Checking my mail in Outlook 2000 on WinXP

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Checking my mail in Outlook 2000 on WinXP

Post by rsade95 »

I've been experimenting with running Office 2000 products on WinXP inside VirtualBox. Office 2000 actually runs decently well on Windows 10, but it's much smoother in WinXP for obvious reasons.

I'm dead set on getting IMAP/POP3 to work in Outlook 2000 so I can actually manage my real email account. Of course, nothing about what I'm trying to do is supported or considered possible by anything or anyone. I just want to do this for my own enjoyment. I've used OE Classic before but that just doesn't scratch the same itch. As expected, gmail, yahoo, and outlook (and probably any others) email accounts cannot send/receive mail in Outlook 2000 after I set them up.

Internet connection works fine inside VirtualBox, so there should be a way to make this work.

Just to confirm that things are setup properly in Outlook, here are my Yahoo IMAP account settings:

Server Information -

My incoming mail server is a IMAP server

Incoming mail (IMAP): imap dot mail dot yahoo dot com

Outgoing mail (SMTP): smtp dot mail dot yahoo dot com

Incoming Mail Server -

Account name: myemailaddress@yahoo dot com

Password: **********

Log on using Secure Password Authentication: Unchecked

Outgoing Mail Server -

My server requires authentication: Checked

Server Port Numbers -

Outgoing mail (SMTP): 465

This server requires a secure connection (SSL): Checked

Incoming mail (IMAP): 993

This server requires a secure connection (SSL): Checked

With everything setup in Outlook 2000 as shown, I click Send/Receive and then get a popup with the following error message:

Could not fetch new headers in the inbox for Yahoo IMAP. An unknown error has occurred. Please save any existing work and restart the program.

I'd like to know if there are any utilities available to help make this work. If there is a specific email provider that could allow this to function, I would be happy to start using it.

Thanks for your time!
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Re: Checking my mail in Outlook 2000 on WinXP

Post by FranceBB »

The error doesn't really tell me much, but on top of my head I think it might be an handshake problem.
When the client connects to the server it performs an handshake as part of the normal TLS authentication scheme: the server exposes a list of supported ciphers that it can accept and the client does the same.
There are lots of ciphers that can be used however the year 2000 was a very different time and most of the ciphers that were still supported back then like DES are considered broken now. Assuming that Outlook 2000 can't perform AES256, what I think is happening is that the server is probably saying "I can do AES256 and ChaCha20" while outlook 2000 is saying "I can do DES" and they don't match, so the server replies "no can do, kiddo" and the connection fails during the handshake process.
Mine is just speculation, though.
On this regard, this isn't a virtualbox problem per se, so I think you're better off asking the same question on MSFN in the Windows XP section. There are way more XP knowledgeable people there.
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Re: Checking my mail in Outlook 2000 on WinXP

Post by birdie »

This is a question for, not for these forums as it has nothing to do with VBox.

WindowsXP by default doesn't support TLS and SSL 3.0 has long been deprecated.

There is an unofficial past SP3 service pack for XP which adds TLS support, you could try it: ... icial.html
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Re: Checking my mail in Outlook 2000 on WinXP

Post by fth0 »

FWIW, SSL 1.0, SSL 2.0, SSL 3.0, TLS 1.0 and TLS 1.1 are all deprecated nowadays, only TLS 1.2 and TLS 1.3 are acceptable TLS transports. So you'll have to find a common ground between the Windows XP Outlook 2000 combination and an email provider.
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