Purpose: To objectively and subjectively evaluate eye drop technique and assess communicated instructions, and reported problems with eye drop instillation among tertiary care sample eye drop users. Methods: A cross-sectional, observational study was carried out among patients attending our outpatient clinic from June to September 2020. Eligible participants obtained through convenient sampling were assessed for their eye drop instillation performance. The objective evaluation was made using observation of a demonstration and subjective assessment through responses to an interview. Patient inclusion criteria were being aged ≥18 years and using eye drops for ≥ one month; excluded if having a disability in communication or physical barriers in using eye drops. The patient reported difficulties and previous education about the instillation were also obtained. Results: Participants ( n = 84) had a mean age of 50.3 ± 14.0 years. During the demonstration, almost everyone (86.9%) successfully instilled at least one drop in the eye. None of the participants exhibited a perfect drop technique. The most common deviations were failing to close the eye (60.7%), touching the bottle to the eye or eyelid (36.9% of patients), and multiple blinks after drop instillation without nasolacrimal occlusion (25.0%). Forty percent of patients reported ≥1 problem and only a small sample recalled having had education in the eye drop instillation technique. Conclusion: Most participants failed to properly execute the eye drop technique. A proactive role of the prescribing practitioner to assess a patient’s ability to instill eye drops correctly could be helpful.