Dear Fourhundred,

Am 09.08.23 um 07:34 schrieb Fourhundred Thecat via Postfix-users:

my email was flagged as spam by Microsoft.

I have the received email, together with all the headers that Microsoft
added. Specifically the item: X-Microsoft-Antispam-Message-Info:

I have found a tool on github, which attempts to decode this convoluted
item (https://github.com/mgeeky/decode-spam-headers)

And one of the decoded lines says:

(58800400005) - (GUESSING) Somehow related to First Hop server
reputation, it's reverse-PTR resolution or domain impersonation

I am using header rewrite to hide my own IP address, and use localhost
[127.0.0.1] instead. So that the first hop looks like this:

  Received: from [127.0.0.1] (localhost [127.0.0.1]) by mail.xxx.yyy
(Postfix) with ESMTPSA id 7E011B0
         for <a...@bbb.com>; Wed,  9 Aug 2023 07:04:42 +0200 (CEST)

is this considered bad practice?
Or why am I being penalized for this?

All I am trying to achieve is not to disclose from where I am sending my
emails

Sounds like something spammers also would like to do, so it’s considered bad practice. But, it is also not feasible, as the accepting host often logs the IP address. So your strategy would only work, if you use a smarthost (SMTP relay server), deleting the `Received:` records from the header. So the receiver would only see the IP address of the smart host.

As an example for your message to the list from GMX:

    Received: from [10.1.2.16] ([212.25.11.75]) by mail.gmx.net (mrgmx105
[212.227.17.168]) with ESMTPSA (Nemesis) id 1M3DJl-1qWda038fN-003eVr for
     <postfix-users@postfix.org>; Wed, 09 Aug 2023 07:34:49 +0200

mail.gmx.net is the smarthost, and would need to support to not add that Received entry (and remove possible other ones).


Kind regards,

Paul
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