I was writing up this question and in the process, it forced me to think a little harder and I answered it myself, though I still don't completely understand why it solved it.
I have an account on a shared host with 2 domains registered. I'm using the Asp.Net stack to run a few things like a blog and another site I am planning to kick off eventually. Both of my domains point to the root; the first is the original I used to signup, the second is a root domain pointer I added. Here is how I want it to behave:
Directory Structure:
Root (www.domain1.com) Root --\ Blog (www.domain1.com/blog) Root --\ Site2 (should be directed here if www.domain2.com) Root --\ Site2 --\ Junk (www.domain2.com/junk)
Right now, if you type in www.domain1.com or www.domain1.com/blog, that behaves as expected and I am fine with that. For www.domain2.com, I have the rewrite rule configured like this(from the web.config):
<rule name="Domain2">
<match url="(.*)(/)?" ignoreCase="false" />
<conditions logicalGrouping="MatchAll">
<add input="{HTTP_HOST}" pattern="(www\.)?domain2\.com" ignoreCase="false" />
</conditions>
<action type="Rewrite" url="/site2/{R:1}" />
</rule>
That rule is supposed to match any path if the host is domain2.com, pick off the path to the requested resource and format it properly. So when somebody types www.domain2.com/junk/default.aspx, in IIS, this resolves to www.domain2.com/site2/junk/default.aspx without the user ever knowing. This is mostly working as advertised except when the user does not type a trailing slash in a subfolder. IE:
www.domain2.com (works)
www.domain2.com/ (works)
www.domain2.com/junk/ (works)
www.domain2.com/junk (doesn't work!) IIS 7 looses its brain here and formats it out like www.domain2.com/site2/junk because a 2nd request is automatically issued for the trailing slash and a 404 happens.
So, I updated the action to be:
<action type="Rewrite" url="/site2/{R:1}/" />
This seems to have resolved it, but why doesn't IIS 7 now spit out www.domain2.com/junk2/default.aspx/ ? How does it know not to append a trailing slash to a document extension?