The study aims at assessing the reality of secondary education in Jordan from the high school principals' perspective, in addition to figuring out the impact of the gender differences on the results. To answer the study questions; the researcher selected the study sample using the stratified random method. The sample consisted of 73 headmaster and headmistress of secondary school from the southern governorates of Jordan (Ma'an, Al Shoubak, Petra, Southern Badia, and Aqaba) for the academic year 2017/2018. The researcher developed a questionnaire consisted of (35) paragraphs, divided into five fields: (building and equipment, students, teaching staff, curricula and educational supervision) and for the combined fields as well. The results of the study revealed the following: (1) Principals' assessment of the two fields of building and equipment, and students, and for the fields combined was high (2) Principals' assessment of teaching staff, curricula, and educational supervision was medium (3) Principals' assessment of the questionnaire was not affected by the gender.