October: Auto switch SMTP port when changing protocol in the mail settings

[ayumi-cloud]

Want to confirm if this is a bug or not?

When I set the following:

SMTP address: secure.example.com
SMTP port: 465
SMTP encryption protocol: TLS
SMTP authorizaqtion required: ticked

I get a 504 connection error message when sending a test email.

SMTP address: secure.example.com
SMTP port: 465
SMTP encryption protocol: SSL
SMTP authorizaqtion required: ticked

Gets sent straight away when sending a test email.

Makes no sense as SSL is the older version and TLS is the upgraded version and my test server fully supports both.

I know many people have said SMTP doesn't work correctly in October for a while. I just wonder if this is the reason why?

Would be nice if someone else could confirm this.

[LukeTowers]

@w20k @bennothommo @mjauvin Could someone test this? @ayumi-cloud SMTP issues are typically issues with mail servers / configuration, and although lots of people may report issues related to SMTP that doesn't mean they're all having the same issue.

[mjauvin]

As far as I know, port 465 is implicit SSL and port 587 is explicit TLS.

So at first glance, I would think this is expected behavior.

[bennothommo]

@ayumi-cloud @LukeTowers As far as I know, in reference to Exim which powers half of the MTAs on the web, @mjauvin is correct - 465 is generally setup only for SSL connections, and 587 is generally setup only for TLS connections. (with 25 and 2525 being other common ports, but not recommended for use anymore). I use 465 all the time with our client websites (running on shudder cPanel servers), so I know it works.

[Eoler]

As far as I know, port 465 is implicit SSL and port 587 is explicit TLS.

Yeah, that's how it is configured on both Exim/cPanel and Postfix/KeyHelp servers.

[ayumi-cloud]

@LukeTowers @mjauvin @bennothommo @Eoler

Cool, thanks for the info.

• port 465 is for SSL connections.

• port 587 is for TLS connections.

• port 25 is for standard connections (many Internet service providers however block port 25).

• port 2525 allows insecure connections.

Going to close this unless, you want me to create a hint field in the Settings > Mail configuration page, with the info I summarized above.

[Samuell1]

That will be cool and maybe say that 25 port isnt recommended to use because it can work but it can be limited like AWS does limit it.

[bennothommo]

@ayumi-cloud Instead of the hint, I would instead have it so that when the "SMTP encryption protocol" value is changed, it replaces the SMTP port value to the default port for that protocol, as it's very unlikely that people are using non-standard ports for email - for example, if they switch it to SSL, it should change the port to 465, and for TLS, 587. I've seen lots of mail software and services do the same, so I would imagine people are used to it doing that now.

[mjauvin]

I agree, it is expected behavior nowadays.

On Sun, Nov 10, 2019 at 10:27 AM Ben Thomson [e-mail]
wrote:

@ayumi-cloud https://github.com/ayumi-cloud Instead of the hint, I
would instead have it so that when the "SMTP encryption protocol" value is
changed, it replaces the SMTP port value to the default port for that
protocol, as it's very unlikely that people are using non-standard ports
for email - for example, if they switch it to SSL, it should change the
port to 465, and for TLS, 587. I've seen lots of mail software and services
do the same, so I would imagine people are used to it doing that now.

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[ayumi-cloud]

@bennothommo sounds good, I will leave it with you to create the automatic port selection, based off the encryption settings.

Thanks to everyone's feedback. 👍

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