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There is a cool workshop at Deepsec in Vienna mid of November, which is called "Defend the Flag". The idea is that you will be trained for a day and during the second day, you have to configure your systems and they will be attacked. The one that holds the longest wins. If you are interested, my colleague Gerhard Göschl blogged on it: Deepsec: Hacker Konferenz in Wien – Einladung zu kostenlosem Workshop "TechNet Briefing Spezial > Security"