Adam,

Creating a virtual directory named "mockup" under \\fileserver2\sharename\Inetpub\wwwroot\ and pointing it to \\fileserver3\sharename\Inetpub\wwwroot\siteName\mockup\ did solve my problem of the images not appearing after I save the changes (as stated in Scenario 1 of the first post in this thread).

I'm guessing that this is a test you wanted to see the result of. It worked, which is great, but I'm not surprised since the creation of this additional virtual directory named "mockup".

The reason this isn't a viable long-term solution is because we have various different content at that directory level (\\fileserver3\sharename\Inetpub\wwwroot\siteName\lots of different folders here with content) and we don't want to introduce the ongoing maintenance tasks of creating a new virtual directory for each one, creating new virtual directories each time a new content section is added, etc. I hope that makes sense...so in other words we really want to just have the one virtual directory named external which points here:  \\fileserver3\sharename\Inetpub\wwwroot\siteName   ...and we then programmatically pull in the content folder name (in this example "mockup") from SQL Server at runtime.