The increased interest in Ottoman studies across various fields in the last decade resulted in a rise in the number of North American universities offering Ottoman Turkish language courses and development of online Ottoman Turkish dictionaries, word solvers, and various digital humanities projects. In this presentation I will focus on challenges in Ottoman Turkish classrooms posed by both of these developments. In the first part of the presentation I will describe how the willingness of the universities to offer Ottoman Turkish in their programs yet their lack of commitment in long term planning for instruction create problems for instructors and students alike, and what strategies and planning we come to rely on to help students advance their Ottoman Turkish. In the second part of the presentation I will discuss the teaching methods, print and digital sources that I have come to trust to equip students with better understanding of Ottoman grammar and orthography.