Aim/Purpose: This research investigates the success variables affecting the adoption of social networking sites (SNS), namely Facebook, and learning management systems (LMS), specifically Moodle, in developing countries. Background: In contemporary education, universities invest heavily in the integration of LMS with traditional classrooms. Conversely, such technologies face a high rate of failure and not all learners are satisfied with LMS services. In turn, this leads to the exploitation of SNS interactive features and services, which are subsequently included in the process of teaching and learning. However, the success of both SNS and LMS has rarely been studied in the context of developing nations. Methodology: In this study, a cross-sectional survey was used to collect the research data. It targeted a population sampled from amongst state-sector university undergraduates in Iraq (N=143). The study was based on an extension of DeLone and McLean's Information Systems Success (D&M ISS) model to include four antecedent variables: system quality, information quality, technology experience, and Internet experience as direct determinants of technology use and user satisfaction, both of which affect the net benefits of Facebook and Moodle. The collected data were analyzed with SmartPLS, using a partial least squares-structural equation model (PLS-SEM). Contribution: This research extends previous literature on the critical success factors (CSF) of SNS and LMS in the case of developing countries. The study guides the way in which the acceptance of SNS and LMS in higher education can be organized in the developing world in general, especially in the Middle East, thereby bridging this research gap and extending previous literature. Findings: The research results support the influence of quality and experience antecedents on technology use and learner satisfaction. The extended model also provides full support for the association between technology use and learner satisfaction, concerning the net benefits of Facebook and Moodle. The proposed model achieved a good fit and explained 61.4% and 68.1% of the variance of LMS and SNS success, respectively. Recommendations for Practitioners: The significant influence of the constructs investigated in this research could shape strategies and approaches to be adopted for the enhancement of SNS and LMS implementation in educational institutions. More specifically, this study is aimed at guiding SNS and LMS acceptance in developing countries, especially in Middle Eastern higher education. Recommendation for Researchers: This work offers a theoretical understanding of the body of knowledge on SNS and LMS application in institutes of higher education. It further supports the usefulness of the D&M ISS model for predicting the success of social networks and e-learning systems. Future Research: As with most empirical literature, this research makes a number of recommendations for further work. Future research could investigate other constructs that potentially influence technology success in education such as facilitating conditions, perceived privacy, and security. Moreover, researchers from different contexts are invited to apply this extended model and conduct a mixed methods (quantitative and qualitative) analysis to deepen the current understanding of the effect of SNS on teaching and learning, while also comparing it with the impact of LMS in this digital era.