Individuals with glaucoma are routinely prescribed and required to self-administer eye drop-based medication multiple times a day. Unfortunately, the process of self-administering eye drops requires a level of dexterity, strength, and visual acuity that the elderly population often do not possess, resulting in poor adherence and worsening condition. In this paper, we detail a prototyped eye drop assist device designed to safely and reliably deliver prescription medications. The ergonomic device safely anchors the eye drop bottle tip an optimal distance away from the face, aligns to the pupil, and provides feedback to the user when their head is at an appropriate tilt for a successful eye drop administration. We experimentally verify that the device improves hand steadiness, provides accurate head tilt feedback, precisely positions the bottle tip, and predictably delivers eye drops into the eye according to a parameterized model.