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Trying to serve IIS files on a Mac - IIS seems to see directory structure but not individual files

reasonable information technology management practices

In the question, I am setting up a local instance of Classic ASP to migrate massively aging architecture. This is a good thing. There are plenty of companies on extreme legacy hardware that needs to be migrated, some of it Classic ASP, and for people that have to deal with the annoying task of rewriting old codebases, like myself right now - questions like this have utility.

I never, in the question, suggest running Classic ASP is a smart idea - I think it's a terrible idea, and I have told the company in question this in no uncertain terms, which is why they have hired me to migrate it. But I can't change the fact that that's what they're currently running, or that I need to run Classic ASP locally temporarily to ensure that the migration is correct and doing everything the old code did.

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    Classic ASP wasn't the reason. Running IIS on Windows 11 hosted on a Mac and data files on a network drive...checks a number of boxes.
    – Greg Askew
    Commented Jan 26 at 12:13
  • @GregAskew It doesn't, though. It's a LOCAL environment for development. The "network drive" bit isn't actually a network drive, it's how the virtual machine represents my actual Mac's physical hard drive. This is a perfectly reasonable setup for local development and testing. The only reason it doesn't work is because the VM software represents the parent drive as a network drive rather than a physical drive. It doesn't "tick any boxes" - why would I use another machine for development, when I am literally just replicating the original site so it can be migrated to modern frameworks?
    – Andrew Alexander
    Commented Feb 7 at 16:39
  • @GregAskew Like none of this will ever see production, it's entirely so that I can analyze the codebase and database locally, write the migration and keep feature parity
    – Andrew Alexander
    Commented Feb 7 at 16:43
  • @GregAskew I think you, or whomever disabled the question don't actually understand the setup. There's no actual "network drive". Both the VM AND the files are on the same physical drive. The VM doesn't "know" that of course, but that's the actual reality. And using a VM for doing development in a different development environment is standard practice, and I'm certainly not going to setup a different machine for this when it's literally being used to replicate a site in order to migrate it. That would be a terrible idea. This IS best practices for what I am trying to do.
    – Andrew Alexander
    Commented Feb 7 at 16:55
  • Also important to note that Microsoft themselves have given advice for a configuration similar to this (the only difference being the network drive representation). If Microsoft sees no issue with recommendations for this config (IIS running on virtualized Windows on a Mac), then I see no reason why Server Fault should. I use virtualization constantly for Linux server development with Docker containers, why would I not also use Windows virtualization?
    – Andrew Alexander
    Commented Feb 7 at 17:06
  • don't actually understand the setup. There's no actual "network drive". Both the VM AND the files are on the same physical drive. I understand. I use mklink on VM guests to access shares on my host, also for development purposes, for IIS. But I wouldn't use this forum to discuss it. More of a SuperUser topic. This is trivial to do on Windows btw.
    – Greg Askew
    Commented Feb 8 at 10:11
  • Welcome to ServerFault! I have up-voted your question. Most of the time, the only reason questions are closed is because certain high-rep users have too much time on their hands and enjoy harassing low-rep newbies here.
    – Jesse Nickles
    Commented Apr 7 at 7:06

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