this post was submitted on 03 Oct 2026
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I had completely forgotten just how awful microsofts websites were back in the early 00's. Gates saying the site kept timing out or would go down all time is very much true and happened with everyone. Microsoft's website would CONSTANTLY time out. downloading ANYTHING via microsoft was an absolute crap shoot if it would actually download or not.
I remember having a computer in the late 90s that only came with Netscape. In order to play games like X-Wing vs Tie Fighter online more easily than direct IP connection to someone you had to use Microsofts Internet Gaming Zone. in order to use that you HAD to have Internet Explorer, it wouldn't work with Netscape. So you'd have to spend an entire day downloading IE and MOST of the time the download would time out or crash so THEN you had to use a download manager to prevent you from losing progress on the download for when Microsofts site would go down which again, was constantly. updating the OS was even more painful as again Microsofts online service would always go down.
If you think Microsoft is bad now, man it was A LOT worse back in the day for reliability.
Omfg, and let us not forget that it was the world's biggest knowledge base containing precisely zero quantifiable knowledge.
yup if something went wrong with Windows you might as well just try to fix it based purely on hopes and dreams or pray to whatever god you believed in that there was someone who knew the answer in some random IRC room. the "troubleshooting" crap on the MS website was absolutely worthless. and chances are the site would just timeout on you before you could actually find anything.
My mom basically found herself as the person who fixed printers at the school at which she worked, and this was before anybody had much of a clue about computers (our family was kind of ahead in tech).
She ended up getting some free "MS tech net" subscription which I used, it was just as worthless as the public facing stuff. I will say though, back when having real ms software actually meant something, having access to infinite license versions of most of their stuff was pretty cool.