On 4/21/20 2:15 AM, Mike Gabriel via Mailman-Developers wrote:
> Hi all,
> 
> I have a special case in a 3.3.0 Mailman3 instance.
> 
> One of our users uses AppleMail and sends a mail with PDF attachment to
> a mailing list with the following settings in Postorius:
> 
>    [x] filter content
>    [x] collapse alternatives
>    [x] convert html to plaintext
> 
> However, the PDF is not getting delivered to the mailing list
> recipients. It gets stripped off.


I see the issue.


> The mail structure of the original mail is this:

Summarized

multipart/alternative
    text/plain
    multipart/mixed
        text/html
        application/pdf
        text/html

So the issue is the Apple Mail user is composing the message in rich
text (HTML) format and drags and drops the PDF in the middle of the
message body. Apple Mail then makes the

    multipart/mixed
        text/html
        application/pdf
        text/html

message part [1] and finally makes the text/plain alternative that
doesn't include the PDF.

Since your content filtering is set to collapse alternatives, only the
text/plain first alternative part goes to the list.

I'm not that familiar with Apple Mail, but there may be a way for the
user to 'attach' the PDF rather than dropping it into the message body
and that may work.


[1] This message part will actually be displayed as composed only by an
Apple Mail client, but that's another issue - part of "if you don't ask
to interoperate with anything outside the Apple ecosystem, everything
will be fine".


-- 
Mark Sapiro <m...@msapiro.net>        The highway is for gamblers,
San Francisco Bay Area, California    better use your sense - B. Dylan

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