I don't think it's possible at all considering changes to SSL and TLS encryption over the years and retirement of older versions...
If transferring files is all you need why are you not using built-in windows networking?
Old school FTP might also be easier and faster to setup.

Gmail has a setting to enable older encryption methods to make it work. Not sure if MSN has that.

I don't think there is a way to get it to work.
You might have better luck with something like Eudora though.

Email isn't for transferring files but anyway:
Thunderbird 12.0.1 works in Windows 2000 and is alot newer than Outlook Express 6.
If you are dead set on OE6 you could probably setup a proxy if you can't use the non-encrypted ports.

If you want to use email via a website in a browser then New Moon 26.5 works in vanilla Windows 2000.
http://o.rthost.win/gpc/files1.rt/palemoon-26 … 0814.win2000.7z

Couldn't you just dual boot (or USB/CD/DVD live boot) into a Linux distro that supports newer mail clients ?

Another option is to use an E-mail client on an Android or IOS phone and then copy the files to a USB flash drive which can be connected to the Windows 2000 machine for the actual transfer .

Also, don't take this the wrong way, but I am curious as to why you are using Windows 2000 for this to begin with in 2022 .

darry wrote on 2022-03-10, 00:01:

I am curious as to why you are using Windows 2000 for this to begin with in 2022 .

Me too, but I do think it's cool 😁

Personally I'd chuck War FTP on the laptop and Filezilla on the modern rig.

chiveicrook wrote on 2022-03-09, 22:12:

I don't think it's possible at all considering changes to SSL and TLS encryption over the years and retirement of older versions...

You can't use OE6 directly with most e-mail providers anymore due to old unsupported encryption.

However, I did have a working setup once, using a Raspberry Pi with Perdition mail proxy installed on it. OE6 connected (without encryption) with RPi, where Perdition added appropriate encryption and connected with Gmail.

So it is possible to use OE6, but you need something (any Linux machine would do) as a proxy between the old and the new.

keenmaster486 wrote on 2022-03-09, 22:25:

Gmail has a setting to enable older encryption methods to make it work. Not sure if MSN has that.

All I know is that Gmail has "less secure apps" setting, but it's not enough for OE6.

Look here : https://www.oeclassic.com/

Hi all,

Thank you for all your replies and I am sorry for responding this late. Why do I use Windows 2000? Because it is the best Windows version ever released and it does everything I need it to do. It performs way faster on a netbook than any newer Windows version, including XP. On top of that there is a possibility for some early Windows games on the go with Windows 2000. I also love using the no-nonsense versions of Microsoft Office like Word 95 and PowerPoint 95. Over the years I have had different Windows versions on netbooks, 7 Starter, XP Professional, XP Home Edition, but nothing works as well for me as Windows 2000. And I am not missing out on much, because Windows 2000 is pretty compatible with XP-software and drivers. I will admit though that Windows 2000 will become less and less compatible in the years to come. On top of all of this, there is something I just love to do: pushing my favorite old hardware and software to their limits.

I use a Linux netbook as well. I use it more than the Windows 2000 netbook actually, but Lubuntu really has issues with connecting to a projector properly. With duplicating Lubuntu uses only a quarter of the screen area and with extended desktop it does work better, but then I don't see anything myself. The only things that I don't like about my setups is that neither can run Microsoft Teams and neither can run web applets very well. The latter one being mostly because of hardware limitations. Luckily these are just my portable setups. At home I do all of my work on a Core i5 4th generation with a Linux Mint 19/Windows 7 dual boot.

I have considered FTP, but the thing is that I also want to be able to receive files from peers, so e-mail is really where I am at. At home FTP is a great option of course. Dual boot would be an option if I had a bigger SSD in there, but 8GB really isn't a lot. That basically leaves me two options: using another e-mail client or setting up a proxy.

I just had a look at Perdition, but I fail to find any Windows release on their website. Is there a proper Windows alternative for Perdition?

I also noticed some great alternatives were mentioned like, Thunderbird 12, Eudora and OEClassic, but because of my limited disk space, I will try first to get OE6 running. Running e-mail in Pale Moon is an option, but then I am kinda in web applet territory, which is a real pain on a VIA C7-M with 900MB of RAM (There is a 1024MB stick in there, but somehow it only sees 896MB). Even on my Linux laptop (Atom N550 with 2GB of RAM) using webmail is a pain, so I can imagine that it will be even more of a pain on this laptop.

The missing ram is probably shared with the GPU.

Well, then there's always the true nerd way: alpine 😀 Never tried it on windows but builds are released officially and there are guides on the web with configuration details for outlook/gmail/etc .

chrismeyer6 wrote on 2022-03-11, 13:52:

The missing ram is probably shared with the GPU.

This makes a lot sense! Why didn't I think of that myself?

I ended up installing Thunderbird 12.0.1 and it works just fine. I also installed the Pale Moon browser just in case I ever need to do some basic web browsing . Thanks for all of your help! 😀

Just curious can your laptop support 2 gigs of RAM? That could help with web browsing give windows 2000 and the web browser a little bit more breathing room.

I think the laptop does support it, but sadly I don't have a spare 2GB module lying around. I only have spare 1GB modules. I think a RAM upgrade would be a good idea though, so I am gonna try to find a 2GB module for cheap. I only paid €12,- for the laptop, so I don't want to spend big. 😜

About Outlook Express 6... https://forums.macrumors.com/threads/are-ther … y-2022.2337982/

But... I have some tricks under the sleeve for these things, I haven't used it for a while, so I don't know if they really are still working as of 2022:
Re: Logging into Gmail with old mail clients

Bruninho wrote on 2022-03-16, 02:03:

About Outlook Express 6... https://forums.macrumors.com/threads/are-ther … y-2022.2337982/

Not even Outlook 2016?
I think I'll consider gradually retiring GMail as my main account because of their hostility towards e-mail clients.