I thought it’d be fun to go online with my Win98 desktop that I purchased in 1999.
Gonna format and reinstall the OS and all the software/virus protection that came with it, as if I just unboxed it in 1999, but no software after the year 2000.
How long do you estimate it will be before it grinds to a halt with malware and virus’s?
It depends on where you go on said internet.
No place that would be obvious malware bait. I’m not purposely trying to get infected. Pretty mainstream sites. I know that’s a vague answer and in the eye of the user.
It is hard to say but it depends on what is on it. Computer viruses are not like human viruses. They don’t just evolve to become more and more destructive retroactively. They are generally designed to target the most popular operating systems and applications of the day. Windows 98 is really old so there aren’t going to be a lot of places still trying to transmit viruses to a computer running it. It should still work fine for any sites that support versions of Internet Explorer or even Netscape that old but there will be a whole lot that won’t. Locally installed software designed for Windows 98 should still work fine.
That said, you don’t need viruses to cause Windows 98 to self-destruct. It could do that just fine on its own. It was like a heroin addict after a bad break-up. It is possible to make it a little stable though. We have a couple of really obscure machine controllers at work that run both Windows 98 and Windows 95 that work most of the time but they aren’t connected to any sort of network and are stripped down to only do exactly what they need to.
Aside from malware and viruses, that old computer is going to choke on modern websites.
Windows 98 had an obscure glitch that caused the operating system to freeze up after 50 days of continuous operation. The problem went undiscovered for years because nobody could keep it running for that long.
One question along with this–are you connecting directly to the internet, or are you connecting to a more modern-type home network where you have a router handing the ISP connection and providing NAT for the desktop?
The latter will prevent a lot of the crap that might otherwise hit your system.
This. I have an early 520c that I still use now and then. Being Mac viruses aren’t an issue but the usual web-page is beyond its capacity to handle. The old AOL dial-up e-mail pages are about its limit and a few other crude sites. Forget shopping or anything like that.
Definitely, plus whenever the browser being used starts to load updates he’ll run out of disk or thrash himself to death. I went through this with a computer my daughter’s riding coach had - very old, very full. She had viruses, but they were the least of her problems.
For a truly authentic experience, a dial-up connection is mandatory. 
Ethernet to router. (although I wonder if a USB Wi-Fi adapter would work with Win98 and those old USB ports?)
Nope. I actually first got broadband in 1999 when I bought that computer. 1MPS cable modem. Not much these days, but in 1999 it was amazing.
Well I know that an unpatched version of xp will be part of a botnet within seconds of connecting to the internet so somewhere in that range. Your only saving grace is there are probably fewer scanners looking for Win 98 computers.
If you use it to log onto Straight Dope? 37 milliseconds.
I came to the dope and posted using Internet Explorer 1.0 under Windows 3.11 for Workgroups, just the other day.
I suspect there isn’t much risk of exposure to Windows 3.11 compatible viruses.
That’s not very fair.
A lot of the malvertising hosted here takes MUCH longer to load, along with the entire rest of the page.
In 1999 on my state university’s network, the mean time to infection on an unprotected computer was 7 seconds.
I’ve never had a malware infection from a network source. I got hit by some viruses in the floppy-disk era, and I helped de-virus some customer’s computers from a CD-borne virus in the late 90s, but never got one from a web browser or email.
I think (but I may be wrong) that a really old OS might be marginally safer (that is, slower to succumb) than a newer one - simply because the population of infectious agents out there is probably skewed towards the sorts of malware that infect newer OSes that maybe haven’t been patched for a year.
If there are exploits that are capable of infecting, say unpatched Win7, they might be attacking a vulnerability that has always existed in… I dunno… Microsoft’s implementation of the TCP stack since the year dot - and in that case, your Win98 machine could fall foul of them.
But I think a significant chunk of malware isn’t going to traverse the NT/9x boundary. There will still be malware out there waiting for Win9x machines to appear, I guess, but on balance, I think an unpatched WinXP machine will fall faster, and harder than a Win98 machine.
Not bother trying to install virus protection it do nothing for most of the malware out there these days on the internet.
The virus protection are only good for the malware floating around in the 90’s.
Windows ME was that junkie a few years later, on her third methadone series, breaking down at the clinic while crying “just give me my medicine, damn you!”