On Tue, May 16, 2023 at 7:07 AM Tim Moody <t...@timmoody.com> wrote:
>
> Thanks. That got me closer. I was not using ssl. When I took your code and 
> tried to connect to localhost I got
>
> STARTTLS extension not supported by server

*nod* The local relay is bound to localhost, so I guess we never
worried about adding transport security. I would hope that things
would work by just leaving out the starttls() call and related ssl
setup. I have not tested that myself at this point however.

> when I connected to mx-out03.wmcloud.org I got
>
> (220, b'TLS go ahead')
>
> But when I then do
>
>  server.sendmail("nore...@wikimedia.org", "t...@tim.com",
> ... """Subject: smtplib example from Cloud VPS
> ...   ...
> ...   ... Hello world.
> ...   ... ---
> ...   ... Bryan""")
>
> I get SSL: WRONG_VERSION_NUMBER

I saw that in one of my own tests as well. I don't have a good
explanation of what triggered it.

> In the console /usr/sbin/sendmail -v t...@tim.com <email.txt
>
> works just fine, so maybe I should just use subproc.

If shelling out to the sendmail client works for your use case, go for
it! Simpler is nicer in most things. :)

Bryan
-- 
Bryan Davis              Technical Engagement      Wikimedia Foundation
Principal Software Engineer                               Boise, ID USA
[[m:User:BDavis_(WMF)]]                                      irc: bd808
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