The direction of the task-unrelated thought (TUT)-task difficulty relationship varies depending on the type of task used, which can be challenging for extant theories to explain. Individual differences in cognitive ability and motivation, and distinctions of intentional and unintentional TUTs have increased our ability to account for these inconsistencies. Recently, research has also suggested a role for subjective appraisals of task difficulty influencing TUTs. As such, the present study aims to observe the integrated roles of cognitive and motivational variables and subjective appraisals in explaining between task differences of two commonly applied paradigms in the literature (i.e., sustained attention and working memory paradigms). Experiments 1 (N = 100) and 2 (N = 104) measured individual differences in top-down appraisals (perceived difficulty, motivation, and interest) and working memory, as well as the type and frequency of TUTs during a sustained attention to response task (SART) and n-back task (1-back and 3-back). Results confirmed a curvilinear relationship between TUTs and difficulty across these tasks, with intentional and unintentional TUTs most frequent during the SART ("easy" task) and 3-back ("difficult" task), respectively. Furthermore, Experiment 2 included a modified SART with a changing-target identity that demonstrated influences of both objective and subjective difficulty and task characteristics on intentional TUT rates. Collectively, these experiments demonstrate the separable as well as integrated roles of cognitive-motivational variables and subjective appraisal in determining intentional and unintentional TUTs during different types of tasks.