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Would it be worth your while to add the option to specify multiple StartFiles?
When rolling out hiawatha in a generic hosting environment I notice that have the desire to specify three startfiles: index.html, index.php and index.htm (in that order).

For every (virtual) host, you know what the start file is. So, there is no need for multiple start files. If a certain directory has a different start file, you can specify it via a .hiawatha file.

I have multiple servers running with a lot of websites. They all work fine with a single start file.

Having multiple start files does not really go nice with how Hiawatha works internally. So, at the moment I have no intention to implement it.

In an ideal world, you are right. However, I have to deal with customers which tend to mix-and-match and do not follow instructions very well (your typical customer never does, sadly).

I.e. they tend to create several subdirectories, and expect every subdirectory to just work automagically. They do not know about .hiawatha files, the concept is too difficult to them. They install different packages in different parts of the tree; some of these packages typically use index.html, others use index.php and yet others use index.htm as their default pages at various points in the tree.

In order to host a website for customers like this, one basically has to make the webserver intelligent enough to deal with this. The days where I had the luxury to tell the customer to RTFM are long gone (sadly).

Anyway, I've looked at the code, you'd need to support some kind of list where currently just one string is stored in the configuration structure; it's fixable, it just takes longer than 20 seconds to fix. Any objections if I'd fix it at some point in the future (if I get annoyed enough by the URLtoolkit workaround I am using at the moment)?