Background and objectives: Adequate pain management is a major challenge of public health. The majority of students graduating from medical schools has insufficient education and experience with patients suffering pain. Not enough is being taught regarding pain in non-verbal patients (children, critically ill in the intensive care unit, demented). Chronic pain is the most difficult to optimize and requires appropriate preparation at the level of medical school. Our aim was to evaluate attitudes, expectations and the actual knowledge of medical students at different levels of their career path regarding the assessment and treatment of acute and chronic pain. Materials and Methods: We performed an observational cross-sectional study that was based on a survey distributed among medical students of pre-clinical and post-clinical years at the Pomeranian Medical University in Szczecin, Poland. The survey included: demographic data, number of hours of formal pain teaching, actual knowledge of pain assessment, and pain treatment options in adults and children. Results: We received responses from 77/364 (21.15%) students and 79.2% of them rated the need to obtain knowledge regarding pain as very important (10/10 points). Post-clinical group declared having on average 11.51 h of acute pain teaching as compared to the 7.4 h reported by the pre-clinical group (p = 0.012). Graduating students also reported having significantly more classes regarding the treatment of chronic pain (6.08 h vs. 3.79 h, p = 0.007). The average level of comfort in the post-clinical group regarding treatment of acute pain was higher than in the pre-clinical group (6.05 vs. 4.26, p = 0.006), similarly with chronic pain treatment in adults (4.33 vs. 2.97, p = 0.021) and with pain treatment in children (3.14 vs. 1.97, p = 0.026). Conclusions: This study shows that education about pain management is a priority to medical students. Despite this, there continues to be a discrepancy between students’ expectations and the actual teaching and knowledge regarding effective pain management, including the vulnerable groups: chronic pain patients, children, and critically ill people.