A friend of his in New Orleans would forward his stories to publishers, so they had no idea the writer was imprisoned.
Med bivanjem v zaporu je pod različnimi psevdonimi objavil 14 zgodb, posebej poznan je postajal pod psevdonimom O. Henry, s katerim se je prvič podpisal pod zgodbo "Whistling Dick's Christmas Stocking", ki je izšla decembra 1899 v reviji "McClure's Magazine".