Systems and methods in accordance with embodiments of the invention operate an insurance enabled hybrid game, including: a gambling game providing a game of chance and an entertainment game providing a game of skill, where the insurance enabled hybrid game utilizes a multisession module constructed to: activate an insurance proposition associated with an insurance trigger event in accordance with an insurance activation rule to generate at least one insurance relationship between an insurance safeguard that can be applied in exchange for an insurance fee, and where a challenge is a gameplay event dependent upon player action with a negative outcome of the challenge defined by the insurance safeguard; collect an insurance fee; and apply an insurance safeguard associated with the collected insurance fee by altering insurance enabled hybrid game gameplay in response a negative outcome of a challenge detected by the insurance module that mitigates the negative outcome.