This research study investigated the perspectives of urban K-12 educators regarding the challenges they confronted when endeavoring to implement online learning effectively. The quantitative investigation involved 204 full-time urban teachers in a Midwestern state, all completing a researcher-developed questionnaire. The findings illustrated that participants encountered diverse obstacles, encompassing aspects related to readiness, along with external and internal factors. Educators identified a need for more time for crafting impactful online lessons as the most prominent barrier to preparedness. Respondents selected dependable student access to the internet at home as the primary external factor influencing their capacity to instruct in a virtual setting. The findings offer a specific perspective and an opportunity to stimulate dialogues concerning the provision of resources to enhance preparedness. By cultivating a deeper comprehension of how urban educators perceive their aptitude for online teaching, this study empowers current educators, educational leaders, and teacher preparation faculty to formulate more contemplative curricula. Future research should expand across multiple states to better equip aspiring educators and keep practicing professionals informed about empirically supported best practices.