Have you looked at the stunnel log?

FWIW, I use stunnel to cox.net with Eudora (well, my wife does--I get to make 
it work) and just have the protocol, accept, and
connect statements and it works. You might try commenting those out and see, 
but the log is probably more interesting.

-----Original Message-----
From: stunnel-users <[email protected]> On Behalf Of Joe Slaven
Sent: Tuesday, May 19, 2020 8:48 PM
To: [email protected]
Subject: [stunnel-users] Eudora -> Yahoo problems

Hello, new to stunnel, my first attempt is connecting Eudora to Yahoo Mail.

My Yahoo Mail password and username are not being recognised when it
is trying to access server 127.0.0.1

Can anyone suggest why this will not work?

regards,
Joe

********************************************************************************************************

ERROR MESSAGE
There has been an error transferring your mail.
POP Server [[email protected]] said ERR [AUTH] Username and
password not accepted


STUNNEL CONFIG FILE SETTINGS
[yahoo-pop3]
client = yes
accept = 127.0.0.1:110
connect = pop.mail.yahoo.com:995
verify = 2
CAfile = ca-certs.pem
checkHost = pop.mail.yahoo.com
OCSPaia = yes

[yahoo-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.mail.yahoo.com:465
verify = 2
CAfile = ca-certs.pem
checkHost = smtp.mail.yahoo.com
OCSPaia = yes

EUDORA SETTINGS
Checking Mail->Mail POP Server:  127.0.0.1
Sending Mail->SMTP Server: 127.0.0.1
Use submission port (587) is UNchecked
Secure Sockets when Sending or Receiving : Never
Default port settings :
        SMPT Port (25)
        POP Port  (110)

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