This depends on the plugin, not all plugins are compatible with even a minor JIRA upgrade, so it has happened to us that plugins that were licensed in JIRA 4 worked in JIRA 5.x but could not be upgraded due to having to repurchase (paid updates) for a new license and once we moved to 6.2.1 the were no longer working. If it's a critical plugin i would suggest paying for it or start thinking of how to work without it.
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