Objective: Measure perceived involvement in medical decision making and determine if anticipatory grief is associated with problem solving among family caregivers of older adults with cognitive impairment. Method: Retrospective analysis of baseline data from a caregiver intervention (n = 73). Multivariable regression models testing the association between caregivers’ anticipatory grief, measured by the Anticipatory Grief Scale (AGS), with problem-solving abilities, measured by the Social Problem Solving Inventory-Revised: Short Form (SPSI-R: S). Results: 47/73 (64%) of caregivers reported involvement in medical decision making. Mean AGS was 70.1 (± 14.8) and mean SPSI-R: S was 107.2 (± 11.6). Higher AGS scores were associated with lower positive problem orientation (p = .041) and higher negative problem orientation scores (p = .001) but not other components of problem solving—rational problem solving, avoidance style, and impulsivity/carelessness style. Discussion: Higher anticipatory grief among family caregivers impaired problem solving, which could have negative consequences for their medical decision making responsibilities.