[stunnel-users] Need help connecting Eudora to mail servers

[Phil Smith III]

+the list again because there are sure folks who know a lot more about stunnel than I do. I know email/SMTP/POP very well, stunnel not as much! There's nothing sensitive in the .conf file, so.


Set a full path for the log:

output = C:\temp\stunnel-log.txt

...or equivalent.

Simplify. Comment out all but Yahoo until you get that working. And did you try it without the extra records?

I don't see how you can have multiple hosts using the same incoming port: how would it know which one it's going to? And that's likely a big part of your problem here.

Consider the flow: A connection comes in to stunnel on port 110. How would it know "Oh, this connection should get routed to Yahoo" vs. "this connection should get routed to gmail"? It won't.

You CAN set the POP port per connection in Eudora:
https://www.digiportal.com/support/58-help-with-manual-configuration/264--setting-your-pop-port-manually-in-eudora-.html

But, again, I'd simplify. Get it working with each service, one at a time, using port 110. Then add them back in, one at a time, changing the port for each per the link above. Remember to close Eudora before tinkering with the .ini (and save a copy of the .ini first, just in case)!

So you'll wind up with something like (NOT right, surely, but illustrative. Look for records starting #! for inline commentary. I changed your comment string to # from ; just because otherwise I'll get it wrong :)

Again, I removed all the extra records you had. Those might be needed, but I'd start without them. And (one more time) start with JUST one service.

--
#***************************************************************
#  STUNNEL LOG
#! Fix path below to something that will work for you 
#!  (if you have c:\temp it's fine)
output = c:\temp\stunnel.log
#
#*****************************************************************


#*******************************************************
#Yahoo connection
#*******************************************************
[yahoo-pop3]
client = yes
#! Note POP port changed to 1110 -- need to change in
#!  Eudora for this connection
accept = 127.0.0.1:1110
connect = pop.mail.yahoo.com:995

[yahoo-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.mail.yahoo.com:465
#
#*******************************************************
#Bigpond connection
#*****************************************************
[bigpond-pop3]
client = yes
#! Note POP port changed to 2110 -- need to change in
#!  Eudora for this connection
accept = 127.0.0.1:2110
connect = pop.bigpond.com:995

[bigpond-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.bigpond.com:465

#*************************************
#Gmail connection
#********************************************

[gmail-pop3]
client = yes
#! Note POP port changed to 2110 -- need to change in
#!  Eudora for this connection
accept = 127.0.0.1:3110
connect = pop.gmail.com:995

[gmail-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
--
-----Original Message-----
From: stunnel-users [mailto:stunnel-users-bounces at stunnel.org] On Behalf Of Joe Slaven
Sent: Wednesday, May 20, 2020 7:20 AM
To: stunnel-users at stunnel.org
Subject: [stunnel-users] Need help connecting Eudora to mail servers


Below are the contents of my config file:

Question 1.  Is  the output statement correct?  I  cannot find the log file. I  expected it to be in the stunnel folder in the Program (x86) folders
Question 2.  Is it permissable to install code for all three email servers, using the same ports  and settings in Eudora?
Question 3. All three have error messages in Eudora ie none of them work via stunnel.  Can anyone please show me where I  am going wrong? I  have listed the error message for Gmail below. There is no log file that I  can find.

Bigpond error message:
There has been an error transferring your mail
POP server [JoeS4814 at 127.0.0.1 ] said
ERR[AUTH] Username and Password not accepted

thanks for helping out,
Joe


;***************************************************************
;  STUNNEL LOG
output = stunnel.log
;
;*****************************************************************


;*******************************************************
;Yahoo connection
;*******************************************************
[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
;
;*******************************************************
;Bigpond connection
;*****************************************************
[bigpond-pop3]
client = yes
accept = 127.0.0.1:110
connect = pop.bigpond.com:995
verify = 2
CAfile = ca-certs.pem
checkHost = pop.bigpond.com
OCSPaia = yes

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

;*************************************
;Gmail connection
;********************************************

[gmail-pop3]
client = yes
accept = 127.0.0.1:110
connect = pop.gmail.com:995
verifyChain = yes
CAfile = ca-certs.pem
checkHost = pop.gmail.com
OCSPaia = yes

[gmail-smtp]
client = yes
accept = 127.0.0.1:25
connect = smtp.gmail.com:465
verifyChain = yes
CAfile = ca-certs.pem
checkHost = smtp.gmail.com
OCSPaia = yes
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