I have read this question and this page linked to in the question, as well as dozens of other articles about debugging asp classic with VS but it's still not clicking for me.
I am using VS 2010. The files I want to debug live on a remote server. I have installed the Remote Debugger on the server. I opened the website and attached to the w3wp.exe process on the remote machine. I created some breakpoints but I am still getting "The breakpoint will not currently be hit. No symbols have been loaded for this document" on those breakpoints. Is that the problem or is that a symptom of a larger problem with what I am doing?
First, by default, when you open a web site in Visual Studio, you're opening it via the file system, not via IIS. If this is the case, then Visual Studio uses the internal Cassini web server, rather than IIS.
The Cassini web server does NOT run classic ASP. IIS does. So the first thing you need to do is figure out how to debug in IIS.
It should go without saying, you need to have IIS installed on the machine you're working with, and have the web site you're debugging set up the same as it would be on the server. (so you should be able to run http://localhost/somepath
and be able to see your site)
You also need to attach to the running process of Internet Explorer. There's a link to that as well.
Next, you need to get Visual Studio to attach to IIS and execute the web site rather than use the built-in web server and enable debugging.
That's covered here: This topic is no longer available (which is the first child link of the page you liked to in your question here.
From there, you should be able to follow the remaining links and get up and running.
Edit - added
This article takes you through it step-by-step. Debugging Classic ASP ( VBScript ) in Visual Studio 2008
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