Follicular Occlusion Syndromes (FOS) are rare chronic relapsing skin disorders characterized by abnormal follicular hyperkeratinization, plugging, and inflammation. FOS are more commonly discussed as a ‘triad’ or ‘tetrad’ based on the patient’s clinical presentation. The triad includes hidradenitis suppurativa, acne conglobata, and dissecting cellulitis of the scalp. The tetrad in addition to the triad includes a history of pilonidal cysts. These disorders have a considerably negative effect on quality of life due to chronic pain, psychological distress, and body image concerns. Delayed or misdiagnosis can exacerbate patient outcomes, heightening the importance of timely identification and multidisciplinary treatment. We present two previously unrecognized cases of FOS to raise awareness to improve management.