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Logging into Gmail with old mail clients

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First post, by keenmaster486

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I mentioned this in my Thinkpad thread but I think this issue deserves its own thread.

I can't seem to get Outlook Express 5 to log into Gmail, even though official support and some internet research says it should be possible. I'm using IMAP for incoming and SMTP for outgoing. Now, I don't think the issue involves IMAP in particular. The same problem would present itself with POP. The error always has to do with not being able to "establish a secure connection to the server", which I take to mean that SSL is not working on Google's end. I can neither send nor receive mail; both throw the same error. Supposedly this is still up and running as long as you check the box for "access for less secure apps" which I have done. And in the past it has indeed worked for me. But somehow I can't make it work this time no matter what settings I try.

I'm using the official Google support page settings:

Incoming:
imap.gmail.com
SSL required
Port: 993

Outgoing:
smtp.gmail.com
SSL required (but they recommend TLS/STARTTLS): Yes
Port for SSL: 465
Port for TLS/STARTTLS: 587 (but I'm not using this, only SSL)

Username: my full email address
Password: my Google account password

And it is not working. I've reentered all the settings multiple times to make sure I'm not doing something wrong.

I've tried this from my old Thinkpad running Windows 3.1 and Outlook Express 5.0 16-bit, and a virtual machine running Windows 98 and Outlook Express 5.0 32-bit. Both have the exact same results.

I found a guy somewhere on the internet who claims he got it working with both OE 5 and 6, from earlier this year. But he didn't document his process.

I can't figure this out. I'm beginning to think that Google simply disabled SSL permanently without telling anyone, and the "allow access for less secure apps" switch doesn't actually do anything any more.

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Reply 1 of 101, by keenmaster486

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Here's a short update:

I tried this in Outlook Express 6.0 in Windows XP just now. And... it logs on with no issues. I put in the exact same settings! I can't even find any additional settings in 6.0 compared to 5.0. It looks identical. Literally no difference. And yet it works in 6 but not in 5. Very frustrating!

I flermmed the plootash just like you asked.

Reply 2 of 101, by Zup

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Keep on mind that there are a few versions of both TLS and SSL layer, and some of them has been deprecated because of security flaws.

Maybe your Windows 3.x is trying to talk to GMail with a version too old to work.

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Reply 3 of 101, by DosFreak

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You'll likely need to use a proxy or stunnel or similar.

XP supports TLS 1.0 but can support TLS 1.1 and 1.2 with the POS update. For any previous Windows OS only TLS 1.0 and earlier and the ciphers are likely deprecated.

To more easily troubleshoot these kinds of errors use wireshark or similar tools.

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Reply 4 of 101, by yawetaG

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Zup wrote:

Keep on mind that there are a few versions of both TLS and SSL layer, and some of them has been deprecated because of security flaws.

Maybe your Windows 3.x is trying to talk to GMail with a version too old to work.

It's very likely that this is the problem, especially considering that various companies have discontinued the use of older SSL versions in the last year. On Unix-likes (including Mac OS X; use Homebrew) you can compile and install the latest version of OpenSSL to fix the issue. For Windows and other old systems you might be out of luck if you can't get any of the binary distributions to work.

Reply 5 of 101, by keenmaster486

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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.

I flermmed the plootash just like you asked.

Reply 6 of 101, by keenmaster486

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An update:

I think it might be 128-bit encryption. IE 5.0 does not support it out-of-box, but there is an update you can get for Windows 3.1 that updates the system files to support it.

If you want it for Windows 98 it seems you have to get IE and OE 5.5. I did so, and that immediately fixed the problem.

I have a hunch that the 128-bit encryption update will also fix Outlook Express 5.0 on Windows 3.1.

I flermmed the plootash just like you asked.

Reply 7 of 101, by keenmaster486

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Well, I installed the 128-bit encryption thing on WFW 3.11 with OE 5 and it still doesn’t work. Disabling SSL 2.0 (leaving SSL 3.0 as the only protocol enabled) produces a different error: “server unexpectedly closed connection,” the same error I get when I disable SSL altogether. It’s almost as if OE 5 is trying to use SSL 2.0 instead of 3.0 even though 3.0 is available.

OE 5.5 still works. The question is, what changed under the hood from OE 5 to OE 5.5? I can’t find any differences in the settings.

I flermmed the plootash just like you asked.

Reply 8 of 101, by yawetaG

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Just an idea: It could also be that the server terminates the connection based on the user agent string. You can test this using a program that can spoof that string.

But yes, Wireshark. Second that.

Reply 9 of 101, by keenmaster486

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tojavu wrote:

could be. but why would one want to use such a old emial client. there a re new old looking email clients out there like evolution.

tyTc1Nl.jpg

Edit: how would I spoof the user agent string in Windows 3.1?

I flermmed the plootash just like you asked.

Reply 10 of 101, by gdjacobs

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For really old software that only allows older, insecure versions of SSL, why not setup a local relay device?
emailrelay.sourceforge.net/
plus
pyropus.ca/software/getmail/

Or if you want a fun time, just build it using postfix.

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Reply 11 of 101, by bfcastello

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gdjacobs wrote:
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For really old software that only allows older, insecure versions of SSL, why not setup a local relay device?
emailrelay.sourceforge.net/
plus
pyropus.ca/software/getmail/

Or if you want a fun time, just build it using postfix.

any tutorial on how to do it? I have a raspberry PI 3 serving as a fake ISP for my dosbox WFWG 3.11, connected through Trumpet Winsock. I can get to a few http sites, but not https and at least I can use mIRC (amazing!!!). But emails is impossible. I wanted to use windows mail or outlook express.

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Reply 12 of 101, by keenmaster486

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I don’t think Windows Mail is possible, as it only will connect to MS Exchange Server. Unless you could run MS Exchange Server on a Raspberry Pi.

I flermmed the plootash just like you asked.

Reply 13 of 101, by gdjacobs

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bfcastello wrote:
gdjacobs wrote:
Show quote

For really old software that only allows older, insecure versions of SSL, why not setup a local relay device?
emailrelay.sourceforge.net/
plus
pyropus.ca/software/getmail/

Or if you want a fun time, just build it using postfix.

any tutorial on how to do it? I have a raspberry PI 3 serving as a fake ISP for my dosbox WFWG 3.11, connected through Trumpet Winsock. I can get to a few http sites, but not https and at least I can use mIRC (amazing!!!). But emails is impossible. I wanted to use windows mail or outlook express.

Here's half of the solution:
https://unix.stackexchange.com/question ... mtp-server
You'll also need fetmail or getmail (recommended as it's not a buggy mess) to pull messages into your maildir.

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Reply 14 of 101, by detritus olentus

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I've had some luck using a program called Pegasus Mail in windows 98. Their site says 3.1 is supported though I've never tried it.

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Reply 15 of 101, by bfcastello

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detritus olentus wrote:

I've had some luck using a program called Pegasus Mail in windows 98. Their site says 3.1 is supported though I've never tried it.

Doesn't work for Windows 3.11 for Workgroups - because protocols. Same reason for Outlook on it.

I know it does work for W98, though. But I want to use 3.11, I don't have good memories from 95/98 - only 3.11 yeah. Anyway thanks for your suggestion, I tried it, I probably didn't configure it properly, but it just could not work there.

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Reply 16 of 101, by bfcastello

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gdjacobs wrote:
Show quote
bfcastello wrote:
gdjacobs wrote:
Show quote

For really old software that only allows older, insecure versions of SSL, why not setup a local relay device?
emailrelay.sourceforge.net/
plus
pyropus.ca/software/getmail/

Or if you want a fun time, just build it using postfix.

any tutorial on how to do it? I have a raspberry PI 3 serving as a fake ISP for my dosbox WFWG 3.11, connected through Trumpet Winsock. I can get to a few http sites, but not https and at least I can use mIRC (amazing!!!). But emails is impossible. I wanted to use windows mail or outlook express.

Here's half of the solution:
https://unix.stackexchange.com/question ... mtp-server
You'll also need fetmail or getmail (recommended as it's not a buggy mess) to pull messages into your maildir.

Let's say what if I had already configured them ? How do I set up my outlook account to use them?

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Reply 17 of 101, by gdjacobs

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Depends on what choices you make. Potentially clear text SMTP and POP3 settings to your relay server with no encryption at all, but definitely make sure the server is well filtered from your internet connection.

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Reply 18 of 101, by wiretap

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Google also sometimes blocks "less secure" applications. For accessing via retro machines without the proper security measures available, look here for how to allow less secure apps to access your Google account: https://support.google.com/accounts/ans ... 0255?hl=en

I have a dedicated retro Google/Gmail account that I use for accessing via my XP and older machines. All of my modern Google/Gmail account stuff forwards to it. I just turned on "allow less secure apps into your account" and it works from DOS/Windows 3.1 and up. i.e. I can use any mail client with Gmail, via SMTP or POP3/IMAP. I even used Gmail up until last year on a Windows CE Jornada.

Also, I keep this stuff on a separate LAN outside of my normal more secure home LAN, just in case some obscure worm/virus gets through.

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Reply 19 of 101, by gdjacobs

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

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