sTunnel and Gmail on Mac Plus

[WakelessFoil]

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.

 

[cheesestraws]

it is expecting smtp authorization

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

 

[WakelessFoil]

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.

 

[PowerPup]

You might be able to utilize Baton Mail on the Mac Plus to add SMTP authentication: http://web.archive.org/web/20060615060729/http://www.mythtech.net/baton.html

 

[Nathan]

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

 

[Hopfenholz]

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]

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

 

[ArbysTPossum]

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]

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]

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]

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]

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.

 

[applesos]

If you are willing to do sysadmin work and/or hate yourself enough you could always set up an SMTP relay on the Pi- it's Linux so you could install any mailserver software on there. There's plenty of people documenting ways to achieve this online and it would allow you to make sure the traffic flowing over the web is up to snuff for modern email cryptography standards. I'll just warn you that this sort of thing usually puts people on a road that ends with "making your own enterprise software for weird edge cases only you have"

 

[ArbysTPossum]

SMTP relay? I'll have to look into that. I miss the days where I would/could read and answer Emails on my Palmtop, then sync it later. No modern Email client has the ability to talk to a Palmtop, so it'll have to be an older machine, with an unsupported Email client. I just want it to work. :[

 

[luRaichu]

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

They don't even let you change this setting on newer Google accounts!

 

[NJRoadfan]

Google is completely removing the "less secure" apps and app-specific password options in the near future. Any solution now needs to use OAuth2 based authentication.

 

[ArbysTPossum]

For a hot second, I could get into a Gmail account, but that hasn't been an option for a good while. I've tried a bunch of other Email providers too, and older Email programs can't get into those either. Even if there was a less secure provider, I could just forward things to that and get them to my Palm device.

 

[Hopfenholz]

I would love to access email on a classic device but it seems impossible now even with a proxy device like a pi running stunnel

 

[applesos]

Yeah- at this point I think the only realistic way to do this would be with a paid email provider, an email relay server on your LAN, and maybe some scripting. I'm an IT admin and have functionally done similar things for clients who have scripts that send email alerts or on-prem mail solutions that they've integrated to cloud providers. Gmail supports similar setups, but again through workplace - see here. It looks like doing this for free is no longer feasible. https://support.google.com/a/answer/2956491?hl=en