Children with mathematical difficulties need to spend more time than typically achieving children on solving even simple equations. Since these tasks already require a larger share of their cognitive resources, additional demands imposed by the need to switch between tasks may lead to a greater decline of performance in children with mathematical difficulties. We explored differential task switch costs with respect to switching between addition versus subtraction with a tablet-based arithmetic verification task and additional standardized tests in German elementary school children in Grades 1 to 4. Two independent studies were conducted. In Study 1, we assessed the validity of a newly constructed tablet-based arithmetic verification task in a controlled classroom-setting (n = 165). Then, effects of switching between different types of arithmetic operations on accuracy and response latency were analyzed through generalized linear mixed models in an online-based testing (Study 2; n = 3,409). Children with mathematical difficulties needed more time and worked less accurately overall. They also exhibited a stronger performance decline when working in a task-switching condition, when working on subtraction (vs. addition) items and in operations with two-digit (vs. one-digit) operations. These results underline the value of process data in the context of assessing mathematical difficulties.