According to the World Health Organization (WHO), the estimated number of older adults is around 962 million and is projected to increase to 2.1 billion by 2050. The oral frailty concept is associated with gradual oral function loss in relation to aging. There is a need to emphasize the improvement of oral function based on an evaluation of masticatory performance in patients with various oral conditions or systemic diseases and especially in the frail elderly. The present narrative review presents an overview of the current state of the assessment and improvement of masticatory performance in frail older people. To fully encompass oral frailty, oro-facial hypofunction, or oro-facial fitness, dental Patient Reported Outcomes (dPROs) should be included; nevertheless, there are limited evidence-based rehabilitation approaches. The concept of oral frailty, oro-facial hypofunction, or oro-facial fitness should involve dental Patient Reported Outcomes (dPROs), and in this sense, there are only a few evidence-based rehabilitation procedures to improve oro-facial hypofunction besides prosthodontics. It must be considered that reduced neuroplastic capacity in old individuals might preclude a positive outcome of these strategies that might need to be accompanied by functional training and nutritional counseling.