Hoarding Disorder (HD) is defined by the inability to discard objects until clutter becomes functionally impairing. A DSM-5 specifier for HD is lack of insight. A recent study found links between insight (using an objective clutter proxy) and inhibitory/cognitive control in HD. We aimed to explore associations between insight (using the same clutter proxy) and symptom severity, functioning, and cognition in Veterans with HD. 122 Veterans seeking treatment for HD completed pre-treatment assessments, including home-based assessments of clutter volume using the Clutter Imaging Rating Scale (CIR), HD severity measures, self-reported functioning, and neuropsychological testing. Insight was defined as the difference between the assessor and self-rating of the CIR (i.e., CIR-error). T-tests and regressions were used to evaluate the relationships between measures. The majority of the Veterans were older (m = 62), male (61 %), and White (57 %), with some college education. On clinical interview, only 10 % of the sample were rated with impaired insight. The mean CIR-error score was in the impaired range, with 47 % of the Veterans underreporting clutter. Lower HD severity and higher self-reported functioning were related to lower insight. Neuropsychological test performance was related to insight, but with small effects in varying directions. Nearly half of treatment-seeking Veterans demonstrated impairment in insight into levels of clutter, similar to previous work. Objective insight ratings demonstrated better sensitivity than clinician interviews for insight impairments. Lower insight was related to lower self-reported HD severity and higher self-reported functioning, raising the question of a potential insight paradox in HD.