There are rumors that the Kardashian matriarch is joining forces with the music mogul for a project for Revolt TV and she definitely deepened everyone's curiosity by wearing a "Revolt" hat in one of the photos.
"Bad Boy 2014...Drive-by just to make sure he's takin care of business. #workaholics," she captioned the collage.
Most recently, Kris joined up with Diddy as part of the "Ciroc the New Year" campaign, which aims to encourage responsible driving during the holiday festivities.
We also know they've worked together in the past, with Diddy appearing on Kris' talk show last year, where he even got a little flirty with the 58-year-old!
We can't wait to see what these two could possibly be cooking up!
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Gallery | Kris Jenner's Biggest Photobombs