The development of pesantren from time to time illustrates its significant role within communities. Its dynamic development appears clearly as a result of its ability to adapt into the external condition. Its communities are well-known with their social skills in dealing with external culture that comes from all types of challenges coming from outside. Pesantren has an internal mechanism to adapt into a new trend, due to the development of its function and differentiation. The empirical experiences show the ability of four imperative functions of pesantren, namely: high ability to adapt into the external world, wide-ranging goal achievement, integrative ability of unifying the unique aspects of pesantren as sub-culture, and ability in preserving the pesantren’s tradition with the principle “maintaining the old good tradition and gaining a new better tradition”. Differentiation mechanism is a gradual transformation process of pesantren that causes the steady increase of new units within it to perform their functions more effectively. This response leads to various models of pesantren.