A target is protected by the defender and attacked by an attacker launching sequential attacks. For each attack, a contest intensity measures whether the agents’ efforts have low or high impact on the target vulnerability (low vs. high contest intensity). Both the defender and the attacker have limited resources. It is assumed that the attacker can observe the outcome of each attack and stop the sequence of attacks when the target is destroyed. Two attacker objectives are considered, that is, to maximize the target vulnerability or to minimize the expected attacker resource expenditure. The article addresses the following three questions: whether the attacker should allocate its entire resource into one large attack or distribute it among several attacks; whether geometrically increasing or decreasing resource distribution into a fixed number of sequential attacks is more beneficial than equal resource distribution; and how the optimal attack strategy depends on the contest intensity.