An analysis of the problems pertaining to the adoption of a year-round calendar for high schools, along with the advantages of year-round education (YRE), are examined. It provides a literary review (including historical contexts), types of calendars, benefits, administrative problems, and societal benefits. For the study, 28 schools responded to a questionnaire sent to 40 year-round high schools throughout the United States. The results indicate that the single-track, year-round calendar can be found in high schools of all sizes, in both rural and urban areas. The most common problems were those dealing with athletics, teacher-training opportunities, and building maintenance. Athletic concerns included additional compensation to coaches for maintaining offseason programs and remaining within the guidelines of the athletic governing agencies. However, not every school reported administrative concerns, and none of the schools consistently reported the same types of problems. Furthermore, universities have tried to be flexible in offering teacher training, and maintenance schedules can be adapted for YRE. Suggestions as to how schools can meet challenges produced by YRE are offered. Appendices include the study questionnaire, guidelines, and sample calendars. (RJM)