Yeah, IIS didn't have any sort .htaccess type thing for url routing IIRC. Even later on, we had to dig under the hood of asp.net because we didn't want .aspx in our paths.

It definitly could have it, provided someone wrote an ISAPI extension/filter combo for it.

I got to know, because I wrote a complete proxy on top of ISAPI, with callback handlers that could be written in C or Tcl.

On Windows NT and 2000, for our application server based on top of IIS (we had a version on top of Apache as well).

Yeah, it's a module in Apache too, it just comes OOB, so 'LAMP' had a cheap routing/rewrite solution. (ASP.net had APIs for that kind of stuff, so that was probably MS's original answer.)

I believe it was Windows Server 2008 that brought URL rewriting support to IIS.

But by then ebay wouldn’t be using ISAPI :)