I have no idea. I assume upgrading transmission wouldn't ask me to keep an
older file here and I did not modify any of these files until I ran into
the issue. I did that test on a fresh install which rules out me messing up
the files :)
Also, I'm not sure how I missed your email about this, sorry about that.
I'm not sure if this bug is still present in the current stable version. I
found this ticket after looking to make a new one for transmission in
Debian 12.

On Wed, 13 Oct 2021 22:16:52 -0400 Sandro Tosi <mo...@debian.org> wrote:
> control: tags -1 +moreinfo
>
> > It seems that this bug is caused by this change in Transmission:
https://github.com/transmission/transmission/pull/795
> > After changing my
> > /etc/systemd/system/multi-user.target.wants/transmission-daemon.service
> > to read "NoNewPrivileges=false" instead of true and reloading the
> > service and daemon, I find that transmission is properly sending emails
> > again.
>
> this is weird: that PR is included in the 3.00 release provided in
> debian, and infact the file
> /lib/systemd/system/transmission-daemon.service includes the PR
> change; how did you get that outdated file in /etc/systemd/system/ ?
>
> --
> Sandro "morph" Tosi
> My website: http://sandrotosi.me/
> Me at Debian: http://wiki.debian.org/SandroTosi
> Twitter: https://twitter.com/sandrotosi
>
>

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