Logging into Gmail with old mail clients

[keenmaster486]

I already turned on the less secure apps thing - without it, I can't log in with Outlook Express 6.0 or 5.5. I'm trying to get Outlook Express 5.0 to work, due to it being the only promising mail client that runs on Windows 3.1.

[bfcastello]

The problem is with older versions of SSL being deprecated. Disabling OAuth/2FA won't address this.

I thought the same. I spent a few hours researching about how to make my raspberry pi work as a gateway for this. I saw your links, but I couldn't understand a word really - beginner here - and I needed to know if after getting these things from the links (fetchmail, getmail, ssmtp...) working, all I needed was just the ip of my rPi3 instead of the smtp/pop3 address?

The only thing that I have running on my rPi3 is a script that acts as some kind of "fake isp". This way, I can get WFWG3.11 to connect to the internet through Trumpet, and is running from my iPad Pro on iDOS2 (a port of DosBox for iOS). Quite a lot of work, really.

[bfcastello]

https://security.stackexchange.com/ques ... es-in-2015

While on the subject, this post explains a little about why https does not work on IE5

[NoNameNeeded]

Forget about OE5.
I tried to get this to work on Win95 and somehow it was never really able to receive or transmit e-mails, even though the settings were apparently correct.
I was however able to receive e-mails by messing with the settings and then (to send emails) I changed the settings again and it would send the e-mails.
But no settings would be "good enough" to both send and receive e-mails.

On Win95 it's no problem, you can use Thunderbird instead but on Win 3.1 you're out of luck, I'm afraid.

[bfcastello]

Forget about OE5.
I tried to get this to work on Win95 and somehow it was never really able to receive or transmit e-mails, even though the settings were apparently correct.
I was however able to receive e-mails by messing with the settings and then (to send emails) I changed the settings again and it would send the e-mails.
But no settings would be "good enough" to both send and receive e-mails.

On Win95 it's no problem, you can use Thunderbird instead but on Win 3.1 you're out of luck, I'm afraid.

Now that you mentioned Thunderbird...

Outlook was not my first choice 25 years ago. I remember flashes of me using Eudora. Can’t remember which version.

[gdjacobs]

The problem is with older versions of SSL being deprecated. Disabling OAuth/2FA won't address this.

I thought the same. I spent a few hours researching about how to make my raspberry pi work as a gateway for this. I saw your links, but I couldn't understand a word really - beginner here - and I needed to know if after getting these things from the links (fetchmail, getmail, ssmtp...) working, all I needed was just the ip of my rPi3 instead of the smtp/pop3 address?

The only thing that I have running on my rPi3 is a script that acts as some kind of "fake isp". This way, I can get WFWG3.11 to connect to the internet through Trumpet, and is running from my iPad Pro on iDOS2 (a port of DosBox for iOS). Quite a lot of work, really.

Yes, that's essentially the idea. You need something that can do SMTP locally, POP3 locally, POP3 retrieval over TLS remotely, and SMTP delivery over TLS. Because the local connection would be unencrypted, pretty much any mail client will be compatible.

Be aware, though, that configuring something like Postfix will be fairly weird at first.

[bfcastello]

Looking in the settings, Windows for Workgroups 3.11 with Internet Explorer 5 + Outlook Express 5 supports both SSL v2 and SSL v3. Studying the history of SSL, I don’t think the SSL 3 standard was changed since 1996 when it was promulgated. I see the corresponding option in XP for TLS 1.0 but that box is unchecked by default and it makes no difference; Outlook Express both 5 and 6 don’t even support TLS.

https://en.m.wikipedia.org/wiki/Transpo ... r_Security

This doesnt really answer anything about email clients for you, but does for web browsers. For example, only IE 6 and Opera 5.x supports TLS 1.0. We are really out of luck and need a web proxy rendering script to view these HTTPS sites on our older browsers. As for email clients, we need all the work that was said above to set up a gateway for unencrypted emails.

I am wondering if I might have a better luck with Windows NT 3.51. Granted, its not W3.x nor WFWG3.x, would be a “cheat” into my objective of creating something close to what I had 25 years ago, but it still retains the old GUI (Program Manager) look and feel.

[DosFreak]

For secure connections you're kind of SOL but you can try the following:

For 3.51 Seamonkey 1.1.20 will work just make sure you read the following:
http://toastytech.com/files/95browsing.html
http://toastytech.com/guis/misc4.html

It looks like tls 1.0/1.1 might be deprecated for email on some servers like they are for the web so you can try roytam1 retrozilla which works on 3.51 and supports TLS 1.2 https://dirteam.com/dave/2018/01/10/off ... s-tls-1-2/

browser-only retrozilla: http://o.rthost.cf/gpc/files1.rt/rzbrow ... 20180504.7
for suite: http://o.rthost.cf/gpc/files1.rt/rz-sui ... 0180708.7z

I haven't tried the mail client though only the browser which works for tls 1.2 sites....when the content renders correctly of course. heh.

Really though a proxy is the easiest way around this since no one seems interested in 3.x (And who could blame them)

Another option would be to use Links 2.18 browser for DOS, log into the web client and check email or port Links 2.18 to 3.x. (I'm assuming it won't work correctly in 3.x command prompt but you never know)

Have you tried Opera 3.62 or Netscape Communicator 4.08 mail clients or browsers?

[keenmaster486]

Yes, I've tried various browsers to load gmail in browser, and none of the Windows 3.1 browsers work properly for that. Links in DOS works beautifully but this is about getting email in 3.1.

For that matter, none of the Windows 3.1 browsers are usable at all on the modern web. They either crash incessantly or don't even have SSL3 security, or both. None of them have TLS. Links is far better; it seems to connect to everything and do its best to render what it can. Gmail renders just fine.

Creating a proxy server for the web and "in-between" mail server is, of course, the best long-term solution. Eventually maybe we will have something that runs on a Raspberry Pi and performs a "retrofication" operation on all the web traffic, turning everything into older standards, maybe also letting you select the standard you want. But I'm getting ahead of myself here.

I think the specific question I'm trying to answer is this: Both Outlook Express 5.0 and 5.5 support maximum SSLv3 security. And yet 5.5 works while 5.0 fails to establish a secure connection. Why?

[DosFreak]

Setup a hub or switch with port mirroring and load wireshark up to see what the traffic is doing. Could be a bug in the program or server side or both.

Did you try the mail clients in Opera and Netscape?

[bfcastello]

I tried both opera and netscape on WFWG3.11

Imagine my surprise when Opera rendered perfectly the google search page. But then it all began. Opera crashes A LOT and renders the whole system unusable when it crashes. Netscape was almost useless and slow.

[DosFreak]

It looks like Retrozilla TLS 1.2 is crashes on start for some reason so will need to ask roytam1 about that. Retrozilla 2.1 works fine
viewtopic.php?f=24&t=12102&p=728682#p728682

Can't find retrozilla 2.1 suite equivalent whereas there is one for Retrozilla TLS 1.2 with the mail client.

To access TLS 1.2 sites with Retrozilla 2.1 on NT 3.51 you'll need to use a proxy. I verified this as working today by logging into the basic html version of gmail.

You can try these proxy sites if you don't want to setup your own proxy, they will load but if you're browsing doesn't support newer HTML and Javascript then those sites will be broken:
1) http://proxycrime.com
2) http://fastusaproxy.com
3) http://trubadix.myds.me/ppp
4) http://usafastproxy.info
5) http://prositeproxi.com
6) http://frenchproxy.info
7) http://ghostme.tech
http://freshwebproxy.tech

[bfcastello]

It looks like Retrozilla TLS 1.2 is crashes on start for some reason. Retrozilla 2.1 works fine
viewtopic.php?f=24&t=12102&p=728682#p728682

Can't find retrozilla 2.1 suite equivalent whereas there is one for Retrozilla TLS 1.2 with the mail client.

To access TLS 1.2 sites with Retrozilla 2.1 on NT 3.51 you'll need to use a proxy. I verified this as working today by logging into the basic html version of gmail.

I gave up on NT 3.51 since it can’t run on DosBox and iDOS 2. Almost thought about going to W95, but I was never a fan of this GUI. I guess that I will really have to set up my rPI3 to run some scripts in the middle.

[DosFreak]

There is a script on virtuallyfun to convert webpages to gifs. Looked pretty neat but haven't tried it myself.

https://virtuallyfun.com/wordpress/2014 ... xy-update/
https://github.com/tenox7/wrp

[bfcastello]

https://68kmla.org/forums/index.php?/to ... lder-macs/

We are not alone. The friends using old macs and/or emulating old macs are on the same boat.

[bfcastello]

https://github.com/justinschw/legacyweb

I tested this on my rPi3. Downloaded, installed, configured. Then proceed to set up Outlook Express on my WFWG 3.11. To my surprise, it did connect, but google (I tried gmail first) blocked it, it keeps asking me for my authentication. Then I went back to the rPi3 and tried to configure for outlook. Same result. I am yet to try Yahoo! now.

[keenmaster486]

To my surprise, it did connect, but google (I tried gmail first) blocked it, it keeps asking me for my authentication.

Did you turn on the "allow legacy apps" thing on your Google account?

[bfcastello]

To my surprise, it did connect, but google (I tried gmail first) blocked it, it keeps asking me for my authentication.

Did you turn on the "allow legacy apps" thing on your Google account?

Yes, I did. This is exactly what made me scratch my head.

[bfcastello]

That’s it, I tried three different accounts: yahoo, outlook and gmail. They all produced the same error, password was rejected when I try to login on POP3.

[yawetaG]

I gave up on NT 3.51 since it can’t run on DosBox and iDOS 2. Almost thought about going to W95, but I was never a fan of this GUI. I guess that I will really have to set up my rPI3 to run some scripts in the middle.

IIRC, you can switch Windows 95 to use the old Win3.x GUI...