This article draws on the fact that pesantren have been widely built in the country, as the oldest educational base ever in Indonesia. So various dynamics have been experienced according to current developments. Nevertheless, it is a social force that grows and develops within society. Pesantren has its character and concentration on scientific development and has a significant self-defense mechanism (struggle to survive) in building independence. So it is not excessive that various efforts have been made to build independence, including; developing agricultural businesses, agriculture, plantations, cooperatives, television, radio printing, and various other productive businesses. The objectives of this study are to (1) describe the various productive business activities of students that pesantren has developed, (2) to describe artificial intelligence used by students as a new force in developing pesantren businesses, (3) connect artificial intelligence with pesantren efforts in developing institutional independence. This research was located in Ponorogo, East Java. The selection of Gontor as a research location is because Gontor has a tradition of developing institutional independence that has been tested for more than 90 years. Furthermore, as many as 267 students as a population, and a sample of 159 students as a sample in this study. The technique of measuring the sample magnitude using the Slovin formula (n=N/1+N.e2). Data collection techniques are carried out by random sampling. Data analysis techniques with product moment (Pearson correlation). The results of the research findings: (1) Various conventional businesses (agriculture, plantations, fisheries, and so on) have been developed to build the institution’s independence in Gontor. (2) Technology-based businesses have also been developed to support the development of business units run by "digital-based MSMEs". (3) There is a positive and significant relationship between students’ perceptions of artificial intelligence development and institutions' independence in Islamic boarding schools, especially Gontor. Thus, this research proves that technological advances need to be addressed wisely by pesantren and not make them enemies but a medium for developing the independence of pesantren institutions, without having to remove the identity of the pesantren itself.