Ignoring Gmail Certificate Changes in Eudora with Stunnel

Ignoring Frequent Gmail Certificate Changes by Getting Comcast, Godaddy, Eudora, Stunnel, and Gmail to Work Together in Windows 7

My email is now working without interruptions caused by Gmail's frequent certificate changes. I'd read that using Stunnel is a way to avoid the certificate update process. The process of making Stunnel work for me was frustrating for the people answering my questions as well as for me. Maybe this record will help someone else have an easier time of it as well as remind me how to fix it if/when I break it.

I'm posting these particular settings because my primary email requires that I use port 80 for SMTP. After trying several methods to circumvent that setting without success, it remains a requirement in this case.

After installing Stunnel as a service and leaving its configuration file unedited, I set up my Gmail personalities in Eudora by first setting the Properties for each personality to:

Generic Properties tab:

•     SMTP Server: 127.0.0.1

•     Use Submission Port: UNchecked

•     Secure Sockets when Sending: Never

Incoming Mail tab:

•     Secure Sockets when Receiving: Never

Then I closed/quit/exited Eudora, found Eudora.ini, made a backup copy, and used Notepad to open the original Eudora.ini file.

Each non-dominant persona has a section in Eudora.ini that starts out something like this where "gmailuser" and the domain varies:
---------------------------------------------
[Persona-gmailuser@gmail]
SavePasswordText=randomstuffencodingapassword==
POPAccount=gmailuser@gmail.com@127.0.0.1
RealName=Michal
ReturnAddress=gmailuser@gmail.com
DomainQualifier=
SMTPServer=127.0.0.1
---------------------------------------------
The important line is that bottom one, and it could be somewhere else in the settings for this persona or it could be missing (one of mine was despite being specified in Properties). For each gmail persona, I added SMTPPort=25 immediately after the SMTPSERVER line like this:
---------------------------------------------
SMTPServer=127.0.0.1
SMTPPort=25
---------------------------------------------
I repeated this edit for each Gmail persona, adding both lines when the SMTPServer line was missing. Then I saved Eudora.ini and closed Notepad.

After running Eudora again, I sent many test messages. I set up a group in the address book called All Personalities to simplify the addressing. I sent messages from each email address (Personality) to All Personalities, giving each subject line a unique number, and checked mail several times, watching for Task Errors, and confirming the messages all arrived. Several times. And then again. It all seems to be working correctly now.

Kudos to Jack Jackson and Katrina Knight at Eudora-Win List Server for explanations and answering my questions.