In the "Extended Vision" or "Wide Vision" caboose, the sides of the cupola project beyond the side of the carbody. Rock Island created some of these by rebuilding some standard cupola cabooses with windowed extensions applied to the sides of the cupola itself, but by far the greatest number have the entire cupola compartment enlarged. This model was introduced by the International Car Company and saw service on most U.S. railroads. The expanded cupola allowed the crew to see past the top of the taller cars that began to appear after World War II  and also increased the roominess of the cupola area.

Additionally, Monon Railroad had a unique change to the extended vision cabooses. They added a miniature bay to the sides of the cupola to enhance the views further. This created a unique look for their small fleet. Seven of the eight Monon-built cabooses have been saved. One was scrapped after an accident in Kentucky. The surviving cars are at the Indiana Transportation Museum (operational), the French Lick Museum (operational), the Kentucky Railroad Museum (fire damaged), and the Bluegrass Railroad Museum (unrestored but servicable). The remaining three are in private collections.