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What Is “Roll Risk” in the Context of Futures or Options Contracts?

Roll risk is the uncertainty associated with closing out an expiring derivative position and opening a new one in a further-out contract. Specifically, it is the risk that the price difference between the two contracts (the "roll yield") will be unfavorable at the time of the roll, leading to unexpected costs or a less effective hedge.

What Is the Risk of “Contango” When Rolling a Position?
What Is the Difference between Inflationary Yield and Real Yield in Staking?
What Is the “Roll Yield” and How Is It Calculated?
What Is the Impact of a High Pool-Switching Rate on the Effectiveness of the PPLNS System?