Tested with Roundup version 1.5.1 with config.ini settings:

[pgp]
enable = yes
encrypt = yes
require_incoming = encrypted


When requesting a password reset via the web interface, the
reset email is sent unencrypted.

So far I haven't tested with newer Roundup versions.

Hi Thomas:

In message <1598864970.91.0.430551620876.issue2551089@roundup.psfhosted.org>,
Thomas Arendsen Hein writes:
>When requesting a password reset via the web interface, the
>reset email is sent unencrypted.

The reset email is sent using mailer.py:Mailer::standard_message. This
method doesn't send encrypted emails. The bounce_message method in the
same class does support pgp encryption and may provide an outline of
how to implement encryption. Maybe changing the signature to include
crypt=False and implementing pgp encryption would work?

I assume your concern is that the reset email url is available in
plain text and could be used by a bad actor?

>So far I haven't tested with newer Roundup versions.

I did the analysis using 2.0.0 so password reset emails are still
unencrypted.

> I assume your concern is that the reset email url is available in
> plain text and could be used by a bad actor?

Yes, and the next mail has the password and is unencrypted.