Financial Planning
Navigating Health Insurance Enrollment Season
October 27, 2026 · 5 min read
As fall gets into full swing, financial decision-making is probably not top of mind. You may be more accustomed to planning around deadlines such as Dec. 31 or April 15. But fall is an important time to take a fresh look at your health insurance.
For Affordable Care Act (ACA) Marketplace plans through HealthCare.gov, open enrollment runs from Nov. 1 through Jan. 15. Enroll by Dec. 15 for coverage beginning Jan. 1; later enrollment generally means coverage begins Feb. 1. State-run Marketplace deadlines may differ. Meanwhile, employer plans have their own enrollment periods, which may occur at different times, but frequently in the fall as well.
If you buy coverage through the Marketplace, keep in mind that the enhanced premium tax credits available from 2021 through 2025 have expired, and as of this writing Congress has not renewed them. Your after-subsidy premium may be noticeably higher than you remember, which makes comparing plans this year all the more worthwhile.
If you are approaching age 65, see our guide to preparing for Medicare for a separate look at enrollment considerations.
Faced with a long list of plans and prices, it can be tempting to stick with the devil you know and re-enroll in your current plan—done! But plan details change every year, and so do your needs. Consider taking a few minutes to review the options available. Here are some things to keep in mind.
Considering Total Annual Costs
A common mistake when choosing a health insurance plan is basing the decision solely on the monthly premium. That's understandable: The premium is a bill—or a deduction from your paycheck—you need to pay every month, even if you only see a doctor once a year for a checkup. But your actual costs may depend on several factors. Consider also:
- The deductible. What you generally pay for covered healthcare services before your insurance begins to pay. Some services may be covered before you meet the deductible. A higher deductible often comes with a lower monthly premium.
- Copays. A fixed amount you pay for a covered healthcare service, such as a doctor's visit or prescription. Specialist visits can cost more than visits to your primary care physician.
- Coinsurance. The percentage of the cost of a covered service that you pay after meeting your deductible.
- Doctor and hospital networks. Insurers contract with providers in their networks to negotiate prices. Out-of-network visits can cost more—or may not be covered at all. Make sure your preferred doctors are in the plan's network.
- Out-of-pocket maximum. The most you'll pay during a plan year for covered, in-network healthcare services. Your out-of-pocket maximum is frequently higher than your deductible. Once you reach the limit, your plan generally pays 100% of the cost of covered, in-network services for the rest of the plan year. Premiums, out-of-network care and services the plan doesn't cover generally don't count toward the limit.
- Prescription-drug coverage. Plans have lists of covered drugs, known as formularies. Prescription costs usually have their own copays and coinsurance, depending on the drug's "tier" or price level. If you take regular medications, make sure they're covered by the plan.
- HSA eligibility. Health Savings Accounts are tax-advantaged accounts that let you save, grow and spend money tax-free for qualified medical expenses. However, they generally must be paired with a high-deductible health plan. That said, certain Bronze and Catastrophic Marketplace plans are now treated as HSA-compatible under IRS rules.
Ultimately, choosing a plan is a balancing act: weighing the up-front premium against potential medical expenses down the road. If you're young and in good health, a high-deductible plan with a lower premium might make sense, given the statistical likelihood that you won't need major medical care in a given year.
But someone with ongoing healthcare needs might be better off paying a higher monthly premium in exchange for a lower deductible and out-of-pocket maximum. A plan with a $500 monthly premium saves $3,000 a year compared with one costing $750. Weigh those savings against differences in deductibles, coinsurance and out-of-pocket limits.
Changing Plans Midstream: Special Considerations
America's employer-based health insurance system can leave people uncovered during job transitions, prompting special exceptions to the open enrollment period. Under COBRA, you can continue coverage on your previous employer's plan for a limited time—but you'll pay the full monthly premium plus a 2% administrative fee because your former employer no longer contributes its share.
For many people, another option is buying a plan through the ACA Marketplace. Losing employer-based health coverage generally triggers a special enrollment period, giving you 60 days after losing coverage to enroll. In many cases, you can also enroll during the 60 days before your coverage ends. When your new employer-sponsored insurance begins, you can cancel the Marketplace plan or decide to keep it. An offer of employer coverage that meets affordability and minimum-value requirements generally makes you ineligible for Marketplace premium tax credits, even if you decline that coverage.
If you're applying for a subsidy, be sure to factor in your total income from both jobs when estimating your eligibility. If your actual income is higher than estimated, you could receive more financial assistance than you're ultimately eligible for, so you may have to repay the full difference when you file your federal tax return.
Also, speaking of owing the government money: If you're joining a new employer's plan that automatically contributes to a health savings account (HSA), make sure those contributions, plus contributions you or a previous employer made this year, won't push you over the annual contribution limit. In 2026, the annual contribution limit for HSAs for an individual with self-only coverage is $4,400 and $8,750 for family coverage. These limits apply to total contributions across all your HSA accounts. If you are married, family HSA limits apply to spouses' combined accounts. Eligible individuals age 55 or older can contribute an additional $1,000; each spouse must make any catch-up contribution to their own HSA.
A job change is also a useful time to review whether to consolidate retirement accounts.
A Yearly Checkup for Your Health Coverage
Open enrollment gives you a chance to make sure your health insurance still fits your needs. Take time to compare premiums, deductibles, provider networks, prescription coverage and potential out-of-pocket costs before making a decision. For those nearing retirement, healthcare costs also belong in your retirement income plan.
This can be a lot of work. But we're here to help. Reach out if you need help evaluating how your options fit into your budget or broader financial plan.
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Data sources for returns and standard statistical data are provided by the sources referenced and are based on data obtained from recognized statistical services or other sources we believe to be reliable. However, some or all information has not been verified prior to the analysis, and we do not make any representations as to its accuracy or completeness. Any analysis nonfactual in nature constitutes only current opinions, which are subject to change. Benchmarks or indices are included for information purposes only to reflect the current market environment; no index is a directly tradable investment. There may be instances when consultant opinions regarding any fundamental or quantitative analysis do not agree.
The commentary contained herein has been compiled by W. Reid Culp, III from sources provided by TAGStone Capital, as well as commentary provided by Mr. Culp, personally, and information independently obtained by Mr. Culp. The pronoun "we," as used herein, references collectively the sources noted above.
TAGStone Capital, Inc. provides this update to convey general information about market conditions and not for the purpose of providing investment advice. Investment in any of the companies or sectors mentioned herein may not be appropriate for you. You should consult your advisor from TAGStone for investment advice regarding your own situation.
TAGStone Capital, Inc. does not provide tax, legal or insurance advice. Health plan options, costs and deadlines vary by state and employer — please consult your plan administrator, HealthCare.gov or a qualified tax professional regarding your particular circumstances.
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