This cross-cultural study of the Philippines and the United States examines factors that affect students' online learning motivation by focusing on technical and psychological perceptions and how these perceptions influence goal orientation for online learning among American and Filipino students. Applying Self-Determination Theory and the Technology Acceptance Model as the theoretical foundations, this study scrutinizes how the two countries' different cultural perceptions and levels of IT infrastructure affect online learning. Several constructs for psychological and technological aspects were measured. All relationships were significant for both countries. However, external regulation is not significant to intrinsic motivation for the American respondents, while an external reward is negatively significant to intrinsic motivation for Filipino respondents. This study suggests that psychological and technological factors are important to increase intention to take online classes for American and Filipino students.