Close! Throughout a calendar year, the fees you acquire for health services are added towards reaching your deductible total. Once the deductible is reached, the health insurance company will pay for the services needed. For example, you start with a deductible of $2,000 each year. After a few visits to the doctor and medical tests, you have paid $500 towards your deductible of $2,000 in August. In September, you end up needing knee surgery, which costs $10,000. Rather than paying the full amount, you are responsible for paying your remaining deductible of $1,500, then the insurer covers the rest or a portion (if you have coinsurance) until next year when it starts all over again.