We report two cases of tendon rupture associated with ciprofloxacin. One patient had a complete rupture of an Achilles tendon 6 months after taking the medication. The other case involved a partial rupture of the subscapularis tendon. Both ruptures occurred with minimal mechanical stress on the tendons, suggesting that the fluoroquinolone increased the susceptibility to rupture. We also review the literature describing the association between fluoroquinolones and tendon rupture and discuss the mechanisms explaining the heightened risk of tendon rupture associated with these drugs.