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sTunnel and Gmail on Mac Plus

WakelessFoil

Well-known member
So I just got stunnel working on my pi so I can now read my gmail on my Macintosh Plus using Eudora Lite 1.x!

There is one problem though, I cannot send emails because of what I believe to be a security problem. I am not sure what's wrong but I get this error message (see below) when the mac tries to send emails to stunnel. I think stunnel is expecting the messages to already be secured or it is expecting smtp authorization. I am not sure how to fix this as I have very little IT background, hopefully someone here smarter can help! Thanks.

PS: I also attached an image of my stunnel.conf file on the pi.IMG_5717.JPG

IMG_5715.JPG

 

WakelessFoil

Well-known member
Google made some changes to disable "less secure" applications recently, you might need to turn those back on (with the relevant caveats, of course): https://support.google.com/accounts/answer/6010255
I made sure to let gmail use less secure applications. I’m certain now that Eudora is not sending the smtp authorization that stunnel requires to send mail to gmail. I’m currently looking for a service/program that I can run on my raspberry pi that will add in the smtp credentials for stunnel as I believe I can’t do that within stunnel itself.

 

Nathan

Well-known member
What version of the OS are you running? Could you just use a more recent version of Eudora like Eudora 3.x?  

Might be some meaningful tidbits on this webpages:

https://www.fenestrated.net/mac/68kMail/  

https://lowendmac.com/misc/01/0716.html

https://www.jagshouse.com/mulberry.html

Looks like Mulberry Mail is one of the very few options you have for 68k mail clients with SMTP auth support:  

https://www.macintoshrepository.org/2681-mulberry-2-x-email-client-

^ looks to be downloadable here, though IDK what the feature set is without a license key..

http://bylenga.ddns.net/index.php?page=68KEmail.php

^ a little setup explanation

 
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Hopfenholz

Well-known member
It seems that Gmail ended SSLv3 support way back in 2016 and these old solutions (Baton, Mulberry) don't work for Gmail today. Shame. I'm still researching, if anyone has IMAP Gmail access working on a Classic Mac OS system I'd love to hear about it.

 

Hopfenholz

Well-known member
I've just got stunnel working on my Raspberry pi (rescued from the bottom of a drawer). Was pretty painless! Now to try and get a mail client working

 
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ArbysTPossum

Active member
Anyone know if this still works, or will work? I've tried it, but I think I'm doing something wrong. Trying to receive mail on a Gmail account so I can sync them all to my Palm Pilot.
 

ArbysTPossum

Active member
Update on this, I'm pretty sure I'm not doing anything wrong, but it's still not working. The routing is working because every time I change a port or to/from IP I get a different error, possibly the cert is wrong but I'm unsure. I've tried Gmail, Yahoo and ProtonMail, none of them like it.
 

VMSZealot

Well-known member
Instead of sTunnel, which I couldn't get to work either, what about this? https://github.com/PascalHarris/NetGateway

It's been a while since I last worked on it - and there were some things which didn't work right - but the instructions are there, and I was at least able to get it to go with Claris Emailer.

I'm open to bug reports (when I have time to look at them) and happy to accept any changes that anyone else proposes.
 

ArbysTPossum

Active member
I'll look into it this evening if I can find the time. Looking at the files/config, I think I know how it's supposed to be used, but I wouldn't turn my nose at any advice.
 

ArbysTPossum

Active member
I can't get it to make on a Raspberry Pi, but my 2013 MacBook Pro did it after installing some stuff. Not ideal, but I think I can make it work still.
 
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