Background Medical students commonly experience Medical Student Syndrome (MSS), a condition where they compare their vague symptoms to the medical problems and life-threatening diseases they are learning about in medical school, even though their health profile is clean. Our research aims to investigate the symptoms of MSS (anxiety-related illness) and hypochondriasis, as well as their impact on the lives of students. Additionally, we aim to study various types of personalities and, finally, investigate the demographic determinants of MSS and their interactions with various personality types among medical students in Egypt in the period between September and December 2023. Methods This analytical cross-sectional study targeted 300 students recruited from the medical field at Zagazig University. The data was collected using a self-administered questionnaire, which consisted of four main components: demographic data, the MSS questionnaire, the personality-type questionnaire, and the MSS’s impact. The collected data was coded and analyzed using R statistical software. Results Out of the 300 medical field students recruited, 261 (87.0%) were Egyptian, 164 (54.67%) were female, and 216 (72.0%) were medical students without co-morbidity. 181 (60.33%) were aware of the MSS. Only 11 (3.67%) students met all criteria of the DSM-V for anxiety disorder, while 20 (6.67%) students met all criteria of the DSM-IV for hypochondriasis. The most common anxiety symptoms were difficulty sleeping (50.00%), lack of productivity or difficulty concentrating (44.0%), and rapid heart rate (31.67%). In terms of personality, being sympathetic and warm received the highest median of 6.00 while being critical and quarrelsome received the lowest median score of 2.00. The health anxiety score significantly negatively correlates with dependable and self-disciplined personality traits, while it significantly positively correlates with anxious and upset personality traits. Conclusion Around one-third of the sample experienced preoccupation with fears of having a serious disease, with a trivial number of students meeting the criteria for an anxiety disorder or hypochondriasis. More than one-third reported negative impacts on sleep, productivity, concentration, and heart rate. Females, Egyptian students, those from rural areas, and dentistry students had higher anxiety scores, whereas medical students had the lowest scores.