Anesthesiology residents' experiences and perspectives about their programs may be helpful in improving training. The goals of this repeated cross-sectional survey study are to determine: (1) the most important factors residents consider in choosing an anesthesiology residency, (2) the aspects of the clinical base year that best prepare residents for anesthesia clinical training, and what could be improved, (3) whether residents are satisfied with their anesthesiology residency and what their primary struggles are, and (4) whether residents believe their residency prepares them for proficiency in the 6 Accreditation Council for Graduate Medical Education (ACGME) Core Competencies and for independent practice. Anesthesiologists beginning their US residency training from 2013 to 2016 were invited to participate in anonymous, confidential, and voluntary self-administered online surveys. Resident cohort was defined by clinical anesthesia year 1, such that 9 survey administrations were included in this study-3 surveys for the 2013 and 2014 cohorts (clinical anesthesia years 1-3), 2 surveys for the 2015 cohort (clinical anesthesia years 1-2), and 1 survey for the 2016 cohort (clinical anesthesia year 1). The overall response rate was 36% (4707 responses to 12,929 invitations). On a 5-point Likert scale with 1 as "very unimportant" and 5 as "very important," quality of clinical experience (4.7-4.8 among the cohorts) and departmental commitment to education (4.3-4.5) were rated as the most important factors in anesthesiologists' choice of residency. Approximately 70% of first- and second-year residents agreed that their clinical base year prepared them well for anesthesiology residency, particularly clinical training experiences in critical care rotations, anesthesiology rotations, and surgery rotations/perioperative procedure management. Overall, residents were satisfied with their choice of anesthesiology specialty (4.4-4.5 on a 5-point scale among cohort-training levels) and their residency programs (4.0-4.1). The residency training experiences mostly met their expectations (3.8-4.0). Senior residents who reported any struggles highlighted academic more than interpersonal or technical difficulties. Senior residents generally agreed that the residency adequately prepared them for independent practice (4.1-4.4). Of the 6 ACGME Core Competencies, residents had the highest confidence in professionalism (4.7-4.9) and interpersonal and communication skills (4.6-4.8). Areas in residency that could be improved include the provision of an appropriate balance between education and service and allowance for sufficient time off to search and interview for a postresidency position. Anesthesiology residents in the United States indicated they most value quality of clinical training experiences and are generally satisfied with their choice of specialty and residency program.