Hi Team

Please feel free to let me know this was not a suitable question for this
list, apologies in advance if so.

At $dayjob one of my fairly new staff forwarded me a bounce message from
gmail for an outbound email we were sending to a supplier.

Headers are down at the end of the email but the bounce message was:
554 5.0.0 <gmail-smtp-in.l.google.com #5.0.0 smtp; 550-5.7.1 [185.201.19.76
14] Messages missing a valid address in From: 550 5.7.1 header, or having
no From: header, are not accepted.
l6-20020a05600c2cc600b0039423b63859si6456162wmc.204 - gsmtp>

A test email sent from the same system to my own emails (hosted by gmail)
didn't receive a bounce back so I am of the feeling there must be a From:
header being included correctly in the message. So trying to investigate
the header as to why it may not be a valid address and I was hoping for
some assistance / guidance as to if I am interpreting the RFC correctly as
to validity or am I barking up the wrong tree entirely.

The user whose email bounced has a last name with an accented character
which is not a valid ASCII printable character and if I am reading RFC 6854
S2.1 and RFC 5322 S2.2 correctly the header field must contain printable
ASCII code points (and a couple of allowed other characters in the header
field body.

I did note that the from header in the bounced email was shown as:

=?utf-8?b?IkZlcm5hbmRvIFNhbnRvcyBEZSBTw6EiIDxmZXJuYW5kby5zQGdsLmNvLm56?=

=?utf-8?b?Pg==?=
Converting this from Base64 encoded UTF-8 into plain UTF-8 I see the string:
"Fernando Santos De Sá" <fernand...@gl.co.nz>
Which is correct for my user (however obviously not ASCII.

A few questions
Have I correctly identified the issue (or most likely issue) triggering
this message from gmail?
Is there a good document for guidance on catching invalid values (including
UTF-8 strings) and how they should be handled for headers in email (I see
in RFC 5322 S3.2.4 there is an allowance for quoted strings that allow
characters that are other than allowed in atoms but I guess if that was
valid for what I was generating above the email wouldn't have bounced -
possibly an issue because the whole string was Base64 encoded?) so I can
look to catch situations that are problematic in future and provide a
generalized system?
Does anyone have any guidance on other situations they have hit with email
systems rejecting what is often accepted so I can try to generally test for
known "fun interactions" and handle them?

(noting these emails are generated out of our in house developed operations
management system so its my code that did the wrong thing originally here
and what I need to get fixed)

Thank you for your time.

Headers from the bounce:

Notes:
email system isn't currently depositing emails into the sent box so user
receives CC of emails sent on their behalf so they see what has gone out
antispamcloud is our spam filter provider who scans all inbound and
outbound emails but error message was generated by gmail when trying to
hand off the email. Providers web portal for checking message status
decoded source email address and name string.

Original message headers:

Return-Path: <fernand...@gl.co.nz>

Received: from gl-ex02.gl.co.nz ([45.118.188.115])

        by mx262.antispamcloud.com with esmtps
(TLSv1.2:ECDHE-RSA-AES128-GCM-SHA256:128)

        (Exim 4.92)

        (envelope-from <fernand...@gl.co.nz>)

        id 1nlMq1-000A9Y-Mo

        for <SUPPLIER EMAIL ADDRESS>; Mon, 02 May 2022 05:35:15 +0200

Received: from GL-EX02.internal.gl.co.nz (192.168.33.22) by

 GL-EX02.internal.gl.co.nz (192.168.33.22) with Microsoft SMTP Server

 (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id

 15.2.1118.7; Mon, 2 May 2022 15:35:02 +1200

Received: from gl-be04.internal.gl.co.nz (192.168.33.37) by

 GL-EX02.internal.gl.co.nz (192.168.33.22) with Microsoft SMTP Server id

 15.2.1118.7 via Frontend Transport; Mon, 2 May 2022 15:35:02 +1200

Content-Type: text/plain

MIME-Version: 1.0

From: =?utf-8?b?IkZlcm5hbmRvIFNhbnRvcyBEZSBTw6EiIDxmZXJuYW5kby5zQGdsLmNvLm56?=

 =?utf-8?b?Pg==?=

To: <SUPPLIER EMAIL ADDRESS>

CC: <fernand...@gl.co.nz>

Subject: Global Jobsheet <INTERNAL REFERENCE NUMBER> - Fixing

Message-ID: <0368d464-ce75-4993-893a-6861eaebc...@gl-ex02.internal.gl.co.nz>

Date: Mon, 2 May 2022 15:35:02 +1200

X-Originating-IP: 45.118.188.115

X-MailAssure-Domain: gl.co.nz

X-MailAssure-Username: 45.118.188.115

Authentication-Results: antispamcloud.com; auth=pass
smtp.auth=45.118.188....@gl.co.nz

X-MailAssure-Outgoing-Class: ham

X-MailAssure-Outgoing-Evidence: Combined (0.09)

X-Recommended-Action: accept

X-Filter-ID: 
Pt3MvcO5N4iKaDQ5O6lkdGlMVN6RH8bjRMzItlySaT/SWj98WPq4CtCgxem7mj3kPUtbdvnXkggZ

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 /Cb06J8uG+dikNJv32G4gfdf

X-Report-Abuse-To: s...@quarantine11.antispamcloud.com

X-Exim-DSN-Information: Due to administrative limits only headers are returned


Regards
Alexander

Alexander Neilson
Neilson Productions Limited

alexan...@neilson.net.nz
021 329 681
022 456 2326
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