Gmail did not encrypt this message

[lucianobraz]

When I receive an email from my domain, I have a red text in gmail, with the following message: did not encrypt this message

I think it has to do with the TLS configuration, can someone help me.

 

[Stoiko Ivanov]

share the screenshot of the "red text" and the logs of the mail.
usually enabling TLS is done in GUI->Configuration->Mail Proxy->TLS

 

[lucianobraz]

Please see the attached prints.

 

[Stoiko Ivanov]

please share the logs of the mail - and the Received headers
* The settings would indicate that PMG should use encryption (you might try to reboot the PMG just in case and retry)
* make sure PMG sends the mails directly to gmail (if you have a smart-host configured or this is an inbound mail and you have a transport) the encryption might be lost there...

 

[lucianobraz]

Delivered-To: brasluciano@gmail.com
Received: by 2002:a17:522:5ace:b0:571:9403:140b with SMTP id e14csp2404454pvk;
Wed, 21 Feb 2024 05:49:11 -0800 (PST)
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ARC-Authentication-Results: i=1; mx.google.com;
dkim=temperror (no key for signature) header.i=@prodel.co.ao header.s=default header.b=cXgnq8ol;
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spf=pass (google.com: domain of luciano.braz@prodel.co.ao designates 105.174.4.252 as permitted sender) smtp.mailfrom=luciano.braz@prodel.co.ao;
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From: Luciano Braz <luciano.braz@prodel.co.ao>
To: Luciano Bras <brasluciano@gmail.com>
Subject: test1
Thread-Topic: test1
Thread-Index: AQHaZMxADo0wUjVttkyIIc0uhcWI/Q==
Date: Wed, 21 Feb 2024 13:45:38 +0000
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[Stoiko Ivanov]

hm - ok from the received headers it seems as if PMG directly sent this to gmail:
* please share the logs

however I checked the mx record of your domain - and it seems at least inbound it's not directly a PMG
so just to be on the safe side - do you maybe have some kind of content inspecting firewall in front of PMG?
the EHLO reply from the mx brought me to some cisco support sites:
https://www.limilabs.com/qa/1897/problem-connecting-through-smtp
https://www.cisco.com/c/en/us/support/docs/security/email-security-appliance/118550-qa-esa-00.html

 

[lucianobraz]

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In-Reply-To: <8c96ba40b6e24737846ba153518679ca@SVLDCCEXP02.Prodel.local>
From: Luciano Bras <brasluciano@gmail.com>
Date: Tue, 20 Feb 2024 21:19:24 +0000
Message-ID: <CAD6mbtfP9M3F54pxwokok7SPzWsKyhg+tDMwyAzShnCpE-DBfA@mail.gmail.com>
Subject: Re: Tes
To: Luciano Braz <luciano.braz@prodel.co.ao>
Content-Type: multipart/alternative; boundary="0000000000006715510611d6c48c"
X-SPAM-LEVEL: Spam detection results: 0
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FREEMAIL_FROM 0.001 Sender email is commonly abused enduser mail provider
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