Background: Guidelines regarding injury prevention in fast-pitch softball pitchers have yet to be widely adopted, risking the online dissemination of misleading advice. Purpose/Hypothesis: The purpose of this study was to assess the source and medical advisability of online pitching recommendations for youth softball players and highlight the risk of misinformation. It was hypothesized that many popular websites would contain content discordant with current medical guidelines regarding windmill softball pitching recommendations. Study Design: Cross-sectional study. Methods: A Google search using the phrase “youth softball pitching recommendations” was performed. Up to 100 websites were extracted and analyzed for website source type (commercial, medical/educational, or athletic organization) and informational quality (advisable, neutral, or discordant). The latter was determined with respect to the STOP Sports Injuries guidelines for arm injury prevention in youth softball players. Descriptive and inferential statistics were used to assess potential associations between website source type and the informational quality of content therein. Results: A total of 86 websites were included in the analysis. Website source type was significantly predictive of informational quality ( P = .018). Among the 3 source types, medical/educational websites had the highest proportion classified as advisable (12/24 [50.0%]) and the lowest proportion classified as discordant (3/24 [12.5%]). Only 17.6% (6/34) of commercial websites were advisable, and advisable websites as a whole were more likely to be from medical/educational sources than athletic organization ( P = .016) or commercial ( P = .026) sources. The advisability rate among all websites was 25.6% (22/86). Although there was a significant association between position in the search results (first 10 vs remaining 76) and website source type ( P = .006), there was no association between position and informational quality ( P = .116). The first 10 websites, which trended toward greater advisability than the remaining 76 websites ( P = .060), were more likely than the remaining websites to be medical/educational sources ( P = .002). Conclusion: Website source type was significantly predictive of medical advisability. Medical/educational websites were the most advisable, while commercial and athletic organization websites were especially poor in their advisability. The overall advisability rate was only 25.6%. When making recommendations to patients, sports medicine providers should highlight the prevalence of discordant online softball pitching guidelines and take the opportunity to share medically advisable resources.