This study presents a conceptual model to investigate the e-health readiness required by healthcare organization and the impact of such readiness in enhancing e-health transformation success, and how the entrepreneurial alertness associated with e-health readiness. A scale to measure e-health readiness was developed and validated; then it being tested to collect the large-scale survey data from hospitals¡¦ top management team members. The partial least squares (PLS) method was empirically used to test the conceptual model and hypotheses through the large-scale survey collected. The empirical results support the proposed model. The analysis not only provides the evidence that the effect of entrepreneurial alertness on e-health readiness is direct also showing e-health readiness has a positive effect on e-health transformation success. The results advance the understanding what determining factors of the e-health transformation success and also can potentially be used in advance of e-health transformation for contemporary hospitals to check its e-health readiness level and prepare the needed changes for e-health implementations to ensure better e-health transformation.