Although a key objective of Internet gambling service providers is player retention, there is a concomitant need to reduce the social costs of gambling. Our study shows how habit and prospect theories help build an integrative framework for decision support in regulated Internet gambling environments. To illustrate the practical implication of this framework, we applied the Cox model with time-dependent covariates on real gambling data collected from 4,222 users of a gambling website. The results help establish the positive association of key indicators such as the prior outcomes on the activity lifespan of an Internet gambler and the moderating effect of gambling frequency on the positive association between prior outcomes and gambling lifespan. This research is expected to contribute to the literatures on IT adoption and diffusion in general, and IT-based addictive behavior in particular.