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Simple Summary: Here, we investigated how Octopus vulgaris approached and solved a problem required for obtaining food from a puzzle box. We also explored the relationship between individual octopuses' problem-solving abilities and various behavioural characteristics (e.g., their interest in novel objects), and biotic and environmental factors (age, season, and site of capture). We found that octopuses more inclined to approach new objects were quicker to approach the puzzle box and more likely to succeed in opening it, but they did not reach the solution before other individuals. This suggests that an excessive inclination towards novelty could hinder problem-solving efficiency. The study also revealed that the season and the fishing site are important drivers of octopuses' behavioural differentiation. Our findings offer valuable insights into the individuality of octopuses. By presenting individual Octopus vulgaris with an extractive foraging problem with a puzzle box, we examined the possible correlation between behavioural performances (e.g., ease of adaptation to captive conditions, prevalence of neophobic and neophilic behaviours, and propensity to learn individually or by observing conspecifics), biotic (body and brain size, age, sex) and abiotic (seasonality and place of origin) factors. We found more neophilic animals showing shorter latencies to approach the puzzle box and higher probability of solving the task; also, shorter times to solve the task were correlated with better performance on the individual learning task. However, the most neophilic octopuses that approached the puzzle box more quickly did not reach the solution earlier than other individuals, suggesting that strong neophilic tendency may lead to suboptimal performance at some stages of the problem-solving process. In addition, seasonal and environmental characteristics of location of origin appear to influence the rate of expression of individual traits central to problem solving. Overall, our analysis provides new insights into the traits associated with problem solving in invertebrates and highlights the presence of adaptive mechanisms that promote population-level changes in octopuses' behavioural traits. [ABSTRACT FROM AUTHOR]