The purpose of this qualitative research study is to understand the process used for teacher-created online math assessments and the effect that online math assessments have on student engagement. Data for this qualitative study was collected and analyzed using Braun and Clarke’s (2006) thematic analysis which uses key conceptual foundations in a six-phase process. The study participants were middle school math teachers that taught a minimum of one course that required high-stakes end of year testing. Survey participants were recruited through an online survey. Data collection consisted of single interviews that were analyzed and compared. Data indicated that teachers prioritize the needs of diverse learners when creating online math assessments and when integrating technology to reinforce mathematical strategies. The data also indicated that teachers perceive the design features embedded in online math assessments to significantly influence student engagement. Finally, data indicated that technical issues and limitations pose significant challenges to the effectiveness and engagement of online math assessments.