It is well established that individuals with cognitive impairment present with disturbed forms of pain processing of still unknown origin. As a neurocognitive factor, executive functions have become favored candidates for explanation. For further insights, we aimed at comparing executive functions and memory in their association with parameters indicating onset and escalation of pain perception. Subjective ratings of experimentally induced pressure pain applied in ascending series were assessed in older individuals with (N = 32) and without mild cognitive impairments (MCI) (N = 32). We investigated whether executive functioning (Trail Making Test-B (TMT-B), semantic fluency) or memory (word list and figure recall) were more closely linked to the onset and the escalation of pain. For the MCI group, a strong linkage between pain responses and the TMT-B could be found, i.e., poor test performance was associated with weak pain onset but strong pain escalation. The contribution of memory functions was less substantial and systematic. The prominent role of executive function for pain processing in individuals with MCI could be replicated by a test of cognitive flexibility. This lack of adaptability let individuals with MCI be less vigilant to pain at the beginning but allows for escalating pain in the further course. Thus, being first not sufficiently prepared and later overwhelmed as regards pain may be an early problem in MCI individuals with reduced executive functioning