VOLUME 3 · CHAPTER 8 OF 8

A Yearly Health Insurance Review

A routine to run each fall: know your enrollment windows, review the year you had, read what is changing, verify the network, compare total cost, reset HSA and FSA amounts, and react to life events.

5 min readDeep dive0 worked examplesupdated 2026-10-01
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Health plans change every year even when you change nothing. Premiums rise, deductibles move, a hospital leaves the network, a drug moves to a higher tier, an employer cuts its HSA deposit. Most people renew automatically and find out at the pharmacy counter or in the emergency room. This chapter turns everything in this book into one routine you can run each fall in a couple of hours, plus the events that should make you run it again mid-year.

Know your windows

You can only change coverage at certain times, so the first step is knowing which window applies to you.

CoverageWhen you can change it
Employer planThe employer's open enrollment, usually a few weeks in the fall; dates vary
MarketplaceOpen enrollment on HealthCare.gov starts November 1; the end date depends on your state and the plan year
MedicareOctober 15 to December 7 for any change; January 1 to March 31 for one switch out of a Medicare Advantage plan

Outside these windows, only a qualifying event opens a special enrollment period, covered at the end of this chapter. Put next year's windows in your calendar now, with a reminder two weeks before each opens so the review is not squeezed into the final days.

Step 1: look back at the year you had

Start with facts, not guesses. From your insurer's member portal, download the year's claims or Explanations of Benefits. From your own records, collect premiums, pharmacy receipts and any HSA or FSA statements. Then total:

  • premiums paid
  • what you paid for care: deductible, copays and coinsurance
  • whether you reached the deductible or the out-of-pocket maximum, and in which month
  • how many visits of each kind, and every regular prescription
  • any money left in an FSA, or forfeited

This is the "expected year" from chapter 2. A year in which you never came close to the deductible points one way; a year in which you hit the out-of-pocket maximum by spring points the other.

Step 2: read what is changing

Your plan must tell you what changes next year. Employers publish a new Summary of Benefits and Coverage for each plan; Marketplace insurers send a renewal notice; Medicare plans send an Annual Notice of Change by the end of September. Read them for five things:

  1. Premium, your share after any employer contribution or tax credit.
  2. Deductible and out-of-pocket maximum.
  3. Network. Is every doctor, hospital, lab and pharmacy you use still in it?
  4. Drug list. Is each of your prescriptions still covered, at what tier, and with any new prior-authorization or step-therapy rule?
  5. Accounts. What will the employer put into an HSA or HRA, and what are the new HSA and FSA limits?

Step 3: verify the network yourself

A directory listing is a starting point, not proof. For each provider who matters to you, call their office and ask whether they will be in network next year for the exact plan name you are considering. Then confirm with the insurer, and write down the date and the name of the person you spoke to. Pay special attention to the hospital you would use in an emergency and to any specialist you see regularly. If a planned procedure is coming, ask about everyone who will bill for it, not just the surgeon, and ask whether the plan requires prior authorization.

Step 4: compare total cost, not premium

For every plan open to you, compute the three years from chapter 2: a quiet year, the year you expect, and a bad year at the out-of-pocket maximum. Include the employer's HSA deposit and the tax value of any HSA or FSA money. The HDHP vs PPO calculator does this across a range of care costs.

If you buy on the Marketplace, update your income estimate before comparing: the premium tax credit, and whether you are near the 400% line, can change the answer more than any plan feature. Chapter 5 and the ACA subsidy calculator cover this. If you are on Medicare, run your exact drug list through the Medicare Plan Finder every year, since Part D plans change formularies and prices annually.

Choose the plan that does best across the three years and still covers your doctors and drugs. If two plans are close, prefer the one with the lower out-of-pocket maximum: it protects you in the year you cannot predict.

Step 5: set next year's accounts

Enrollment is also when you set pre-tax amounts, and at most employers they do not roll over automatically.

  • HSA: decide the payroll amount so that yours plus your employer's reaches what you can afford up to the limit (chapter 3).
  • Health FSA: elect what you are nearly certain to spend, using step 1 (chapter 4).
  • Dependent care FSA: re-elect if you will have qualifying childcare costs.
  • Receipts: start next year's folder.

Keep track during the year

The review is easier when the year's records already exist. Each time an Explanation of Benefits arrives, check it against any bill before paying, as chapter 6 explains, and file both. Keep a simple running log: date, provider, what the plan paid, what you paid, and from which account. It tells you, at a glance, how close you are to the deductible, which helps time elective care in a year when you have already reached it, and it is the first page of next year's review.

Events that should trigger a review now

Some changes cannot wait for the fall. Each of these usually opens a special enrollment period, and the deadline is short: generally 30 days for an employer plan and 60 days on the Marketplace.

  • marriage, divorce, or a birth or adoption
  • losing other coverage, including a job loss or a child turning 26 on a parent's plan
  • a move to a new area with different plans
  • a large change in income if you buy on the Marketplace, so the advance credit can be adjusted (report it promptly; a change that alters what help you qualify for can also let you change plans)
  • turning 65, or approaching Medicare while still working (chapter 7)

A new diagnosis does not open an enrollment window, but it is a reason to check your plan's rules for the care you now need and to plan for the next open enrollment.

YOUR NEXT STEPSDo this now
  1. Put next year's open enrollment window for your coverage in your calendar, with a reminder two weeks before it opens.
  2. Download this year's claims and total your premiums and care costs, so step 1 is done before the window opens.
  3. List the providers and prescriptions you must keep, ready to check against next year's network and drug list.
  4. When next year's plan details arrive, run each option through the HDHP vs PPO calculator and reset your HSA and FSA amounts.

This chapter offers a general routine for reviewing coverage under 2026 rules. It is not personal financial advice; the plans available to you and their documents decide what is best for you.

KEY TERMS
ACA premium tax creditOut-of-pocket maximumHealth flexible spending account (FSA)
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