When it comes to paying taxes, nobody wants to pay any more than they have to. But some taxes just seem patently unfair on their face, designed to take advantage of those least able to pay them.

In the following video, Dan Caplinger, The Motley Fool's director of investment planning, looks at what might be the most surprising tax anyone ever has to pay. Dan notes that those who receive unemployment insurance benefits are often surprised to find out that those benefits are subject to federal income tax. Dan points out that given their function of providing minimal income support to recipients, taxing unemployment benefits seems contrary to public policy. Yet he also notes that the idea makes some sense, as unemployment benefits are designed to replace wages, so treating them like wages has some justification. Dan concludes by noting that some states are smart enough to make unemployment benefits exempt from state income tax, but for the federal government, recipients don't have much choice.

Be smart about your taxes for 2014
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Fool contributor Dan Caplinger has no position in any stocks mentioned. The Motley Fool has no position in any of the stocks mentioned. Try any of our Foolish newsletter services free for 30 days. We Fools may not all hold the same opinions, but we all believe that considering a diverse range of insights makes us better investors. The Motley Fool has a disclosure policy.