@TReKiE I’ve run a Microsoft root cert upgrade package with a signing date of 2011, reckon that’d be modern enough?
Edit: I’ve now drag/dropped the 2013 WinXP .sst files onto the Win98 cert update tool, I assume that worked, it didn’t throw an error…
@OhHelloThereImTheGuy Yeah, it’s more robust than I thought, it will continue just fine if you dismiss the .net debug box that shows up, though some other functionality is broken (like certificate generation), so I’m giving KernelEx a shot to see if that helps.
Edit: Well, that’s a bust. Fiddler (whether it would’ve been useful or not) actually fails to run under KernelEx, who’d have thought it’d run better in Win98 mode? 
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To install MSN Messenger on Win98:
1st step: Download VirtualPC (Vista/7 only) or VMware
2nd step: Install Windows 98 and VMWare Tools/VM Adittions
3rd step: copy the MSN v1, 2 or 3 to the VM (make sure when you are sign up you enabled the option "Old MSN support"
4th step: Log in on Messenger
5ft step: Enjoy
You can get 4.6 working on 98
Sorry to bump this 4-month old thread, but I’ve done some actual research on the topic and I’ve gotten somewhere with the problem.
From what I’ve read, 9x itself only support SSL 2.0 (and maybe 3.0), and if you don’t have 98 SE or IE 5.5 installed, then it won’t support anything else. If IE 5.5 is installed, then when TLS support is enabled, connecting to Escargot’s web services will still backfire since the oldest TLS cipher suite Escargot supports is TLS_RSA_WITH_3DES_EDE_CBC_SHA, and 9x doesn’t support RSA. If I can find any suitable TLS cipher suites for 9x (and XP installs with IE < 8), I’d be glad to bring them up here.
Even though it may seem that I’m regurgitating old info with minor details sprinkled in, here’s where the new discovery comes in (at least in public). Escargot doesn’t have any kind of SSL support, which means that non-TLS compatible installs of 9x won’t be able to connect to Escargot’s web services at all. Although SSL is prone to vulnerabilities nowadays, I feel that Escargot should aim to be compatible with as many legacy systems as possible, since these are old applications we’re dealing with that are expected to work on these old systems. It’s especially important considering the upcoming Yahoo! Messenger frontend utilizes web frontends for some of Yahoo!'s features, one being creating and deleting aliases, and having those features inaccessible on one of its target systems wouldn’t make much sense. If I had more expertise and time to dig into what cipher suites 9x and XP support, then I’d be able to pitch a possible solution to @valtron. 
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Then how am I successfully running MSN 3.6 under Windows 98?
If I’m correct, MSN 3.6 works on 98, but I’m not sure about this.
Update IE to it’s latest version supported and try.
3.6 uses MD5 auth, so no HTTPS required. It’ll work on 98 no problem.
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3.6 is the highest version I could run successfully on 98. Version 4.7 and higher requires Windows XP. Though, I can’t seem to sign in on Windows XP without getting the dreaded 8004821 error.
4.6 is the latest version of MSN that works with Escargot on 98.
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4.7.0106 is the last version of MSN which will run and connect, as every version following that runs into TWN. Evidently, we’re seeing now the limitations of Escargot server. Have we looked at our agreements recently? Transport Layer Security - Wikipedia
It’s not really a limitation of Escargot itself, but more of the production server valtron uses for HTTPS, named Caddy, which only support TLS and a few of the old ciphers for it. As far as I know, he won’t be switching to something a bit more flexible in legacy compatibility in the near future.
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