The object-oriented programming paradigm has gained popularity in industry and academia, and Java is becoming the language of choice. Yet, it can be a difficult language to learn, with many hurdles for novice programmers. This chapter describes our experiences transitioning to Java as the first programming language in an information technology Masters program. Careful consideration was given to a variety of factors, including when to introduce object-oriented concepts, which integrated development environment to use, and how to support students with minimal prior experience. The impact of these choices on the learning experience is described, and the factors that led to the successful implementation of Java as a first programming language are presented.