During the last decade, field experiments regarding the study of common pool resource governance have been performed that replicated earlier findings of laboratory experiments. One of the questions is how the decisions made by participants in rural communities are influenced by their experience. This paper presents the results of field experiments in Colombia and Thailand on fishery resources. Context information is derived from the communities via in-depth interviews, surveys and role playing exercises. The use of different methodological tools allowed to link decisions in field experiments with contextual variables for two fishery villages. Explanation of core variables in social dilemmas is given, the degree of cooperation levels, preferred rules, rule compliance and enforcement. Main findings include: i) fishermen made decisions in the field experiments that reflected their own experience and context, ii) agreements for rule crafting are possible only under specific conditions that guarantees livelihoods and sustainability, iii) the broader context determines cooperation levels at a local level, iv) inequalities in the sanctioning of rule breakers decrease the possibilities of reaching cooperation agreements, and v) high levels of trust among local fishermen is not a sufficient condition for resource sustainability, when trust in external rule makers and enforcers is low.