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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.thumb.JPG.9059347efe0742664ebb062a5312140d.JPG


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9 hours ago, cheesestraws said:

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.

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  • 1 month later...

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:





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



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



^ a little setup explanation

Edited by Nathan
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  • 8 months later...

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.

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  • 2 months later...

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