Context-dependence is fundamental to risky monetary decision-making. A growing body of evidence suggests that temporal context, or recent events, alters risk-taking at a minimum of three timescales: immediate (e.g. trial-by-trial), neighborhood (e.g. a group of consecutive trials), and global (e.g. task-level). To examine context effects, we created a novel monetary choice set with intentional temporal structure in which option values shifted between multiple levels of value magnitude (“contexts”) several times over the course of the task. This structure allowed us to examine whether effects of each timescale were simultaneously present in risky choice behavior and the potential mechanistic role of arousal, an established correlate of risk-taking, in context-dependency. We found that risk-taking was sensitive to immediate, neighborhood, and global timescales, increasing following small (vs. large) outcome amounts, large positive (but not negative) shifts in context, and when cumulative earnings exceeded expectations. We quantified arousal with skin conductance responses, which were specifically related to the global timescale, increasing with cumulative earnings, suggesting that physiological arousal captures a task-level assessment of performance. We complimented this correlational analysis with a secondary reanalysis of risky monetary choices following the double-blind administration of propranolol and a placebo during a temporally unstructured choice task. We replicated our behavioral finding that risk-taking is context-sensitive at three timescales but found no change in temporal context-effects following propranolol administration. Our results demonstrate that risky decision-making is consistently dynamic at multiple timescales and that arousal is likely the consequence, rather than the cause, of temporal context in risky monetary decision-making.