This chapter is devoted to the dynamic risk management of the investment portfolio using future contracts. The number of futures for each portfolio asset, which is determined by portfolio effectiveness and acceptability of risk at each step, serves as a control parameter. The authors define effective portfolios as the ones of the minimum variance with the expected return greater than or equal to the specified value. Risk is measured by the probability of losing a certain part of the portfolio value. Effective adaptive strategies of portfolio risk management are proposed and their comparative analysis is carried out on a concrete example. In order to determine risk management strategies, the authors implement simple methods of volatility forecasting and correlation of relative changes of price data based on exponential moving average. © 2018, IGI Global. All rights reserved.