Thanks Miguel,

Your suggestion is great when having self signed certificates.

It turned out my situation was not because Apple devices were having
problems with TLSv1 like I initially thought.

A backup server had a technical failure and it had rebooted and then
automatically started a backup version of the (virtual) mail server.
So the "real" and "backup" server were both online having the same IP.

This apparently caused some confusion with the clients :) Took one
full day to figure this out white trying all kinds of myriad fixes.

I take this as a sign to finally start the migration to newer OS on
this server. Now I would need to decide if I should go with COS7 or
COS8...

Best,
Peter




On Mon, Aug 24, 2020 at 12:20 AM Miguel Angel Amable Ventura
<mvent...@compu-tecnia.com> wrote:
>
> Hi Peter,
>
> You need to tell your users to delete the pop/imap account completely
> (not editing it) and register again just from the very beginning and
> they need to be connected to the wifi so the trust certificate shows the
> "trust option" to check it (in details) and finish their register. That
> can happen when you change the actual certificate or it has expired, I
> use my self-signed-certificates and set the expiry time at 10 years
> forward. When signing you need to use the option -extensions v3_ca as
> follows:
>
> openssl req -x509 -nodes -days 4825 -newkey rsa:2048 -keyout server1.key
> -out server1.crt -extensions v3_ca
> cat server.crt server.key > servercert.pem
> cp servercert.pem /var/qmail/control/servercert.pem
> chmod 640 /var/qmail/control/servercert.pem
> chown root.vchkpw /var/qmail/control/servercert.pem
> openssl pkcs12 -export -out mail4.pfx -inkey server.key -in server.crt
>
> When you use that option (extensions) apple/microsoft products can give
> you an option to trust your certificate.
>
> Greetings!
>
>
> El 22/08/2020 a las 04:28 a. m., Peter Peltonen escribió:
> > I have an old COS5 qmailtoaster
> >
> > Since yesterday Apple devices using its Mail program have been
> > receiving messages about certificate being not valid. Its a wildcard
> > certificate that is being used elsewhere as well so it should be valid
> > (it has not been expired).
> >
> > All other devices / clients seem to work also.
> >
> > As COS5 openssl uses TLSv1 I started wondering if Apple has deprecated
> > it from its Mail clients...?
> >
> > I do have this fix enabled:
> > https://www.qmailtoaster.org/newopensslcnt50.html
> >
> > But I assume it does not affect Dovecot which is still using the old
> > OpenSSL, right?
> >
> > So my only option really is to upgrade... Should have done it ages ago
> > of course. Just wondering if some quick fix came to somebody's mind so
> > I could buy some time to do the upgrade with a little more
> > preparation?
> >
> > Best,
> > Peter
> >
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