AUTH LOGIN,
250-8BITMIME,
250-BINARYMIME,
250 CHUNKING,
MAIL FROM:<admin@cantsend.com> SIZE=1095 BODY=7BIT,
530 5.7.1 Client was not authenticated,

"220 mail.exchange.ca Microsoft ESMTP MAIL Service ready at Mon, 4 Nov 2013 15:46:04 -0700",
EHLO cal1-mh747.smtproutes.com,
250-mail.exchange.ca Hello [192.69.16.69],
250-SIZE 20971520,
250-PIPELINING,
250-DSN,
250-ENHANCEDSTATUSCODES,
250-STARTTLS,
250-AUTH,
250-8BITMIME,
250-BINARYMIME,
250 CHUNKING,
MAIL FROM:<me@mydomain.ca> SIZE=78604,
08D0A7BE5BCEFE28;2013-11-04T22:46:04.886Z;1,receiving message
250 2.1.0 Sender OK,
RCPT TO:<admin@exchange.ca>,
250 2.1.5 Recipient OK,
DATA,
354 Start mail input; end with <CRLF>.<CRLF>,
Tarpit for '0.00:00:31.033' due to 'DelayedAck',Expired;Timeout
250 2.6.0 <B46F5B915084E84BAC41D3121A81073605CCC047@server.mydomain.local> [InternalId=18696] Queued mail for delivery,
QUIT,
221 2.0.0 Service closing transmission channel,
dyasny
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2 Answers2

1

Be aware that connecting from different IPs could land you in different receive connectors.

Check the IP address ranges defined on the network tab of each receive connector (Exchange mangement console > server configuration > hub transport > receive connectors): The failing host / IP address ("[1.2.3.4] " in your example) might be served by a receive connector that is not configured to allow anonymous access.

If you are on the SBS version your check should include all those pre-defined receive connectors, even the one named "SBS fax".

Claus Christensen
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  • Thanks, but I've eliminated this option as the first step. There is only one receive connector active, covering all public IPs, with anonymous access enabled, and I've verified that the failing senders hit it every tie, by simply giving it a unique host identifier name and testing with telnet - I saw the unique hostname at HELO every time – dyasny Nov 05 '13 at 15:14
0

If not your receive connector, did you check your destination addresses for "Sender Restrictions"

example

https://technet.microsoft.com/en-us/library/bb124405(v=exchg.141).aspx

Jacob Evans
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