The Kargil operation was an audacious attempt to seize an opportunity of historic proportions. Indian troops predictably vacated posts along the Line of Control (LoC) as they retreated to winter positions – a normal measure taken by both Indian and Pakistani forces to reduce the strains on forces during the harsh winter months. Pakistani planners aimed to seize this unprotected territory to the maximum feasible limit, with an eye on interdicting National Highway 1A, the strategically important Indian road that runs between Srinagar and Leh. But the plan's boldness also made it dangerous and ultimately untenable. Its success would require hundreds of troops to infiltrate across the LoC and maintain their positions for weeks without being detected. After their inevitable discovery, they would have to hold off Indian counterattacks until the onset of winter, which would close the passes, halt military operations, and allow Pakistani infiltrators to harden their positions. This military fait accompli would enable Pakistan to redraw the LoC.

The operation's planners seemed convinced that India would not expand the conflict elsewhere along the LoC or the international border, and that the international community would view the Kargil incursion as part of the normal pattern of military activity along the LoC, similar to India's occupation of the contested Siachen Glacier fifteen years before. While some of the calculations of Pakistani planners were borne out by events, the faulty assumptions they made, when combined with tactical missteps on the ground, doomed the Kargil operation to failure.