Many authentication schemes ask users to manually compare compact representations of cryptographic keys, known as fingerprints. If the fingerprints do not match, that may signal a man-in-the-middle attack. An adversary performing an attack may use a fingerprint that is similar to the target fingerprint, but not an exact match, to try to fool inattentive users. Fingerprint representations should thus be both usable and secure. We tested the usability and security of eight fingerprint representations under different configurations. In a 661-participant between-subjects experiment, participants compared fingerprints under realistic conditions and were subjected to a simulated attack. The best configuration allowed attacks to succeed 6% of the time; the worst 72%. We find the seemingly effective compare-and-select approach performs poorly for key fingerprints and that graphical fingerprint representations, while intuitive and fast, vary in performance. We identify some fingerprint representations as particularly promising.