Purpose: Homeless persons represent a vulnerable population with many barriers to healthcare and medication adherence which may be complicated by low health literacy. Medication adherence among homeless persons could be optimized through increasing the ease and convenience at which patients can receive medication counseling. In this study, a Skype service was utilized for prescription counseling purposes as an attempt to enhance the ease in which patients can speak with their pharmacist. Methods: This study involved an independent pharmacy that fills prescriptions for two homeless shelters. Upon prescription delivery, private medication counseling was offered to each patient by shelter personnel. Participation was voluntary. Counseling was provided by a pharmacist via Skype, utilizing video calls. Once the call was complete, patients were asked to fill out an anonymous survey consisting of eight true/false questions that assessed their perception of benefit of the service. Results: From January 2013 until March 2013, 47 surveys were completed. Results demonstrate that the Skype service was largely beneficial for those who participated, with 91.5% of the patients reporting they would use the service again. 100% of the patients reported they learned something about their medicine, 91.5% reported that seeing the pharmacist made them feel more comfortable, and 87.2% reported they did not have as many concerns about taking their medicine after speaking with the pharmacist. Conclusions: Implementing a Skype service in shelters to provide patients with convenient access to their pharmacist can help diminish some of the barriers to medication adherence that exist among homeless persons.