Greater awareness of possible iatrogenic esophageal perforation (EP) is needed. Though rare, EP is a legitimate health risk as it may lead to long-term morbidities. This study presents and discusses iatrogenic EP in a subset of preterm infants. Using radiographic images, we study and describe the consequences of the orogastric/nasogastric tube position (in radiographic images). We analyze the possible influence of histological chorioamnionitis on the development of esophageal perforation. This retrospective study examines the hospital records of 1149 preterm infants, 2009–2016, with very low birth weight (VLBW) and iatrogenic EP, comparing mortalities and morbidities between the two groups of preterm infants who had birth weights (BWs) of less than 750 g and were less than 27 weeks gestation age at birth: one group with iatrogenic esophageal perforation (EP group) and one group without perforation (non-EP group—the control group). Histopathological chorioamnionitis of the placenta showed no statistically significant differences between the groups. The only statistically significant difference was in the air leaks (p = 0.01). Three types of nasogastric tube (NGT) X-ray location were identified, depending on the place of the perforation: (1) high position below the carina mimicking esophageal atresia; (2) low, intra-abdominal; (3) NGT right pleura-directed. We also highlight the particular symptoms that may be indicative of EP due to a displacement of the nasogastric tube.