I've experienced this problem last week (and I've seen it 1-2 times before): certain messages would not get posted to the list no matter what, while other messages go through without any problem.
It is similar to what a few others have experienced, including Nicole.

The root of the problem is the symbols that can sneak in ...
Essentially, if there is any non-ASCII symbol (more exactly, 8-bit symbol, the e-mail program may (or in some cases should?) send the message differently, even though it is a text-only message. The program would use so-called "MIME" format, where the message would appear as a "multi-part". And that is most likely treated by Doug's server software (mailman) as a message with an attachment. So, the message is not passed through.

[Geek_Language On]
When that happen, the headers of the message would have lines as these three:

MIME-Version: 1.0
Content-Type: multipart/mixed; BOUNDARY="518673661-1546572836-1455812812=:60197"
   ....

And then the body of the message would be starting with:

--518673661-1546572836-1455812812=:60197
Content-Type: text/plain; FORMAT=flowed; CHARSET=UTF-8
Content-Transfer-Encoding: 8BIT

And even though here, it is "Content-Type: text/plain", the line
"Content-Type: multipart/mixed;" in the headers.


For comparison, when this doesn't happen, the header lines look like this:
MIME-Version: 1.0
Content-Type: text/plain; FORMAT=flowed; CHARSET=US-ASCII

[Geek Language Off (mostly)]

What can cause this? That can happen if you are copying some text from the website that contains either some non-English symbols, or some Microsoftified symbols (e.g. "..." replaced with a single symbol).

That's why I asked Nicole about the mail program that she used.
Godfrey's response is consistent with that Apple Mail might be doing the same.

Godfrey DiGiorgi wrote:

Same as I use, Nicole. Be sure to set Mail to default to plain text only. I find that occasionally it switches to rich text on replies, so I always check the mode before sending.

So, I hope this information would be helpful.
If you have problems responding to or sending a particular message, check if all symbols are just plain ASCII symbols (as in 7-bit English letters).


Igor

PS. In my case, the program is alpine.


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