Background: In Germany, there are two different active substances, levonorgestrel (LNG) and ulipristal acetate (UPA), available as emergency contraception (the “morning after pill”) with UPA still effective even 72 to 120 h after unprotected sexual intercourse, unlike LNG. Emergency contraceptive pills have been available without a medical prescription since March 2015 but are still only dispensed by community pharmacies. The aim of this study was to determine the counselling and dispensing behaviour of pharmacy staff and the factors that may influence this behaviour in a scenario that intends that only the emergency contraceptive pill containing the active substance UPA is dispensed (appropriate outcome). Methods: A cross-sectional study was carried out in the form of a covert simulated patient study in a random sample of community pharmacies stratified by location in the German state of Mecklenburg-Vorpommern and reported in accordance with the STROBE statement. Each pharmacy was visited once at random by one of four trained test buyers. They simulated a product-based request for an emergency contraceptive pill, stating contraceptive failure 3.5 days prior as the reason. The test scenario and the evaluation forms are based on the recommended actions, including the checklist from the Federal Chamber of Pharmacies. Results: All 199 planned pharmacy visits were carried out. The appropriate outcome (dispensing of UPA) was achieved in 78.9% of the test purchases (157/199). A significant correlation was identified between the use of the counselling room and the use of a checklist (p < 0.001). The use of a checklist led to a significantly higher questioning score (p < 0.001). In a multivariate binary logistic regression analysis, a higher questioning score (adjusted odds ratio [AOR] = 1.41; 95% CI = 1.22–1.63; p < 0.001) and a time between 12:01 and 4:00 p.m. (AOR = 2.54; 95% CI = 1.13–5.73; p = 0.024) compared to 8:00 to 12:00 a.m. were significantly associated with achieving the appropriate outcome. Conclusions: In a little over one-fifth of all test purchases, the required dispensing of UPA did not occur. The use of a counselling room and a checklist, the use of a checklist and the questioning score as well as the questioning score and achieving the appropriate outcome are all significantly correlated. A target regulation for the use of a counselling room, an explicit guideline recommendation about the use of a checklist, an obligation for keeping UPA in stock and appropriate mandatory continuing education programmes should be considered.