Background: Similar to most imaging procedures, the high quality of images is a key factor in ensuring that mammography delivers its full potential benefits. Radiographers play a central role in the acquisition of high-quality images, as they are responsible for not only breast positioning and compression, but also quality control and patient care. Objectives: To identify the challenges and difficulties of radiographers in daily practice and to determine the main components of mammography that require further training and education. Patients and Methods: An online survey was conducted to collect data regarding the radiographers’ demographic data, institution profile, image assessment tools, mammography challenges, quality control, and continuing professional development. Results: A total of 73 radiographers participated in this study, the majority of whom were full-time radiographers with a bachelor’s degree in radiography. Less than half of the participants had been a mammographer for more than five years. The American College of Radiology (ACR) criteria were the most familiar image quality assessment tool (52%). The most frequently used scale to evaluate image quality was posterior breast tissue visualization on both craniocaudal (CC) and mediolateral oblique (MLO) views, followed by the pectoral muscle volume determined on the MLO view. Overall, positioning, artifacts, and compression were the main reasons for repeat mammography. Also, wheelchair-bound patients, overweight patients, and breast compression were the greatest challenges of patient positioning. Conclusion: This pilot study highlighted the importance of developing in-house training courses for radiographers, which focus on patient positioning, image quality assessment, and patient-centered needs to improve practice standards. However, further studies on a larger sample size are needed to validate the present results.