This study set out to examine an integrative model in which teacher learning climate is associated with teachers’ sense of work engagement, organizational commitment, and subjective well-being, via teacher job satisfaction as a mediator. Moreover, we assert that learning climate and job satisfaction impact student school engagement, thereby giving further validity to the importance of this subject in the educational system. Data were collected from a sample of 273 teachers and 1040 students from 23 elementary and high schools in Israel. As predicted, a multilevel mediation analysis reflected the positive indirect relationship between teacher learning climate and teachers’ sense of work engagement, organizational commitment, and subjective well-being), which was mediated by teacher job satisfaction. In addition, the crossover process between teachers and their students was also confirmed, proving that teacher job satisfaction is a mediator in the positive relationship between teacher learning climate and student school engagement. The discussion highlights the role of teacher learning climate in promoting positive schooling outcomes among teachers as well as students.