pfSense

2.1.x config snippet:

<smtp>
    <ipaddress>mail.example.com<ipaddress>
    <port/>
    <ssl>unchecked</ssl>
    <tls>checked</tls>
    <notifyemailaddress>admin@example.com</notifyemailaddress>
    <username>admin@example.com</username>
    <password>asdfghjkl</password>
    <fromaddress>admin@example.com</fromaddress>
</smtp>

Results exactly in the same config with 2.2-RC after upgrade.

Looking at mail server logs, this does not attempt to use STARTTLS or anything, spews some garbage, connection gets terminated by mailserver due to too many errors and nothing gets sent. At this stage, the GUI looks like this:

After I uncheck Enable SMTP over SSL/TLS and click save, the following is saved:

<smtp>
    <ipaddress>mail.example.com</ipaddress>
    <port/>
    <tls/>
    <notifyemailaddress>admin@example.com</notifyemailaddress>
    <username>admin@example.com</username>
    <password>asdfghjkl</password>
    <fromaddress>admin@example.com</fromaddress>
</smtp>

STARTTLS is sent at the start of the sessions and everything works again.