Background: This study aimed to examine the association among past traumatic events, high-risk pregnancy, delivery complications, and postpartum posttraumatic stress (PTS) symptoms. Methods: The final convenience sample consisted of 1071 Jewish women at midpregnancy. Data were gathered at three time points (during pregnancy and 1 month and 6 months after childbirth) through self-report questionnaires. Results: There was a higher percentage of high-risk pregnancy among those who reported a history of traumatic events. Although the total score of PTS symptoms did not correspond with high-risk pregnancy, the intrusion and avoidance subscales did. Furthermore, a history of traumatic events as well as prenatal PTS symptoms, prenatal depression, and the subjective pain and distress during delivery accounted for postpartum PTS symptoms. Prenatal depression was found to account for delivery complications. Conclusions: Findings indicate that a history of trauma should be considered a risk factor for high-risk pregnancy and for postpartum PTS symptoms.