Ibrutinib is an oral Bruton tyrosine kinase inhibitor approved for use in patients with B-cell malignancies and has been shown to increase progression-free survival in patients with chronic lymphocytic leukemia (CLL). Ibrutinib is known to increase bleeding risk in patients with CLL. We report a patient with CLL on ibrutinib who experienced significant and prolonged bleeding after a routine superficial tangential shave biopsy for suspected squamous cell carcinoma. This prompted temporary cessation of this medication for the patient's subsequent Mohs surgery. This case demonstrates the possible severity of bleeding following routine dermatologic procedures. It is important to consider holding the medication prior to planned procedures such as dermatologic surgery.