Our medical and dental insurance plan year is always July 1st - June 30th. School year employees pay their portion of the insurance benefit from September - June when they return to school. The District fronts the cost of insurance for the months of July and August and the employee re-pays over the course of the year. If you have a life-changing / qualifying event and need to make a change mid-year, or drop coverage, the insurance contributions will be reconciled for actual months of coverage.