pfSense

I can confirm this bug on pfSense 2.1.5-RELEASE. This also happens if instead of "Enable STARTTLS" you are using "Enable SMTP over SSL/TLS".

To reproduce:
1) Configure SMTP E-Mail, mine looks like this
- Email server: smtp.gmail.com
- SMTP port: 465
- Secure SMTP Connection: click on Enable SMTP over SSL/TLS
- From email: my_email
- notification email: recipient_email
- notification email auth username: my_email
- notification email auth pass: my_email_password

2) After configuring all the aforementioned fields click on save

3) After webpage is reloaded click on Test SMTP

4) Webpage will be reloaded and everything will look normal, except that now Secure SMTP connection settings will look unticked (happens with both settings)

HOWEVER, if after step #4 you go to any other pfsense webpage (like clicking on System tunables), and then you click back to Notifications you will see that the "Secure SMTP connection" setting is still saved.

This means that clicking on Test SMTP is not erasing your configured "Secure SMTP Connection" settings. It means that you click on the test button the website that gets generated as a response to that click button is being generated incorrectly, providing you false representation of your settings, which leaves which the impression that the test button is messing with your settings.

Hope this helps a little.

I can confirm this bug on pfSense 2.1.5-RELEASE. This also happens if instead of "Enable STARTTLS" you are using "Enable SMTP over SSL/TLS".

To reproduce:
1) Configure SMTP E-Mail, mine looks like this
- Email server: smtp.gmail.com
- SMTP port: 465
- Secure SMTP Connection: click on Enable SMTP over SSL/TLS
- From email: my_email
- notification email: recipient_email
- notification email auth username: my_email
- notification email auth pass: my_email_password

2) After configuring all the aforementioned fields click on save

3) After webpage is reloaded click on Test SMTP

4) Webpage will be reloaded and everything will look normal, except that now Secure SMTP connection settings will look unticked (happens with both settings)

HOWEVER, if after step 4 you go to any other pfsense webpage (like clicking on System tunables), and then you click back to Notifications you will see that the "Secure SMTP connection" setting is still saved.

This means that clicking on Test SMTP is not erasing your configuration. It means that the website that is generated after you click on the test button displays incorrect information, not what your settings actually are. This leads you into the false belief that clicking the test button has altered your settings, which is clearly not the case.

Hope this helps a little.

This is fixed in 2.1 branch by https://github.com/pfsense/pfsense/pull/1308
Then I saw that it got re-engineered in master 2.2 and looks like it will work OK there already. But I suspect that settings of the 2 checkboxes may not upgrade cleanly from 2.1.n to 2.2 - see my comments in the pull request.

The pull request you mention indeed fixes the problem for me on 2.1. Thank you.