IMPORTANCE: Residency applicants often use social media to discuss the positive and negative features of prospective training programs. An examination of the content discussed by applicants could provide guidance for how medical education faculty can better engage with prospective trainees and adapt to meet the educational expectations of a new generation of digital-native physicians. OBJECTIVE: To identify unstructured social media data submitted by residency applicants and categorize positive and negative statements to determine key themes DESIGN: Qualitative analysis of a retrospective cohort SETTING: Publically available data sets PARTICIPANTS: Anonymized medical trainees applying to residency training positions in nine specialties: dermatology, general surgery, internal medicine, obstetrics/gynecology, plastic surgery, otolaryngology, physical medicine and rehabilitation, pediatrics, and radiology from 2007 to 2017. MAIN OUTCOMES AND MEASURES: After development of a standardized coding scheme which broke comments down into major features, themes, and subthemes, all unstructured comments were coded by two independent researchers. Positive and negative comments were coded separately. Frequency counts and percentages were recorded for each identified feature, theme, and subtheme. The percent positive and negative comments by specialty were also calculated. RESULTS: 6314 comments were identified with 4541 positive and 1773 negative entries. Institution was the most commonly cited major feature in both the positive (n=767, 17%) and negative (n=827, 47%) comments, with geography the most cited theme and city, cost of living, and commute commonly cited subthemes. Training was the next most cited major feature in both positive (n=1005, 22%) and negative (n=291, 16%) comments with clinical training more commonly cited compared to research opportunities. Overall, 72% of comments from all were positive; however, percent of comments that were positive comments varied significantly across the nine specialties. Pediatrics (65%), dermatology (66%) and internal medicine (68%) applicants were more likely to express negative comments compared to the global average while PM&R (85%), radiology (82%), ENT (81%), and plastic surgery (80%) were more likely to express positive comments. CONCLUSIONS AND RELEVANCE: This qualitative analysis of positive and negative themes as posted by applicants in recent matching years is the first provides new detailed insight into the motivations and desires of trainees.