To Mark:
I'll try running it from the command line, and seeing what happens. With regards to the JRE version, I am running Sun code, but it's not quite standard. Apple take the source code from Sun, and then create their own implementation of Java specifically for MacOS. As of right now, Apple Java is the equivalent of JRE 1.4.2_05 from Sun.
From what I understand, the core of Java remains the same, but Apple 'Aquatise' the UI experience so it better blends with native MacOSX applications. Looking at the stack trace from the JVM, it could well be this Apple code that has the problem. Ideally, I'd like to get a core dump from the JVM, but I'm not sure how to force MacOSX to generate them. If anyone knows, please drop me a line.
To Tony:
You can always workaround the problem by making sure that your uploads are less than this size. It's just annoying, as I have to do the uploads in several batches. As I've just re-uploaded about 50GB of music, it was a bit painful.
Andy.