Bochdalek hernias are the most common congenital diaphragmatic hernias, followed by Morgagni hernias. The failure of closure of the pleuroperitoneal membrane results in a posterolateral foramen, which can remain silent until adulthood. They remain a rare pathology with nearly a hundred cases published. Its clinical presentation is variable, making its diagnosis challenging for clinicians. Additionally, its symptoms are not necessarily representative of the content of the hernia. Its management is balanced between the abdominal and the thoracic approaches. However, no guidelines or algorithms are available to help surgeons in the decision-making process. We report here four consecutive cases of symptomatic Bochdalek hernias. Each case has a singular presentation, and we share how they were approached at our institution. In particular, this series shows no reoccurrence in 10+ years of follow-up in two cases and 20+ in one case, underlying the importance of surgical management when Bochdalek hernias are symptomatic.