Boots for Kilimanjaro

I want to start breaking in a pair of new boots for a hike up Mt. Kilimanjaro in six months. We'll have porters, so we'll just be carrying light day packs. Do I need stiff-soled backpacking boots or can I use more comfortable flexible soled hiking boots?

Since you will have the government-mandated porters and only be carrying daypacks with lunch, water, and jackets, you can do just fine with light boots. Also, your hiking days will be fairly short, which fits with the light boots. You might get rain (even in the "dry" season), so you might not want to use just trail-running shoes. Whether you want high top or mid depends on how strong your ankles are. The trails are pretty rocky in places.

Are you going by the "Coca Cola" or "Whiskey" route? You probably want to know that the Western Breach route had major rockfall this January, which killed a couple clients and a number of porters. With the meltoff, this might not be the best choice for a few years.