Minimally invasive glaucoma surgery (MIGS) is a subset of glaucoma surgery that is known for its low rate of complications both intraoperatively and postoperatively compared to traditional filtering surgery. We present a case of a patient who, after receiving uncomplicated cataract extraction with posterior chamber intraocular lens implantation and concurrent iStent trabecular bypass stent implantation, experienced recurrent episodes of spontaneous microhyphema and inflammation in the late postoperative period. The patient, who had a history of mild asymmetric exfoliative glaucoma but no identifiable sources of trauma, underwent extensive examination to investigate causes of his episodic anterior segment bleeding and mild inflammation with concurrent elevated intraocular pressure. Given the circumstances of the patient's recurrent symptoms and a negative workup for conventional causes of recurrent hyphema, it was suspected that the patient's iStent was interacting with the patient's peripheral iris, causing microtrauma and hyphema. We hypothesized that this contact was potentially exacerbated by pre-existing exfoliation syndrome, which caused zonular weakness and subsequent anterior movement of the lens-iris diaphragm. After the patient's third recurrence of microhyphema and inflammation, the patient underwent removal of iStent and concurrent OMNI canaloplasty for glaucoma. Six months post-iStent explantation, the patient has had complete resolution of symptoms without recurrence of hyphema. In this case report, we outline the course of this patient's symptoms and diagnosis, discuss the potential of MIGS devices such as iStent to cause recurrent hyphema, and explore treatment options following removal.