Here's a classic "works on my machine, but not in production" scenario.
ASP.NET app written in C#. Simple UI with some items to select. Once the user clicks "Go", it runs to the server and builds a PDF file with some data-driven graphics in it (housed in SQL Server) and sends the PDF back to the user for use.
I think it's a webserver issue myself because a couple months ago, everything seemed to be working fine. But the host keeps changing things in their infrastructure. Now IE just randomly times out and the number of graphics that the PDF can house is significantly less before the IE timeout. Nothing in the code has changed and the DB timeout in the config is the same.
How can I debug this scenario?