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Exception in thread "extensionReloader" java.lang.NullPointerException
at it.gotoandplay.smartfoxserver.extensions.ExtensionManager.automagicReload(ExtensionManager.java:323)
at it.gotoandplay.smartfoxserver.lib.ExtensionAutoReloader.run(ExtensionAutoReloader.java:40)
at java.lang.Thread.run(Unknown Source)

Any ideas what could cause this?

Although I do know that I'm not cleaning up my extensions properly on destroy, but perhaps there is something else too.

quite strange, you'd better double check that you're not raising the exception in the destroy() method of your extension