The present study investigated (1) the impact of cognitive styles on learner performance in well-structured and ill-structured learning, and (2) scaffolding as a cognitive tool to improve learners' cognitive abilities, especially field dependent (FD) learners' ability to thrive in an ill-structured learning environment. Two experiments were conducted with 116 college students recruited from a large research I university in the west of the United States. Experiment 1 (n = 42) employed the group learning strategy to match learners' cognitive styles in asynchronous online learning. The results showed that the style matching strategy failed to yield expected gains in ill-structured asynchronous learning for FD learners. Different from the style-matching strategy, experiment 2 (n = 74) used a scaffolding model proposed by Cazden (1988) to improve FD learners' cognitive abilities in asynchronous online learning. Results indicated that focusing on learners' cognitive abilities proved to be more effective than style-matching strategy for FD learners in both ill-structured and well-structured asynchronous online learning. Implications of the findings were discussed with suggestions for future research. (Contains 2 figures and 6 tables.)