Similarity between tasks is an understudied factor in research on cognitive flexibility. This behavioural experiment had 31 participants perform a task switch paradigm in which participants were required to switch between 4 tasks of varying similarity. The experiment was constructed in a way that simultaneously allows for investigating the impact of mental fatigue and task-rule congruency on the participants. The results indicate that similarity between tasks substantially impacts performance with different effects on RT and accuracy. While learning effects may have negated the impact of mental fatigue across the 5 experimental blocks, a significant decrease in performance was observed within blocks. Furthermore, the exploratory analysis proposes a novel interaction between task-rule incongruent trials and the task of the previous trial. These results support the notion that neither the interference view of cognitive flexibility nor the reconfiguration view are fully adequate at explaining task switch costs if similarity is added as a factor. The presented study presents strong evidence that fundamental findings in the domain of cognitive flexibility may not map linearly to more ecological settings where tasks are often more dissimilar.