German life insurance policies provide minimum interest rate guarantees. Usually, this guarantee is given in every single year. This type of contract poses a high risk on the insurer and restricts also the flexibility of the investment strategies. Therefore, new types of guarantees were developed, assuring for instance a certain minimum interest rate only at maturity of a contract. This considerably reduces the shortfall probability for insurance companies. In this paper, the interaction of different type of guarantees and the corresponding shortfall probabilities is investigated. We also study different types of investment strategies. In the investigation of shortfall probabilities, we develop a cutting-edge dynamic trading strategy with three variants: Type I, Type II, and Type III. Especially the matured trading strategy Type III yields low shortfall probabilities, and at the same time an exemplary distribution of maturity capital. Compared with the results of the well known CPPI strategy the new strategy of Type III shows a remarkable good performance. Contrary to the existing literature, jump diffusion processes are also used for the asset price models. Compared to classical models with geometric Brownian motion, this gives a considerable increase of shortfall probabilities. The results again demonstrate that in the literature dealing with this subject, the model risk is usually underestimated.