This thread is about logging to mail servers using OLD, deprecated mail clients in retro machines. I’m afraid this will not be of use for Windows 10. You should create a new thread for your issue instead.

Update: I am still able to send and receive emails with Outlook 5.0 on Windows 3.11 guest VM, using stunnel on host machine.

I am looking for a way to make stunnel work with office365, I've recovered my old first Hotmail account but so far I can only receive, not send. I need to figure out why it is not sending. For Outlook 6.0+, stunnel is not required, because Windows 3.11 mail/web programs (IE5.01, OE 5.0) can only go up to SSL 3.0.

But seeing how roytam1 went as far as giving TLS 1.2 support to older Firefox for Windows 9x+, I tend to think why it would be difficult to do the same for any 16bit software... like... Netscape, the direct grandfather of Firefox?

EDIT: Seems that the problem with the SMTP on office365 (smtp.office365.com:587) has to do with the authentication. I can connect to the server, but I can not authenticate. Strange. I can retrieve my emails with pop3 though...

EDIT 2: It's definitely an authentication problem. Gmail accepts plain authentication when less secure apps is ON, but office365 does not have a such setting to "unlock" this.

EDIT 3: And office365 will never have it. Seems that since 2017 it has disabled plain authentication for it. I can receive emails, but not send. I still believe that it would send emails if I had the right PEM certificate for it. (Has to be DigiCert Cloud Services certificate). We will never know.

Anyway seems that I will be forced to stay on Gmail for legacy email services while I use a 2nd account for that with Less Secure Apps enabled. It's a safe decision.

Just came back to note that office365.com mail is working with the stunnel solution I posted on page 5.

I got FLmail working with Gmail on my Versa M/75 in freedos by disabling the expanded security on my Gmail acct. Thats not an optimal or favored option...but it worked.

Not optimal yes, but works. I'd recommend to use a 2nd gmail account for that, if you're using a main account. You could forward the emails from main to the 2nd so you can read them on your Versa and still be safe.

I was wondering, avoiding all these steps and making life easier, is there no free email service, which can be used quietly with Outlook 6?
Or with Outlook 97? I'd love to use this!

Did you read the thread?
Your best bet is to use stunnel. Your client would point to yourself at port 25 and stunnel would talk to the distant end at whatever port. Of course for this to work stunnel on whatever OS you are using would need to be updated enough to talk to the distant end.
See http://wp.xin.at/archives/tag/windows-2000

Yes, but I don't have a raspberry or a pc with linux.
I took a look at the guide you sent me, interesting, but complicated for me. At this point I am wondering if there is a lightweight email program that can now be used with windows 2000

You can try Thunderbird 12.0.1, no guarantees if it can connect via SSL/TLS, if not likely the ciphers are out of date and could possibly be updated like they have for retrozilla, new moon and k-melon.

You don't need another PC to use stunnel.
If you aren't against using the BlackWingcat Kernel then you can likely use newer versions of email clients.

DosFreak wrote on 2022-10-20, 16:59:

You can try Thunderbird 12.0.1, no guarantees if it can connect via SSL/TLS, if not likely the ciphers are out of date and could possibly be updated like they have for retrozilla, new moon and k-melon.

You don't need another PC to use stunnel.
If you aren't against using the BlackWingcat Kernel then you can likely use newer versions of email clients.

I found Pegasus Mail, but I don't know if it's okay.