Modern email and vintage clients

2023-08-04 18:10:00

I was trying to use my email server from my PowerMac G4 under MacOS9 but as usual with old systems the crypto stuff was blocking and I didn’t want to open my mail server to more attacks. After searching the web, asking on the fediverse didn’t find much but then eureka I remembered stunnel is a thing! I prompty installed it on a Pi I have, added a mail.conf in /etc/stunnel:

/etc/stunnel/mail.conf

[pop3]
client = yes
accept = 110
connect = my.mail.server:995

[imap]
client = yes
accept = 143
connect = my.mail.server:993

[smtp]
client = yes
protocol = smtp
accept = 25
verify = 2
CApath = /etc/ssl/certs/
connect = my.mail.server:587

Added some firewall rules, reloaded stunnel et voila I can now connect from my G4 using Outlook Express or Classilla! I use my Pi address as the email server and everything is tunneled to my real server with the proper encryption.

Note that my SMTP is configured with STARTTLS so you might have to tweak things to use TLS.