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Exchange 2010 530 5.7.1 Client was not authenticated from some MTAs

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  • Exchange 2010 530 5.7.1 Client was not authenticated from some MTAs

    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:

    Code:
    "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:<[email protected]> 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:<[email protected]> SIZE=78604,
    08D0A7BE5BCEFE28;2013-11-04T22:46:04.886Z;1,receiving message
    250 2.1.0 Sender OK,
    RCPT TO:<[email protected]>,
    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 <[email protected]> [InternalId=18696] Queued mail for delivery,
    QUIT,
    221 2.0.0 Service closing transmission channel,
    Real stupidity always beats Artificial Intelligence (c) Terry Pratchett

    BA (BM), RHCE, MCSE, DCSE, Linux+, Network+
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