Background: The lack of a universal system for fracture healing progress evaluation recommended by evidence-based orthopedics is mentioned in current literature. Radiographs and the observation of clinical signs and symptoms remain standard practice for the assessment of fracture healing progress. Objectives: The general aim of this study was to show the main functionalities of the Web-based telediagnostic tools designed to improve fracture healing assessment follow-up and to present a study of fracture healing assessment based on collected study group of long bone fracture cases. Methods: The originally designed Web-based system was used to assess remotely fracture healing in 40 complete radiographic sets (211 radiographs) randomly selected from a database. Digital radiographic images and clinical data were stored in the database and then subjected to detailed analysis. Descriptive classifications, scorings, and radiographic image optical density analysis measurements were used for a series of cases. Results: Curves on the graph, drawn from the consecutive follow-up measurements of fracture gap optical density, can slope down regularly in normal healing cases or remain irregular and disorganized in delayed unions. An association between optical density values, callus index, and descriptive scoring variables was found for normal healing based on results received from Web-based telediagnostic system. Conclusions: The development of Web-based telediagnostic applications have the potential to improve fracture qualitative and quantitative evaluation and monitoring for the improvement of the quality of fracture care. The results imply the feasibility of Web-based fracture healing assessment telediagnostic applications over the Internet.