In an age when students are increasingly expected to demonstrate technology-based writing proficiency, fluency challenges with word processing programs can pose a barrier to successful writing when students are asked to compose using these tools. The current study was designed to determine whether differences existed in typing fluency and digital writing program (i.e., Microsoft Word) proficiency among students with and without learning disabilities (LD). Students' self-perceptions about their ability to use word processing tools were also explored to gain a basic understanding of how students perceived themselves as typists and writers. Results revealed students with LD were significantly less fluent at typing than their peers without LD, indicating that students with LD may need individualized assistance not only with essay composition but also with the technology tools they use to produce essays. Implications of results across measures and recommendations for future research and practice are discussed.