"And that is why, in 2009, when developing in Microsoft .NET 3.5 for ASP.NET MVC 1.0 on a Windows 7 system, you cannot include /com\d(\..)?, /lpt\d(\..)?, /con(\..)?, /aux(\..)?, /prn(\..)?, or /nul(\..)? in any of your routes."
I'm pretty sure you could still do this up until at least Win2k+ if your mapped printer had a port associated.
That also explains why you shouldn't use LPT1 as file name - it was a special name that meant first parallel port. I remember seeing a ridiculing thread about it on HN some time ago