SMTP configuration incorrect in installer - with fix

[chrisale]

Steps to reproduce the problem

Case 1) In the script:

1. Follow steps on joinmastodon.org to install mastodon and prerequisites from source
2. run RAILS_ENV=production bundle exec rake mastodon:setup
3. attempt to configure with any SSL related authentication setting

Case 2) In a running mastodon instance have in the .env.production file the standard settings using port 465 / SSL:

SMTP_SERVER=mymailserver
SMTP_PORT=465
SMTP_LOGIN=myloginemail
SMTP_PASSWORD=mypassword
SMTP_AUTH_METHOD=plain
SMTP_OPENSSL_VERIFY_MODE=client_once
SMTP_ENABLE_STARTTLS=always
SMTP_FROM_ADDRESS=notifications@emailaddress

Expected behaviour

An email should be generated and successfully sent

Actual behaviour

The commands timeout and produces: "Net::ReadTimeout: "Net::ReadTimeout with #TCPSocket:(closed)" in script output and syslog

Detailed description

To resolve this problem we consulted this discourse link:
https://discourse.joinmastodon.org/t/new-mailserver-no-mails/3420

The problem appears to be in the SSL settings. SMTP_AUTH_METHOD, SMTP_OPENSSL_VERIFY_MODE and SMTP_ENABLE_STARTTLS are commented out and SMTP_TLS=true must be added.

My successful settings were:

SMTP_SERVER=mymailserver
SMTP_PORT=465
SMTP_LOGIN=myloginemail
SMTP_PASSWORD=mypassword
#SMTP_AUTH_METHOD=plain
#SMTP_OPENSSL_VERIFY_MODE=client_once
#SMTP_ENABLE_STARTTLS=always
SMTP_TLS=true
SMTP_FROM_ADDRESS=notifications@emailaddress

Related Mastodon Thread:
https://mstdn.ca/@chrisale/109725219048851990

Specifications

Debian 11
Mastodon | 4.0.2
Ruby | 3.0.4p208
PostgreSQL | 15.1
Redis | 6.0.16
OpenSSL 1.1.1

[smiba]

Could be a misconfiguration from your side, TLS and STARTTLS are not the same. Could you try this with SMTP_ENABLE_STARTTLS set to auto or never?

I do agree that it would make sense to also include the option for TLS (and not just STARTTLS settings) in the setup configuration if this is not fixed by using the following settings (could you test them out for us and let me know?)

SMTP_SERVER=mymailserver
SMTP_PORT=465
SMTP_LOGIN=myloginemail
SMTP_PASSWORD=mypassword
SMTP_AUTH_METHOD=plain
SMTP_OPENSSL_VERIFY_MODE=client_once
SMTP_ENABLE_STARTTLS=auto
SMTP_FROM_ADDRESS=notifications@emailaddress

(If it doesn't work, please try "SMTP_ENABLE_STARTTLS=never")

[chrisale]

I can confirm I have tried both those configurations in both the setup test script and the working server file and neither send successfully. Judging by inspecting the tcpdump, they do seem to negotiate a connection but they time out while trying to send an email.

In case it is helpful I have attached some of the output from openssl when connecting to and sending email through my smtp server manually. It works without any issue.