Background: Mobile phone messaging software robots allow clinicians and healthcare systems to communicate with patients without the need for human intervention. The purpose of this study was to (1) describe a method for communicating with patients postoperatively outside of the traditional healthcare setting by utilizing an automated software and mobile phone messaging platform and to (2) evaluate the first week of postoperative pain and opioid use after common ambulatory hand surgery procedures. Materials and Methods: The investigation was a prospective, multicenter investigation of patient-reported pain and opioid usage after ambulatory hand surgery. Inclusion criteria included any adult with a mobile phone capable of text messaging, who was undergoing a common ambulatory hand surgical procedure at one of three tertiary care institutions. Participants received daily, automated text messages inquiring about their pain level and how many tablets of prescription pain medication they had taken in the past 24 h. Initial 1-week response rate was assessed and compared between different patient demographics. Patient-reported pain and opioid use were also quantified for the first postoperative week. Statistical significance was set as p < 0.05. Results: Forty-seven (n = 47) patients were enrolled in this investigation. Total response rate of both pain and opioid medication questions through 7 days was 88.3%. Pain trended down on a daily basis for the first postoperative week, with the highest levels of pain being reported in the first 48 h after surgery. Patients reported an average use of 15.9 ± 14.8 tablets of prescription opioid pain medication. Conclusions: We find that a mobile phone messaging software robot allows for effective data collection of postoperative pain and pain medication use. Patients undergoing common ambulatory hand procedures utilized an average of 16 tablets of opioid medication in the first postoperative week.