I am trying to build an iPhone web application using ASP.NET. The page is dynamically rendered once for each visitor. At this point the page can be bookmarked and it will never
It could be to do with the size of the output.
I can't talk from any serious experience in tweaking things specifically for an iphone, but there is an intersting read from the YUI team here: http://yuiblog.com/blog/2008/02/06/iphone-cacheability/, which indicates that the largest unzipped cache file that can be held in an iphone is 25k, and that for optimal caching, as many components as possible should be <25k.
That may be the cause of your problems, but that's only a guess.