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Most employer open enrollment windows run from October through mid-November, with changes taking effect January 1, 2027. The decisions you make in this 2-4 week window lock in your health coverage and flexible spending for the entire next year. Most people spend less than 30 minutes on open enrollment and accept whatever they had last year. Here is how to spend 60 minutes and potentially save $1,000-$3,000.
The Biggest Mistake: Auto-Renewing Without Reviewing
Auto-renewing last year’s plan is convenient but often costly. Plans change every year — premiums increase, networks narrow, formularies change, and deductibles shift. The plan that was optimal last year may not be optimal this year. Spending 30 extra minutes comparing your options is worth it.
Step 1: Estimate Your Healthcare Usage for Next Year
Before comparing plans, estimate how much healthcare you realistically expect to use next year:
- How many primary care visits per year (average: 2-3)?
- Do you have any specialist visits, ongoing prescriptions, or planned procedures?
- Any major life events coming up — pregnancy, surgery, starting a family?
This estimate determines whether a low-premium/high-deductible plan or a higher-premium/lower-deductible plan makes financial sense for your situation.
Step 2: Calculate the True Annual Cost of Each Plan
Never compare plans by monthly premium alone. The true annual cost is:
Annual premium + expected out-of-pocket costs = true annual cost
Example with two plans for a healthy person with 3 doctor visits and 1 prescription per year:
| Plan A (PPO) | Plan B (HDHP) | |
|---|---|---|
| Monthly premium | $280 | $140 |
| Annual premium | $3,360 | $1,680 |
| Deductible | $500 | $2,800 |
| Expected out-of-pocket (3 visits + Rx) | ~$300 | ~$400 |
| True annual cost | $3,660 | $2,080 |
| HSA tax savings (HDHP only) | N/A | -$946 (22% bracket, $4,300 contribution) |
| Net annual cost | $3,660 | $1,134 |
For a healthy person, the HDHP saves over $2,500 per year when HSA tax savings are factored in. The math flips for someone with high medical utilization.
Step 3: The HDHP + HSA Decision
If your employer offers a High Deductible Health Plan paired with an HSA, this combination deserves serious consideration for anyone who is generally healthy. The 2026 HSA changes expanded eligible expenses significantly. The triple tax advantage — pre-tax contributions, tax-free growth, tax-free withdrawals for medical expenses — makes the HDHP+HSA one of the best financial tools available.
The risk: if you have a major medical event in a year with an HDHP, you pay a higher deductible before insurance kicks in. Mitigate this by funding your HSA to cover the full deductible amount ($2,800-$3,200 for most individual HDHPs) before spending it on routine care. Treat the HSA as a medical emergency fund first, investment account second.
Step 4: Check Your Prescriptions Are Covered
If you take regular medications, verify that each prescription is on the plan’s formulary (covered drug list) and at what tier (tier 1 is cheapest, tier 4-5 is most expensive). A plan with a lower premium but your medication at tier 4 may cost more annually than a plan with a slightly higher premium and your medication at tier 2.
Check formularies on the insurance company’s website or your employer’s benefits portal before open enrollment closes.
Step 5: Verify Your Doctors Are In-Network
If you have preferred doctors or specialists you see regularly, confirm they are in-network under any plan you are considering. An out-of-network specialist visit can cost 2-5x more than the same visit in-network, negating premium savings quickly.
Other Benefits to Review During Open Enrollment
Dental and vision: Often underutilized. If you need dental work or new glasses, confirm the plan covers your anticipated needs before the year begins.
FSA elections: Healthcare FSA allows pre-tax contributions for medical expenses. The 2026 limit is $3,300. Unlike HSAs, FSAs are use-it-or-lose-it — elect only what you will spend.
Dependent Care FSA: The 2026 limit increased to $7,500 for married filing jointly under the OBBBA. If you have childcare costs, maximizing this benefit saves $1,650-$1,800 in federal taxes alone. See our full Dependent Care FSA guide.
Life and disability insurance: Most employers offer supplemental coverage during open enrollment without medical underwriting — meaning you can increase coverage without a health exam. If you have dependents or significant debt, review whether current coverage is adequate.
Key Dates
- Employer open enrollment: Typically October 1 – November 15, 2026 (varies by employer)
- ACA Marketplace open enrollment: November 1 – January 15, 2027
- Changes effective: January 1, 2027
This article is for informational purposes only and does not constitute health insurance or financial advice. Plan details vary by employer and insurer.
