Thank you! Could you provide an example in which it does not work, and for which it will now work? I'd love to support it, but it is hard for me to verify at the moment that it will improve the situation.

From the linked issue, protonmail recipient accounts would discard attachments sent with yagmail, but with this change they now show up as expected. I tested this by creating a new Protonmail email account and checking attachments in their email web app.

The old header looked like:

Content-Type: text/plain; name*=utf-8''voice_log.txt
MIME-Version: 1.0
Content-Transfer-Encoding: base64

and the new header:

Content-Type: text/plain; name="skills_log.txt"
MIME-Version: 1.0
Content-Disposition: attachment; filename="skills_log.txt"; name="skills_log.txt"
Content-Transfer-Encoding: base64

A sample call might look like:

        with yagmail.SMTP("[email protected]", password, "smtp.gmail.com", '465') as yag:
            yag.send(to="[email protected]", subject="Test Attachments, contents="See attached files.",
                     attachments=["/tmp/test_attach.log"])

@kootenpv Anything else I can contribute here to help get this merged?

Hello,
The ASVS Working Group at OWASP discussed ways to properly encode the Content-Disposition header. It is important to avoid the filename being misused to manipulate other headers. I kinda trust them more to navigate the flow of numerous RFCs around this subject.
OWASP/ASVS#1390

You may also refer to https://blog.nodemailer.com/2017/01/27/the-mess-that-is-attachment-filenames/ who claim you can also set Content-Type... name as a fallback value for legacy MUAs.

EDIT: Sorry, RFC 6266 is standard for HTTP. The relevant one for MTA is still RFC 2231 AFAICT. See CVE-2024-39929 for an example on how the header could be abused to send attachments with malicious names.