Educational psychologists have researched the generality and specificity of metacognitive monitoring in the context of college-level multiple-choice tests, but fairly little is known as to how learners monitor their performance on more complex academic tasks. Even lesser is known about how monitoring proficiencies such as discrimination and bias might be related to key self-regulatory processes associated with task understanding. This quantitative study explores the relationship between monitoring proficiencies and task understanding in 39 adult learners tackling ill-structured writing tasks for a graduate “theories of e-learning” course. Using learner as unit of analysis, the generality of monitoring is confirmed through intra-measure correlation analyses while facets of its specificity stand out due to the absence of inter-measure correlations. Unsurprisingly, learner-based correlational and repeated measures analyses did not reveal how monitoring proficiencies and task understanding might be related. However, using essay as unit of analysis, ordinal and multinomial regressions reveal how monitoring influences different levels of task understanding. Results are interpreted not only in light of novel procedures undertaken in calculating performance prediction capability but also in the application of essay-based, intra-sample statistical analysis that reveal heretofore unseen relationships between academic self-regulatory constructs.