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.

Hello all,

I would like to come back to NarakuITA comment as it will be most adequate for me as well allowing also the usage of even older dos mail programs:

Is anyone aware of mail providers allowing unencrypted smtp/pop3?

I couldn’t find any.

Thanks

Edit: I could also think of following internal router solution based on openwrt:

To set up a mail client and server on OpenWrt that retrieves encrypted emails from „your secure mail provider“ and provides them to your retro PC via unencrypted POP3/SMTP, follow these steps:

Step 1: Install Required Packages

First, ensure you have the necessary packages installed on OpenWrt:

1. Postfix: For sending emails.
2. Dovecot: For receiving emails.
3. fetchmail: To retrieve emails from „your secure mail provider“

Further update: Gmail no longer allows „less secure“ connects

Marco wrote on 2024-11-04, 12:52:

Further update: Gmail no longer allows „less secure“ connects

Yup they removed that a little while back, I only know because it nuked my access via an older version of Thunderbird I was using on my Win 10 PC, the version on my daily 11 PC updated fine so I just had to fix the account login settings.

For the curious I have Group Policy settings that lock the PC down so it cant update unless I let it, I do the same for most 3rd party apps too, got sick of updates breaking shit on me.

Works fine for Windows Update too .. never going to update to 24H2 and that Recall shit, it can stay off my PCs.

Further update... Microsoft Office365/Outlook no longer allows "less secure apps" too.

The workaround now is to use an email proxy python script. You'll need Python 3.x. I spent the day trying to figure out one by myself, but I ended up using a ready one from this github: https://github.com/simonrob/email-oauth2-proxy

Tested with OE 5.0 and 6.0 on Windows 95, 98, Me, XP and MacOS 9.2. Received emails ok, I haven't tested submitting them yet.

My previous workaround implied the use of an stunnel to downgrade the TLS protocol when less secure apps was allowed. Now I no longer need it, just the proxy script. The steps (as I remember, I spent a day trying to understand I still quite dont understand the complexities of it yet:

1. Clone the project
The usual git clone... y'all know how, right? Then get into the project and start configuring it. First you need the dependencies. Clone or download the GitHub repository, then:

1python -m pip install -r requirements-core.txt -r requirements-gui.txt

2. Configure emailproxy.config
Next, edit the sample emailproxy.config file to add configuration details for each email server and account that you want to use with the proxy. You need some credentials. You can remove details from the sample configuration file for services you don't use, or add additional ones for any other OAuth 2.0-authenticated IMAP/POP/SMTP servers you would like to use with the proxy. Initially I tried to configure an App ID on Azure so I could get a token for it to connect, but failed miserably. The other workaround was to use an App ID from an existing app: Mozilla Thunderbird. You can check it here: https://blog.thunderbird.net/2023/01/importan … terprise-users/ and here https://github.com/simonrob/email-oauth2-prox … ment-2424200404

The following emailproxy.config was set for me if I wanted to use my old hotmail account, for starters I'll use an example with 'username@hotmail.com':

1[IMAP-1993]
2server_address = outlook.office365.com
3server_port = 993
4local_address = 0.0.0.0
5
6[POP-2995]
7server_address = outlook.office365.com
8server_port = 995
9local_address = 0.0.0.0
10
11[SMTP-1587]
12server_address = smtp-mail.outlook.com
13server_port = 587
14server_starttls = True
15local_address = 0.0.0.0
16
17[username@hotmail.com]
18permission_url = https://login.microsoftonline.com/common/oauth2/v2.0/authorize
19token_url = https://login.microsoftonline.com/common/oauth2/v2.0/token
20oauth2_scope = https://outlook.office.com/IMAP.AccessAsUser.All https://outlook.office.com/POP.AccessAsUser.All https://outlook.office.com/SMTP.Send offline_access
21client_id = 9e5f94bc-e8a4-4e73-b8be-63364c29d753
22redirect_uri = https://localhost:7598
23
24[emailproxy]
25delete_account_token_on_password_error = True
26encrypt_client_secret_on_first_use = False
27use_login_password_as_client_credentials_secret = False
28allow_catch_all_accounts = False

Then you run the script for the first time:

1MacBruno-Pro:email-oauth2-proxy bruninho$ python3 emailproxy.py

You will run the GUI version of the app, but there will still be terminal output. The proxy will be listening, ports 1587 and 2995, respectively, for SMTP and POP3. There is also IMAP if you want. Now, lets say I started a VM on 86box with Windows 98 and configured Outlook Express 5.0 to use my email, password can be anything (i used 'oauth2') and the IP for POP3 and SMTP is the network IP for your host machine (for example, 192.168.1.47). You set the ports 1587 and 2995 for each service. (Nearly the same configuration I used for the stunnel script I shared years ago here in this topic on page 5). Once Outlook is set up, run it (check send and receive emails).

The Outlook will go to the proxy, the proxy will then - only on first run of it - ask you to authorize the app (in this case, Office365 will ask you to authorize Mozilla Thunderbird to access your email) . In my case I had to go to the menubar for the emailproxy app icon, select the external mode for authorization, and select the email account. This will fire a web browser with a page explaining how to get the token for future access. You authorize the app, the result URL will be a broken URL, but don't fret. Copy the URL and paste it on the window opened by emailproxy. It will save the token in your emailproxy.config. After that, your old Outlook will be able to access the email service and retrieve/send emails.

3. Set it as a background service
You can do it if you want, or just run the proxy whenever you want to. But I made a launchctl daemon agent for it, so I dont need to run it whenever I want to check emails in my VMs, it will be running on background, headless, no GUI. The command to run without a GUI is:

1MacBruno-Pro:email-oauth2-proxy bruninho$ python3 emailproxy.py --no-gui

Then with a background service just forget about it. The GUI version of the App has an menu option to set it to launch on windows/mac startup. I prefer to make my own launchctl to disable logging and other useless stuff.

Now I can check my emails from my old machines!

Happy emailing 😉

Although I couldn’t test it yet: thank you very much for the detailed solution description!!