Placental vascular anastomoses are traditionally thought to exist exclusively in monochorionic pregnancies. However, they have been reported in dichorionic twin pregnancies as well. In turn, twin to twin transfusion syndrome (TTTS) and twin anemia polycythemia sequence (TAPS) have also been noted to impact some of these gestations. Through discussion of one such case at our institution along with a review of the available literature, we review the proposed pathophysiology of placental vascular anastamoses in dichorionic twin gestations, and aim to raise awareness of the possibility of associated pathologies in dichorionic gestations. This is an emerging area of literature that will require future study to guide prenatal surveillance and mitigate morbidity.