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A calendar year deductible resets. Detailed comparison pros and cons. Web learn the difference between calendar year and plan year deductibles in health insurance policies. Web plan year vs calendar year: Web essentially, a plan year revolves around the start and end dates that an employer designates for their. Web a calendar year deductible, what most health plans operate on, begins on january 1st and ends on december 31st. The choice between a plan year and a calendar. All individual plans now have the calendar year match the.