Fetal malpositions and cephalic malpresentations are well-recognized causes of failure to progress in labor. They frequently require operative delivery, and are associated with an increased probability of fetal and maternal complications. Traditional obstetrics emphasizes the role of digital examinations, but recent studies demonstrated that this approach is inaccurate and intrapartum ultrasound is far more precise. The objective of this review is to summarize the current body of literature and provide recommendations to identify malpositions and cephalic malpresentations with ultrasound. We propose a systematic approach consisting of a combination of transabdominal and transperineal scans and describe the findings that allow an accurate diagnosis of normal and abnormal position, flexion, and synclitism of the fetal head. The management of malpositions and cephalic malpresentation is currently a matter of debate, and individualized depending on the general clinical picture and expertise of the provider. Intrapartum sonography allows a precise diagnosis and therefore offers the best opportunity to design prospective studies with the aim of establishing evidence-based treatment. The article is accompanied by a video that demonstrates the sonographic technique and findings.