Systems and methods for inspecting wound optical fiber to detect and characterize defects are disclosed. The method includes illuminating the wound optical fiber with light from a light source and capturing a digital image based on measurement light that is redirected by the wound optical fiber to a digital camera. The method also includes processing the digital image with a computer to detect and characterize the defects. The types of defects that can be detected using the systems and methods disclosed herein include bubbles, abrasions, punctures, scratches, surface contamination, winding errors, periodic dimensional errors, aperiodic dimensional errors and dents.