Background: Significant distal interphalangeal joint (DIPJ) pathology can occur with few radiographic findings but can be accompanied by joint capsule enthesopathy on the middle phalanx. Objectives: To explore the associations and correlations between DIPJ capsule enthesopathy identified radiographically and DIPJ articular cartilage abnormalities and other concurrent soft tissue or osseous pathology within the foot found on MRI. Study Design: Retrospective and descriptive case series. Methods: Cases identified with DIPJ capsule enthesopathy were retrospectively reviewed. Abnormalities were graded using a 4-point scale. Descriptive statistics and Spearman’s rank correlations were used to analyze the relationship between the presence and grade of DIPJ capsule enthesopathy, lameness, and DIPJ intra- and extra-articular abnormalities. Results: Twenty-one MRI scans and radiographs with DIPJ capsule enthesopathy were analyzed. DIPJ articular cartilage lesions were identified in 20/21 limbs (95%). There was no significant correlation between the degree of DIPJ capsule enthesopathy and severity of articular cartilage lesions. DIPJ proliferative synovitis and osteophytes were present in majority of limbs (91% and 95%), respectively. DIPJ collateral ligaments were abnormal in 52% of the limbs. DIPJ capsule enthesopathy grade was moderately positively correlated with DIPJ collateral ligaments’ findings severity (p=0.01). Main Limitations: Retrospective character, no histopathology, studied cases limited to one referral center. Conclusions: The presence of DIPJ capsule enthesopathy on radiographs is a reliable finding to rule in DIPJ damage and support further case management, particularly in cases where advanced imaging is unavailable or desired.