The lower one-third of the leg, ankle, and posterior heel are devoid of robust soft tissue coverage. Coverage of exposed tendons, hardware, and bone can be challenging. The distally based medial hemisoleus flap is a viable option for soft tissue coverage. The medial hemisoleus flap is supplied by perforators from the posterior tibial artery. Complications of the flap are low, ranging around 8-20%; the most common complication is partial necrosis due to venous congestion. Patients with comorbidities are more prone to partial or complete flap loss and subsequent major amputation. The purpose of this study is to present a case series of medial hemisoleus flaps in high-risk patients with follow-up of 40-52 weeks. We present a case series of five multi-comorbid patients that underwent treatment of osteomyelitis for posterior heel wounds or chronic ankle wounds due to Charcot deformity. Patients were treated with surgical debridement, pathogen directed parenteral antibiotic therapy if indicated, deformity correction, if applicable, and distally based medial hemisoleus flap coverage of wounds. In contrast to free flaps, it allows for shorter operating time and does not necessitate microsurgical experience. The flap has a relatively low complication rate in the literature. In the setting of venous congestion and partial flap necrosis, this can often be managed with various techniques to prevent total flap loss. At follow-up of at least 40 weeks, the medial hemisoleus is a reliable procedure for soft tissue coverage of the lower leg, ankle, and posterior heel.