As the Allied juggernaut steamed across Europe and the Pacific bringing World War II to a close, Cessna was developing a new line of single engine airplanes to fill what management optimistically foresaw as a burgeoning post war market for "family cars of the air." The 120/140 line was already in work in 1944 as was initial planning for the 170. And yet, the pre war popularity of the Airmaster series (arguably one of the best looking high wing taildraggers), led management to authorize an updated version—the 190, retaining the basic Airmaster lines but with more interior room. The new aircraft was to capitalize on technological developments such as constant speed propellers, Wittman spring steel landing gear, control wheels to replace the sticks, and a semi monocoque metal fuselage (a design wherein the outer skin carries the majority of the stress).

As in the Airmasters, the 190's steel-tube front wing spar was full depth and, in the fuselage carry through section, protruded into the cabin's headroom such that the pilot and front seat passenger had to be wary of banging their heads and the rear seat passengers could not see around it. To correct the problem on the prototype, a new spar was made from aluminum bar stock and secured with bolts and stress plates overdesigned to 150% of required strength to preclude problems due to the brittleness of the bar stock.

First flight of the prototype 190, with fabric covering, was on 7 December 1944 with a 225 horsepower Jacobs engine borrowed from the AT 17 line. The second prototype, a five place all metal design, was upgraded to a 300 horsepower Jacobs engine and flew for the first time on 15 October 1945. Several problems cropped up during flight testing: directional overcontrol due to the large vertical tail and rudder (corrected with a dorsal fin); a tendency for the tailwheel to shimmy (corrected with a new tailwheel fork); a tendency to drop a wing at the stall (corrected by adding inboard stall strips); inadequate cabin heat (corrected with a gas-fired combustion heater under rear seat); and some oil cooling problems. The only problem with the gas fired heaters was that the intake and exhaust tubing coming through the aircraft's belly had to be individually trimmed and fitted by hand for every aircraft.

Development of both the 190 and 195 models continued in parallel, with the 190s eventually being delivered with only a 240 horsepower Continental W 670 23 radial engine and the 195s getting the 300-horsepower Jacobs radial engines. Options included the 245 horsepower R 755 9 (customer furnished only), the 275 horsepower R 755 B2, and the more popular 300 horsepower R 755 A2.

Although the Continental engine on the 190 was smoother, it lacked the power of the bigger Jacobs, which tended to run rough and leak oil. . .leading to nicknames like "shaky Jake" and "bleeding Jake." In the 3,350 pound 195, the extra climb rate convinced most pilots to buy the bigger 300 horsepower engine. Production of the 195 started in July of 1947, while production of the 190…