Animals often engage in contests over limited resources. The probability of winning a contest is primarily determined by the individual's fighting ability relative to its opponent and the perceived value of the disputed resource. Individuals of the hermit crab Calcinus californiensis frequently fight over gastropod shells. We conducted a free-choice experiment to assess the factors that determine individuals’ choice of opponent, contest initiation, and contest resolution. We placed hermit crabs occupying two shell species into a large container and monitored agonistic interactions between crabs. We assessed the asymmetries in fighting ability based on the differences in body mass between the opponents. The shell species and fit (i.e., shell size relative to crab body size) were used as measures of the objective and subjective resource value, respectively. Motivation influenced contest initiation; the crabs occupying too-tight shells were more likely to initiate a contest than the ones in looser-fitting shells. In most cases, the attackers fought for a shell with a looser fit, even if that meant losing a tighter-fitting shell of the preferred shell species. The fighting success for attackers was positively associated with the number of bouts of rapping and the shell size improvement. However, success was negatively correlated with body size asymmetry; attackers that chose opponents larger than themselves were more likely to evict their opponent than the attackers that chose opponents that were smaller. Experimental designs that allow animals to select their own opponents, rather than assigning specific opponents, can strongly contribute to knowledge of agonistic interactions.Significance statementFighting dynamics are commonly assessed by estimating the influence of the resource-holding potential and resource value in pair-matched opponents. Here, however, we examined the influence of asymmetries in resource-holding potential and the objective and subjective value of gastropod shells on the choice of a contender and contest resolution through a free-choice opponent experiment in hermit crabs. The contest initiation was driven by the motivation to obtain a better gastropod shell species or one with a better size fit—factors which are known to improve individual fitness. Furthermore, fighting success was associated with an individual's persistence in displaying aggressive behaviors and its motivation to obtain a better resource. However, contrary to the predictions of game theoretical models, fighting success was higher when attackers chose opponents larger than themselves. Our results highlight the relevance of assessing fighting under more natural conditions by allowing animals to select their opponents.