Hypofractionated stereotactic radiotherapy (HSRT) for patients with resected or large intact brain metastases is increasing in clinical practice; however, reporting on patterns of failure, specifically leptomeningeal disease (LMD) is lacking. In this study we identify patterns of LMD and determine predictors for developing LMD in patients with intact or resected brain metastases treated with 5-fraction HSRT. A single-institution retrospective review of a prospective database identified patients receiving HSRT for intact brain metastases or surgical cavities. Patient, tumor, and treatment factors were extracted. Patterns of LMD were stratified into four groups based on their radiographic presentation: focal classical, diffuse classical, focal nodular and diffuse nodular. Univariate and multivariable analyses were conducted to determine potential predictors for developing LMD. HSRT was delivered to 320 intracranial lesions (57% intact and 43% surgical cavities) in 235 patients with a median follow-up of 13.4 months (range, 0.8 to 60 months). The most common dose regimen was 30Gy in 5 fractions (65%). Overall, the incidence of developing LMD was 19% and the most common radiographic presentation of LMD was a diffuse nodular pattern (44%). The 6-month and 1-year rates of LMD were 7.5% and 12%, respectively. On multivariable analysis for the entire cohort, cavity lesions were statistically significant predictors of LMD compared with intact metastases (24% vs. 7%; hazard ratio=0.47; p=0.01). For cavities alone, radiosensitive tumors (including non-small cell lung, small cell and breast cancer) were the only statistically significant predictor of LMD (p=0.030), with a trend towards significance observed for increasing maximum tumor diameter (p=0.050). From the date of LMD diagnosis, the median overall survival (OS) for the entire cohort was 3.8 months (range, 0.2 to 20.8 months). The 6-month and 12-month OS rates were 42% and 15%, respectively. No statistically significant difference in OS was observed between the four patterns of LMD (p=0.203) or between nodular and classical patterns (p=0.267). For patients treated with HSRT, surgical cavities are at increased risk of developing LMD compared to intact brain metastases. Our findings suggest that despite the ability of HSRT to safely escalate tumor dose compared with single-fraction SRS, it may still be insufficient to mitigate the heightened risk of LMD observed with surgical cavities. Further research is required to determine optimal strategies to reduce LMD rates.