Objectives: This study compares objective measures of cognitive performance with subjective perception of specific performance on neuropsychological tests examining basic cognitive domains, including, for the first time, financial capacity. Additionally, differences in assessment between single- and multiple-domain aMCI, mild AD, and healthy elderly regarding insight are examined. Methods: Participants completed a number of neuropsychological tests and the Legal Capacity for Property Law Transactions Assessment Scale (LCPLTAS). After every test, participants were asked to complete the Clinical Insight Rating scale (CIR) and to self-evaluate their performance by comparing it to what they considered as average for people of their age and educational level. Results: These preliminary findings show significant differences in the self-assessment patterns of the four groups in measures of verbal memory, visuospatial perception and memory, executive functions, tests of attention, and financial capacity. Mild AD expressed the highest overestimations, followed by single- and multiple-domain aMCI as well as controls. Accuracy of self-report is not uniform across groups and functional areas. Conclusions: Unawareness of memory deficits in both MCI subtypes is contradictory to subjective memory complaints as being an important component for clinical diagnosis. Financial capacity is overestimated in MCI and mild AD, a finding that has a plethora of clinical and legal implications.