On 2 Dec 2015, at 12:28, Bill Cole wrote:

On 2 Dec 2015, at 10:42, Bryan K. Walton wrote:

We've got a postfix mail server running postscreen that is configured to make use of the postscreen_dnsbl_whitelist_threshold feature. The postfix version is 3.0.3. Things have been working really well for the last 6 months, or so. However, we have recently discovered an issue where it seems that incoming email that comes from *.outbound.protection.outlook.com servers seem to not be handled properly.
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Questions:
1. Why is this message getting a 450 message? Is the outlook mail server speaking out of turn here?

Since you didn't bother providing 'postconf -n' output, which would provide useful clues, we are left with making random guesses...

My random guess: you're doing sender verification. Don't. It's broken in concept and especially broken operationally if you want to communicate with people using MS products.

Alternative (and I think better) random guess: you've enabled one or more "after 220 server greeting" test. See the postscreen man page for the consequences of such configuration and note that there's no law requiring retry delivery of a deferred message to be done via the same IP as any prior delivery attempt, and a big complex mail system built for high availability is likely to NOT do so.

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