(1) Self-regulation of driving is a means of maintaining one’s driving identity. The purpose of this study was to investigate the extent to which older drivers with Mild Cognitive Impairment (MCI) are metacognitively aware of the requirements of specific demanding driving conditions and whether this awareness is linked to subjective assessments of cognition. (2) One hundred seventeen (117) older MCI drivers participated in a telephone survey in which they reported their metacognitive experiences in nine driving conditions, listed as an aim of self-regulation. The analyses included the participants’ subjective cognitive assessments, both in terms of their cognitive state and their perceived driving self-efficacy. (3) The analyses pointed out a direct and negative effect of age on the formation of the metacognitive feeling of certainty. Furthermore, an indirect effect of sex through driving self-efficacy was established. This effect was negative in the case of the metacognitive feeling of difficulty and the estimation of effort and positive in the case of the metacognitive feeling of certainty. (4) This position points out the need to establish appropriate levels of the perceived self-efficacy of older drivers with MCI, and it raises issues when it moves to fictitious levels.