Over the last 2+ years, the Hauppauge School District has embarked on a journey to effectively integrate a variety of technologies into our classrooms to engage our students. To support teachers with timely and effective professional development in alignment with this vision, Hauppauge district leaders partnered with the Hauppauge Teachers Union and TEQ to facilitate online, asynchronous learning courses. This session will serve as a reflection of the journey, including the technical, contractual, logistical and practical considerations and challenges.