How do task experiences support proximal and longer-term desires to reengage? Central to this question is the interplay between perceptions of task difficulty and the situational interest. This interplay is increasingly researched but not yet well understood. Micro-analytic, latent studies are important tools for replicating past findings and extending our understanding in this area. This study aimed to extend our understanding of the interplay between readiness (prior knowledge and individual interest), a sequence of mathematics task experiences (situational interest and perceived difficulty) and reengagement beyond the set of tasks (i.e. optional follow-up engagement). Participants (ages 20-49; n = 301) completed a series of maths tasks online, self-reporting their task experiences after each task. Participants were offered an optional opportunity to follow-up with the task content as a measure of their continued interest. Both readiness components assessed were important predictors of future situational interest (positive) and perceptions of task difficulty (negative). Persistent interconnections between the task experience components across time supported past evidence regarding the important role of situational interest and the challenges of perceived difficulty for sustained engagement. Modelling indicated that task success ([beta] = 0.36), situational interest ([beta] = 0.16) and perceptions of task difficulty ([beta] = 0.21) can converge on choices to reengage with an object going forward.