The Alzheimer’s Association’s Memories in the Making® (MIM) art activity program is intended to enhance the well-being of individuals who are living with dementia. Previous evaluations of MIM have found that participants show benefits on several well-being domains measured by the Greater Cincinnati Chapter Well-Being Observation Tool^©. The current study extended those findings by looking for evidence of carry-over effects beyond the temporal boundaries of MIM sessions. Additionally, this study evaluated key psychometric qualities of the assessment instrument. Seventy-six MIM participants with middle- to late-stage dementia were evaluated by interns and care facility staff at the beginning, middle and end of a 12-week MIM program. Interns focused on behavior within MIM sessions and staff rated functioning outside MIM sessions. Staff reported no significant changes in resident well-being across the 12-week program. Interns reported significant improvements from the beginning to middle and end of the program on five well-being domains. Psychometric analyses of the Greater Cincinnati Chapter Well-Being Observation Tool^© identified weaknesses in inter-rater reliability and found that the instrument measures two orthogonal factors – interpreted as ‘Well-Being’ and ‘Ill-Being’ – not the seven domains claimed. Quantitative evidence for the effectiveness of MIM is ambiguous, but anecdotal observations indicate that the program is beneficial for some participants, if only fleetingly.