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Logging into Gmail with old mail clients

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Reply 80 of 109, by Bruninho

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keenmaster486 wrote:

What I would like to have is an email server running on a Raspberry Pi that I can log into with legacy clients, which then forwards everything transparently to the Gmail servers.

That would be the best option. But setting up an email server on a rPi3 requires some knowledge (which I don't have actually) - especially in what concerns about security.

I had one of my rPi3 hacked recently, I had to wipe it out and reinstall everything as a fresh install. The rPi3 must be really secure before any attempt to build an email server.

I'll try again to set up the IMAP folders on my OE versions (W98 and W2000) later, hopefully I can get the folders/labels to sync better. As for W3.x, I have no idea.

EDIT: According to my research, OE 5.0 ~ 6.0 will only "speak" TLS 1.0. To support TLS 1.1 and above, needs to be replaced by newer clients. So, it's the final straw for OE in W3.x and maybe also any OE on any Windows below Vista - when it was replaced by, if my memory serves right, Windows Mail.

Last edited by Bruninho on 2019-07-16, 03:04. Edited 2 times in total.

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Reply 81 of 109, by Bruninho

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Speaking of protocols, since SSLv3 is deprecated (because POODLE attack), how one can turn off older protocols (SSL3.0, TLS1.0...) for the following Ones and browsers?

Opera, Edge*, Safari, Firefox, Chrome

Win98, Win2000, Win10, macOS and iOS ? (and maybe Raspbian and Ubuntu Linux)?

I think the subject deserves its own topic - seems to be very useful information for everyone, after all its about the security of our data that we are talking about. I think TLS 1.1 and 1.2 are the most current ones.

https://thehackernews.com/2018/10/web-browser … upport.html?m=1

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Reply 82 of 109, by Bruninho

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keenmaster486 wrote:

What I would like to have is an email server running on a Raspberry Pi that I can log into with legacy clients, which then forwards everything transparently to the Gmail servers.

I might have found something for macOS users.
http://budiirawan.com/install-mail-server-mac-osx/

I will probably test this later. I need to produce a secure connection to Gmail/Outlook.com as well as bump up the TLS protocols used by the browsers below, stunnel seems to be a good idea but hard to set up. For 98 and 2000, would be easier to be able to run a newer version of Opera with KernelEx (12.18+) with the support for newer TLS protocols, but seems that it won't work.

Meanwhile, here's a list of my virtual machines and it's details for those interested:

Windows 3.11 For Workgroups
Virtualization: DosBox-X (macOS) & iDOS 2 (iOS)
Email Client: Outlook Express 5.0 ("speaks" only TLS 1.0, can't connect to Gmail/Outlook.com)
Browser: Internet Explorer 5.0 (no HTTPS, nothing apart of older HTTP sites)

Windows 98
I killed it. Security issues, browser issues with Vimeo and Youtube (and I spend most of my time watching and listening to music videos).

Windows 2000
I killed it. Security issues, browser issues with Vimeo and Youtube (and I spend most of my time watching and listening to music videos).

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Reply 83 of 109, by Bruninho

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Does someone have an idea on how to make dosbox think I am on a wired (ethernet) connection when I am on wireless conn. with the macOS? Probably Tun/Tap, but its complexity scares the shit out of me.

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Reply 84 of 109, by dr_st

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bfcastello wrote:

Does someone have an idea on how to make dosbox think I am on a wired (ethernet) connection when I am on wireless conn. with the macOS?

Why would DOSBox care? Maybe MacOS cares, but DOSBox?

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Reply 85 of 109, by Bruninho

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dr_st wrote:
bfcastello wrote:

Does someone have an idea on how to make dosbox think I am on a wired (ethernet) connection when I am on wireless conn. with the macOS?

Why would DOSBox care? Maybe MacOS cares, but DOSBox?

I mean Dosbox-X with NE2000 emulation. It only works when I use my ethernet connection, so I was thinking about how I could fool it to think I am on ethernet when actually I am on wifi. I did use a VMware Fusion linux VM with Dosbox-x installed, and it did work, but using a VM to overcome this is an overkill. Sure, I could do it directly in a VM without Dosbox, but VirtualBox has problems with SB16 emulation (crackling sound) and VMware Fusion does not have SB16 emulation for my DOS Games and WFWg311.

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Reply 87 of 109, by Bruninho

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keenmaster486 wrote:

You have to select the right network adapter in dosbox.conf.

my adapters are en0 (wifi) and en4 (ethernet). When I select en4 everything works well, but when I select en0 nothing works... Someone in this forum has said before that NE2000 emulation doesnt work with wifi well.

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Reply 88 of 109, by keenmaster486

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Actually now that I think about it there might be no way to do this unless you have a direct WiFi connection between two computers.

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Reply 89 of 109, by Bruninho

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WRP 4.3 improved massively - I managed to run a compiled binary on macOS and use it on a DOSBOX with WFWG 3.11 and IE5.

https://github.com/tenox7/wrp/releases/

Logged into gmail - well, sorta - but it really needs to find a way to magically turn form controls usable (inputs, textareas...). It's a bit slow. But works for most stuff, just not forms and videos (obviously, since WRP renders images of a page).

What WFWG 3.11 and IE/OE 5.0 needs is some sort of a SAFE "protocol downgrade magic" to be perfectly usable. OFC sites will never render properly because of scripts and CSS version, but being able to write and read my emails on Outlook Express would be enough for me.

EDIT 1: So far the only best solution is to run legacyweb.net on a rPi3 to do a stunnel4 for the email client, yet the configuration only works for only one email account. Also, it was not safe - the rPi3 was vulnerable and was attacked some weeks later.

EDIT 2: Even TLS 1.3 is not completely secure...
https://www.zdnet.com/article/new-tls-encrypt … -newer-tls-1-3/

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Reply 90 of 109, by keenmaster486

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There needs to be a way to use another computer as a "middleman".

Web Render Proxy is a major step in that direction.

But here's what it needs to be complete:

  • Acts as a standard HTTP or proxy server
  • HTML translator: translates modern web pages into old school HTML-only pages
  • Web Render Proxy functionality (optional, when the HTML translator can't cut it)
  • Email server: uses no security/encryption and can be configured to connect to modern services such as Gmail
  • Something that transcodes HTML5 videos to something old browsers can use, on the fly!

Maybe there's more I should add but this is the end goal sometime in the future, that I'd like to see happen.

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Reply 91 of 109, by Bruninho

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I'm trying to configure a stunnel on my macOS for use with DOSBox + WFWG311 + OE5.

I am almost there, I am hitting a wall, something in my stunnel.conf might be incorrect. OE can find my host and try to secure a connection, but fails to do so. I have even created a certificate for stunnel so I dunno what may be wrong.

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Reply 92 of 109, by Bruninho

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keenmaster486 wrote:
There needs to be a way to use another computer as a "middleman". […]
Show full quote

There needs to be a way to use another computer as a "middleman".

Web Render Proxy is a major step in that direction.

But here's what it needs to be complete:

  • Acts as a standard HTTP or proxy server
  • HTML translator: translates modern web pages into old school HTML-only pages
  • Web Render Proxy functionality (optional, when the HTML translator can't cut it)
  • Email server: uses no security/encryption and can be configured to connect to modern services such as Gmail
  • Something that transcodes HTML5 videos to something old browsers can use, on the fly!

Maybe there's more I should add but this is the end goal sometime in the future, that I'd like to see happen.

I managed to configure stunnel4 on macOS to use Outlook Express 5.0!!

https://www.sysadmin.md/how-to-access-gmail-s … th-stunnel.html

Simple and easy. I configured it, ran stunnel (probably need a reboot first) then loaded DOSBOX, WFWG, OE5. For it to work, I had to uncheck the boxes for SSL and change IP and ports to the ones I set on stunnel.

Asked OE to retrieve my emails. Nothing. Then I went to my Gmail account (OE5 is using my Outlook account) on my phone to send an email to myself. Sent. Back to OE5, asked again. My email came in. WOOOT WOOT! It is probably incredibly insecure, ATM, But I doubt someone is on my home wifi sniffing it. Anyway, that's why I set it for the outlook account - I never use it. (I could set for both Gmail and Outlook, but I'd rather not).

EDIT0: My next step is probably try to configure the rPi3 script I found last year for macOS to emulate an ISP. It works for my iDOS2 on my iPad Pro, so WFWG there can connect to the internet, since iDOS2 does not have NE2000 emulation. But I cannot keep the rPi3 on 24/7, or I might risk another attack. I'd like to see if someone can help to "translate" the script for macOS.

EDIT1: Since the outlook account credentials are the same I use for OneDrive, I might create a new account elsewhere. I have one on Yahoo, that should work better.

EDIT2: stunnel probably would also work for HTTPS on browsers if I can set it up too. I dunno...
EDIT3: Actually, sslstrip with some more stuff is a more appropriate tool for the job. Anyway, I think that if WRP improves the way keenmaster486 described above, WRP + STUNNEL should be the tools for older browsers and older mail clients.

Last edited by Bruninho on 2019-08-05, 04:41. Edited 1 time in total.

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Reply 93 of 109, by Bruninho

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@keenmaster486 : I finally figured out how to configure stunnel on macOS to help OE5.0 on WFWG3.11 (DOSBox) to connect to GMAIL!

It's super simple. Ignore my previous post. Here are the details:

1. Install stunnel (I used homebrew's stunnel, so "brew install stunnel");
2. Once installed, go to /usr/local/etc/stunnel and create a file named "stunnel.conf", make sure it's empty ("sudo nano stunnel.conf");
3. Paste the following content into stunnel.conf:

cert = /usr/local/etc/stunnel/stunnel.pem debug = 7 output = /var/log/stunnel.log client = yes […]
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cert = /usr/local/etc/stunnel/stunnel.pem
debug = 7
output = /var/log/stunnel.log
client = yes

[pop3s]
client = yes
accept = 110
connect = pop.gmail.com:995

[smtps]
client = yes
protocol = smtp
protocolUsername = YOUREMAIL@gmail.com
protocolPassword = YOURPASSWORD
accept = 9025
connect = smtp.gmail.com:587

4. Save the file, go back to the terminal and run "stunnel" (or "sudo stunnel", I don't know which one exactly worked);

5. Stunnel will show some info, so it's running. Now test it, you just need to configure OE normally, but instead set to use the ports above and the IP of your host machine instead of the pop and smtp addresses, and untick the SSL boxes. You can now send and receive emails on OE5.0 😀

NOTES
You also need to make sure your GMAIL account is set up to allow less secure apps. I recommend creating a new account for testing, and maybe to forward some emails.

After setting up stunnel and loading it, It's up to you keep stunnel as a background service (I prefer not). Also, if you feel lazy, you can test with telnet (make sure to install telnet with homebrew, because since High Sierra, there is no telnet installed). Just do "telnet localhost 9025" or "telnet localhost 110" and you will be greeted by gmail. To exit, simply hit CTRL + ] and type quit, ENTER.

Last edited by Bruninho on 2019-08-09, 19:04. Edited 1 time in total.

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Reply 95 of 109, by matze79

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Use a Shell Account to view your email ? 😀

there is even ssh for msdos.

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Reply 97 of 109, by Bruninho

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oeuvre wrote:

wait that's amazing, checking your GMail in Windows 3.11?!

What I did works for Gmail as long as you check "allow less secure apps" on.

For office365 emails I am not sure, I tried but for some reason it did not work to send, only receive. Same for Yahoo.

I created a new gmail account for that just to be safe, although I wanted to use an outlook account on office365. Looks like it only works with the premium accounts (I have one, but not going to use a daily driver email for that) since the premium ones have more security settings than normal ones. I believe you have to create an app password there. Same for Yahoo.

Basically with stunnel I can "upgrade" the protocol used in that connection with OE to GMail, from SSL3.0 to TLS1.x. For me it's enough for my emails.

I think that for web browsing, we don't have youtube, videos, and neither modern jQuery, HTML5 and CSS3.

IE5.0 would need something like a polyfill/modernizr for that. And newer video codecs. And a proxy for HTTP -> HTTPS "upgrade". So far the best we have is the WRP script.

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Reply 98 of 109, by Bruninho

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For those who want to try browsing with IE 4.0 / 5.0...

https://medium.com/@snoffeecob/bringing-inter … 19-84d030b75643

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Reply 99 of 109, by Bruninho

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Just FYI, gmail works without any workarounds with OE6.0 on Windows 98 SE. Just make sure you enable less secure apps settings. Remember, I am using a separate account just for testing.

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