Sufi orders of Islam are mystical brotherhoods aiming to raise “mature selves” since their establishment in the 12th century. An indispensable element of Sufi orders is the relationship between the sheikh/master and the dervish/disciple. For Sufis, true spiritual progress is impossible without being attached to a spiritual guide. This paper will examine how the sheikh-dervish relationship is experienced in today’s Turkey. Using the data from in-depth interviews I conducted with thirty members of three Sufi groups (İskenderpaşa branch of Nakşibendis, Erenköy branch of Nakşibendis and Mevlevis), I will seek answers to the following questions: (1) How and by what means do they establish relations with their sheikhs? (2) What new and old technologies are used to maintain their relationship? (3) How do they legitimize and relate the elements in their sheikh-dervish relationships to tradition? (4) What kind of an ideal sheikh-disciple relationship do they envision? Based on a comparative and historical approach, descriptive analysis, and partial use of discourse analysis method, the research results show some basic strategies of sheikh-disciple relationships: (1) emphasizing face-to-face relationships, (2) preference for communication with the elders through texts, (3) highlighting the state of bond/spiritual union, (4) utilizing many communication tools such as radio, streaming, television, and books, and (5) family relations. This paper will emphasize the significance of modernity and the political processes that diversify the sheikh-dervish relationship, thereby offering an empirical contribution to contemporary Sufism studies.