Finite element buckling analysis of insulated transition flue ducts is carried out to determine the critical buckling load multipliers when subjected to axial compression for design process. Through this investigation, the results of numerical computations to examine the buckling strength for different possible duct shapes (cylinder, and circular-to-square) are presented. The load multipliers are determined through detailed buckling analysis taking into account the effects of geometrical construction and duct plate thickness which have great influence on the buckling load. Enhancement in the buckling capacity of such ducts by the addition of horizontal and vertical stiffeners is also investigated. Several models with varying dimensions and plate thicknesses are examined to obtain the linear buckling capacities against duct dimensions. The percentage improvement in the buckling capacity due to the addition of vertical stiffeners and horizontal Stiffeners is shown to be as high as three times for some cases. The study suggests that the best location of the horizontal stiffener is at 0.25 of duct depth from the bottom to achieve the maximum buckling capacity. A design equation estimating the buckling strength of geometrically perfect cylindrical-to-square shell is developed by using regression analysis accurately with approximately 4% errors.