A dramatic perceptual asymmetry occurs when handwritten words are rotated 90 ° in either direction. Those rotated in a direction consistent with their natural tilt (typically clockwise) become much more difficult to recognize, relative to those rotated in the opposite direction. In Experiment 1, we compared computer-printed and handwritten words, all equated for degrees of leftward and rightward tilt, and verified the phenomenon: The effect of rotation was far larger for cursive words, especially when they were rotated in a tilt-consistent direction. In Experiment 2, we replicated this pattern with all items being presented in visual noise. In both experiments, word frequency effects were larger for computer-printed words and did not interact with rotation. The results suggest that handwritten word perception requires greater configural processing, relative to computer print, because handwritten letters are variable and ambiguous. When words are rotated, configural processing suffers, particularly when rotation exaggerates the natural tilt. Our account is similar to theories of the "Thatcher illusion," wherein face inversion disrupts holistic processing. Together, the findings suggest that configural, word-level processing automatically increases when people read handwriting, as letter-level processing becomes less reliable.