October: gather information
Request plan documents from HR or create a marketplace account. Export a list of prescriptions from your pharmacy app. Write down every provider your household saw in the last 12 months.
Note any planned care: physical therapy, pregnancy, surgery, or new diagnoses. These shift which plan is cheapest.
November: compare total cost
Build a simple spreadsheet: plan name, premium, deductible, OOP max, and expected visits. Marketplace shoppers should update income estimates. Wrong income data can mean repaying tax credits later.
Schedule a benefits meeting at work if offered. Ask whether your employer is changing carriers or contribution levels.
December: enroll and confirm
Submit elections before the deadline. Screenshot confirmation pages. For marketplace plans, pay the first premium by the insurer's deadline or coverage may not start.
If you use auto-pay, verify the bank account on file. A rejected payment is a common reason for accidental loss of coverage in January.
January: verify active coverage
Log into your insurer portal and confirm ID cards are available. Call your PCP office to update insurance on file. Set a reminder to review the first EOBs for errors.