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A term used as a warning of predicted impending failure. [Generally] the phrase relates to any situation where the outcome has been perceived as unlikey to gather the desired result (Fail) and yet still that course of action is chosen anyway due to either [ignorance], arrogance or both. The term is also known as "boarding the failboat". A Failboat [representing] the action/activity that is deemed to likely end in a Fail. Noobs tend to be the captains of such vessels.
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