Am I correct to assume that automatically redownloading a JNLP application does not occur when the last modified time for the Jar resource on the server is older than the one that IcedTeaWeb (OpenJDK) has cached? What is the recommended way to support downgrading a JNLP application then without forcing the user to clear the cache?
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yes. The cache implementation uses a HEAD request to see if there is a newer version. If the response of the HEAD request shows that the last modified date is older than the cache date no GET request is sent to the server.

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