Background: Nowadays, complicated and painful surgical procedures are encouraged to be carried out in an ambulatory setting. Objectives: The current study aimed to assess 4-week postoperative pain profiles of 4 painful ambulatory surgical procedures. We analyzed the prevalence of and reasons for non-adherence and partial adherence of patients to a predefined treatment schedule after the ambulant surgery. Methods: The current study analyzed data from a large randomized trial by evaluating the effect of postoperative pain medication on acute postoperative pain at home during the first 4 postoperative days (POD) in patients scheduled for ambulatory hemorrhoid surgery, shoulder or knee arthroscopy, and inguinal hernia repair. Postoperative pain intensity was assessed at POD 0, 1, 2, 3, 4, 7, 14, and 28 via the Numeric Rating Scale (NRS). Adherence was assessed on POD 1, 2, 3, and 4. Results: Median average pain scores were above an NRS of 3 during the first postoperative week after shoulder arthroscopy and even above 4 during the first postoperative week after hemorrhoid surgery. 26% of patients undergoing shoulder arthroscopy and hemorrhoid surgery still had moderate pain 1 week after surgery. Median average pain scores were below an NRS of 3 during the whole study period after inguinal hernia repair and knee arthroscopy. 24.61% of patients did not use the study medication as prescribed, 5.76% of whom were non-adherent, and 18.85% were partially adherent. Conclusions: Each type of ambulant surgery has its unique postoperative pain profile. New strategies should be developed for pain therapy at home, particularly after the ambulatory arthroscopic shoulder surgery and hemorrhoid surgery. Non-adherence is uncommon if they are provided with a multimodal analgesic home kit together with clear verbal, written instructions, and intensive follow-up.