Background/Objectives: In recent years, there has been a noticeable increase in the rates of caesarean section (CS), being one of the most commonly performed surgical procedures. For the following pregnancy, the previous CS represents the backbone of the risks and complications, such as uterine scar formation, uterine rupture, massive bleeding, and serious negative outcomes for both the mother and child. Our study followed patients with a history of CS from the birth planning prenatal check-up to delivery. Methods: We reviewed the records of 125 pregnant women with previous CS who presented in the third trimester for a prenatal check-up and completed our questionnaire from March 2021 to April 2022 in the Clinic of Obstetrics and Gynecology, Diakoneo Diak Klinikum Schwäbisch Hall, Germany. Results: Before the prenatal check-up, 74 patients (59.2%) preferred vaginal delivery (VD), while 51 (40.8%) preferred CS. After discussing birth planning with the obstetrician, 72 women (57.6%) decided upon VD, while 53 (42.4%) preferred CS. Ultimately, 78 (62.4%) of women gave birth through CS (either planned or by medical necessity) and 47 (37.6%) gave birth vaginally (either natural or per vacuum extraction). Conclusions: VD for patients with CS in their medical history is a real option. The patient must be well informed about the risks and benefits of the medical situation and should be empowered and supported on their chosen mode of delivery, which should be respected.