Was Shawn able to access anything on the server that would confirm/deny that the image upload was coming through? Why did the image upload work in the test environment but not in the released version of the app? What was different about the test environment?
In theory, Shawn should have had enough access to the server environment (either by running the servers himself or asking someone to help him diagnose why an upload failed silently) that he should have had a reasonably quick answer to "why is this upload succeeding but not showing up?"
IMO, those lessons (why the upload worked in test but not in production) are significantly more important than "the image mime type was set to 'jpg' but should have been 'jpeg'" The bug is much more inconsequential to why the environment made it so hard to find the bug.
In my case, I had a situation where a desktop application was severely malfunctioning, but errors were not being logged. It took me multiple days to realize that the application was running out of file handles, and that log4net wouldn't log if it couldn't get a file handle. Even though the fix (reverting a very small bugfix) was simple; the real fix was to customize log4net to always keep the log file open. This way, if the application ran out of file handles, the error would be logged.