Unintentional posterior venous wall penetration during internal jugular vein (IJV) cannulation may cause critical arterial injuries in spite of ultrasound guidance. We aimed to evaluate whether small venous diameter and anterior venous wall tenting by a needle would be associated with posterior venous wall penetration, and to seek factors related to the venous wall tenting. We conducted a retrospective review in patients who underwent IJV cannulation. Using an ultrasound view obtained when puncturing, venous diameter, venous wall thickness, anterior venous wall tenting length, and needle angle were measured, and posterior venous wall penetration was determined. Eleven cannulations in 56 patients were assigned to posterior venous wall penetration. Small venous diameter (p = 0.004), and long anterior venous wall tenting (p = 0.007) were associated with posterior venous wall penetration. The longer anterior venous tenting would be expected with reducing needle angle (p = 0.004) or increasing anterior venous wall thickness (p = 0.006). In conclusion, small IJV and anterior venous wall tenting lead to posterior venous wall penetration. Anterior venous wall tenting is longer with reducing needle angle, or increasing the anterior venous wall thickness.