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The pesantren tradition has its internal ability to adapt and transform in the very strong and fast flow of social change. This tradition becomes a very important intellectual asset to be transformed into the present and future context. The process of transmitting and reproducing Islamic values and knowledge with prominent pesantren characters, namely: relies on the kyai figure, originates from al-kutub al-mu-tabarah, and takes the form of a learning community, which subsequently forms the dialectic of pesantren tradition in developing the santri-s mindset. The purpose of this research is to find out what traditions influence the santri-s mindset in shaping entrepreneurship, is there a significant influence between the dialectic of the pesantren tradition on the formation of the santri-s mindset, and which factors most influence the formation of the santri-s entrepreneurial mindset. The number of samples in this study were 160 santris from 4 (four) pesantrens in the province of Central Java determined by purposive sampling. Data collection techniques using questionnaires, interviews and observations. The data analysis method used is descriptive analysis and Structural Equation Modeling (SEM) analysis assisted by the LISREL 8.3 program. The results of the research describe that the dialectic variable of the pesantren tradition (kyai figure) has a large contribution, then the second variable that contributes to improving the mindset of the santri is the tradition of the learning community, while the tradition of studying al-kutub al-mu-tabarah gives the smallest influence on patterns thought the santri. Thus, the latent variable of dialectical tradition of the kyai figure and the learning community positively influences the santri-s entrepreneurial mindset by referring to the rules of Al-muhâfadhatu ‘alâ qadîmis shâlih wal akhdzu bil jadîdil ashlâh. This is different from the tradition of the study of al-kutub al-mu-tabarah which only has a small effect on the mindset of santris.