This study furthers research in three crucial related areas: (1) comparing various online glossing and vocabulary learning tools; (2) language teaching and learning using a more natural bilingualized approach to developing online reading skills in a second or foreign language; and (3) comparing the relative level of enjoyment and effectiveness students experience when using various CALL programs. This paper applies recent insights into vocabulary learning behaviors and functions online and investigates whether teachers can help learners increase their use of online glosses to improve their vocabulary learning by giving them automatic mouse-over instant glosses versus optional, clickable, mechanical access. The authors compare Japanese college students' actual use of three types of glossing when reading similar texts online. The findings suggest that an expanded glossing system that helps encourage deeper lexical processing by providing automatic, archivable glosses would be superior for digital vocabulary learning because it can simultaneously offer better monitoring and more motivation vis-à-vis online word learning.