This study presents a unique assessment of executive functioning (EF) among postsecondary students with disabilities, with the aim of understanding the extent to which students with different disabilities and in different age groups assess their own difficulties with relevant and educationally-adaptive skills such as planning, initiating, managing time, staying on task, and controlling emotions. Students from a large Midwest public university applying for and/or receiving services at a university-based disability office (n = 50) completed the Behavior Rating Inventory of Executive Function-Adult Version (BRIEF-A) and a demographic questionnaire. Study groups were formed according to participants' self-reported disability or disabilities--including attention deficit hyperactivity disorder (ADHD), psychiatric disabilities, learning disabilities, traumatic brain injury, autism spectrum disorder, deaf and hard of hearing, and/or visual impairment--as well as those reporting single versus multiple disabilities and freshman versus all other class standings. Results revealed elevated EF ratings by students in the ADHD and psychiatric groups, particularly with regard to metacognitive skills. Freshman students reported less frequent EF challenges than older students, and identifying with more than one disability group was not a risk factor for elevated EF scores. Practical implications are discussed in terms of the utility of EF self-assessment in this population, and in supporting metacognitive strategies for postsecondary students with disabilities.