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Whenever you execute the ant run command to run Wookie in standalone (developer) mode, the database is recreated. This means that if you stop and re-run Wookie you'll get an error message. To avoid this problem use ant clean-db run instead.

Why can't I add any widgets, either through the admin interface or by dropping them into the deploy folder?

One of the most common reasons for this is that the application doesn't have permission to write to the wookie/wservices directory, which is where Wookie expands widgets when they are uploaded. For example, if you are deploying Wookie on Tomcat, make sure webapps/wookie is owned by the tomcat user and not by root.