This study aims to develop and test an amalgamated conceptual framework based on Technology Acceptance Model (TAM) and other models from social psychology, such as theory of reasoned action and TAM2 that captures the salient factors influencing the user adoption and acceptance of web-based learning systems. This framework has been applied to the study of higher educational institutions in the context of developing as well as developed countries (e.g. Lebanon and UK). Additionally, the framework investigates the moderating effect of Hofstedes four cultural dimensions at the individual level and a set of individual differences (age, gender, experience and educational level) on the key determinants that affect the behavioral intention to use e-learning. A total of 1197 questionnaires were received from students who were using web-based learning systems at higher educational institutions in Lebanon and the UK with opposite scores on cultural dimensions. Confirmatory Factor Analysis (CFA) was used to perform reliability and validity checks, and Structural Equation Modeling (SEM) in conjunction with multi-group analysis method was used to test the hypothesized conceptual model. Our findings suggest that individual, social, cultural and organizational factors are important to consider in explaining students behavioral intention and usage of e-learning environments. The findings of this research contribute to the literature by validating and supporting the applicability of our extended TAM in the Lebanese and British contexts and provide several prominent implications to both theory and practice on the individual, organizational and societal levels.