In recent years online innovations in Internet content offerings has produced a myriad of highly interactive fantasy sports and gambling sites designed to entice users to wage funds. Although factors such as accessibility and anonymity help motivate people to bet online, many hesitate to wager for reasons that must be examined if online betting websites (OBW) are to continue to innovate and grow. Our research examines how OBW users’ past experiences and perceived reputation influences psychological contract violation (PCV) and perceived institutional effectiveness as they pertain to OBW offerings. We also investigate the effect of institutional effectiveness on users’ concerns and betting behavioral intention. Initial results suggest that OBW users have concerns about transactional information even though they tend to be less risk adverse than non-OBW users. This study also found that psychological contract violation minimizes users’ perception about overall OBW structures’ effectiveness developed to protect online gamblers.