Abstract Objective Given the potential risks associated with compromised judgment in older adulthood, we examined whether informant-reported practical judgment abilities were associated with cognitive impairment and measures of brain structure. Method 97 community-dwelling older adults with informants (Mage = 74.64 ± 7.42, Medu = 15.76 ± 2.42, 74%female, 92%white) underwent neuropsychological evaluation, including the Test of Practical Judgment-Informant (TOP-J-INF), a 15-item informant-reported scale of judgment ability. Participants were diagnosed with mild cognitive impairment (MCI; n = 33) or as neuropsychologically unimpaired (n = 64). Participants completed an MRI study including T1-weighted image processed with FreeSurfer software (v 6.0.0) to obtain estimates of gray matter volume and cortical thickness (parcellated with the Desikan-Killiany atlas). Logistic and linear models analyzed the association of TOP-J-INF with MCI diagnosis and brain volume/thickness (in separate models). To better support the exploratory nature of this analysis of associations with structural brain variables, we did not apply correction for multiple comparisons. Results Each additional point on the TOP-J-INF increased the odds of MCI diagnosis by 16.8% (OR = 1.168, p = 0.004). Worse judgment was associated with reduced brain volume in the right parahippocampal gyrus (β = −11.688, p = 0.032), superior temporal gyrus (β = −51.330, p = 0.040), rostral anterior cingulate cortex (β = −25.704, p = 0.004); and reduced thickness of the left transverse temporal gyrus (β = −0.010, p = 0.041). Conclusions To our knowledge, this is the first study to investigate the relationship between informant report of judgment and measures of brain structure, providing support that informant concerns about a loved one’s compromised judgment is associated with volume/thickness reduction in key brain regions. Assessing practical judgment abilities via informants could provide critical clinical information when working with vulnerable older individuals.