Engaging in cognitive activities early and regularly has been shown to improve cognitive performance and delay the natural progression of cognitive decline for older adults. Many factors can make it difficult to achieve this, such as lack of engagement, highlighting the potential for technology to enhance engagement with cognitive activities. This paper investigates the unique combination of haptic feedback and a Socially Assistive Robot (SAR) during categorization-based activities. In this experiment, passive and active kinesthetic force feedback led to improvements in factors such as usability and affective state compared to non-contact cutaneous (ultrasonic) feedback. The robot facilitation positively impacted older adults’ performance and their perception of usability and interactivity compared to using a laptop. Some design considerations emerged including the themes of control and informativeness of haptic feedback and the proxemics of the robot. This work supports the combination of haptic feedback, specifically force feedback, along with a SAR to foster engagement with cognitive activities for older adults.