Had that problem on my Fatboy once. Look carefully at the key and make sure that the barrel is not cracked or deformed. Mine had a small crack in it and caused it to hang and I couldn't get it out.
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2013 FLTRU, Jackpot 2/1/2 Stainless Ceramic Coated Head Pipes, Fuelmoto Stage 1 Intake, Power Vision, Jackpot Full Size Ceramic Crossover, MADSTAD 16" Windshield, Motolight Running Lights, Nostalgic Rails, Airhawk R, Hayden Primary Tensioner, V&H Roland Sands Slant Slip-Ons