The present concepts may automate and optimize deployment to a cloud computing fleet. Artificial intelligence and/or optimization algorithms may be used to find optimal deployment parameters (e.g., deployment order of computers in the fleet) that minimize deployment time and minimize deployment risk. For example, machine-learning prediction models may be used to generate a shortest path graph problem models a deployment planning problem. Then, optimization algorithms may be used to efficiently find approximations of Pareto-optimal solutions to the shortest path graph problem. Depending on the preferred level of time and risk, one of the solutions may be used to run the deployment.