The present study endeavors to comprehensively examine the obstacles faced by elementary school students when attempting to grasp fundamental mathematical concepts pertaining to circles. Specifically focusing on Grade 4 students at SDN Cipondoh 2, Tangerang City. The primary objective is to shed light on the difficulties encountered by students in three core areas: calculating circle area and circumference, understanding the complex concept of π (pi), and accurately sketching circles utilizing a compass. Various tools are employed to scrutinize the obstacles students encounter, including tasks such as calculating circle area and circumference, comprehending the intricate π (pi) concept, and accurately sketching circles using a compass. The findings indicate that students encounter hurdles in computing circle area and circumference due to the need to understand underlying formulas and calculation procedures. Additionally, comprehending the π (pi) concept presents a notable challenge in circle calculations. Moreover, students struggle with precise and symmetrical circle drawing using a compass. The research outcomes provide valuable insights for formulating effective pedagogical strategies to help students overcome challenges in comprehending and applying circle geometry principles.