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I assume you're updating the version number? (e.g. 2.2 to 2.3)
When you view the javaws resources (particularly the jnlp file in your case) in the control panel ("javaws -viewer" in command prompt will launch panel, click "view" on the general tab) do they show an entry in the "expired" column?
If you are not setting the expires header when returning the file from the server javaws is perhaps assuming the old jnlp is still valid?