As of about a month ago (
https://github.com/pfsense/pfsense/commit/1cddd59c4ed2341f87cf58d9b67d45c82ffd99d0)
StartTLS is an independant setting and should work no matter what port you
are using.
I do not know whether that code has made it to a release (can log in to
check from where I am now) and I don't know how much that changed the
behavior from before, but it is probably worth a look.

- Y


On Wed, Oct 16, 2013 at 5:53 PM, Andreas Meyer <[email protected]> wrote:

> Hello!
>
> Moshe Katz <[email protected]> wrote:
>
> > On Wed, Oct 16, 2013 at 5:41 PM, Andreas Meyer <[email protected]> wrote:
> >
> > > Hello all!
> > >
> > > php: /system_advanced_notifications.php: Could not send
> > >  the message to [email protected] -- Error: 530 5.7.0 Must issue a STARTTLS
> > > command first
> > >
> > > Is starttls possible with pfsense?
>
> > There is a checkbox on the "System" -> "Advanced" -> "Notifications" page
> > that says "Enable SSL/TLS Authentication".  Make sure that box is
> checked,
> > and it should work.
>
> Isn't that checkbox for port 465 only?
> php: /system_advanced_notifications.php: Could not send the message to
>  [email protected] -- Error: could not connect to the host "mail.anup.de": ??
>
> >
> > Moshe
>
>   Andreas
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>
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