Open Enrollment Guide 2027: Benefits Checklist
Tiffany Rosetti, Senior Vice President, Financial Advisor
CFP®, CEPA®, BFA ·
Sandy Springs Team ·
Oct 6, 2026
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Key Dates:
- ACA Health Insurance Marketplace: November 1 through January 15
- Medicare Annual Enrollment Period: October 15 through December 7
- Employer-sponsored plans enrollment: Typically, 2 to 4 weeks in the fall; check with your HR department
Open enrollment is the annual window to review, select, or change workplace benefits and health insurance. While this is crucial for your health savings plan, open enrollment can also impact your retirement savings, tax-advantaged accounts, and overall financial planning.
What Is Open Enrollment, and Why Does It Matter?
During open enrollment, employer-sponsored benefits, Medicare, and ACA Marketplace plans can be changed. Open enrollment is the only annual window to make changes to your workplace benefits and health insurance. Other than qualifying life events, health benefits cannot be changed after open enrollment. Health coverage, retirement contributions, tax savings, and insurance protection are all set during this period.
Open Enrollment Dates and Deadlines for 2027
ACA Health Insurance Marketplace Dates
- The Federal marketplace has open enrollment from November 1 through January 15.
- If you want coverage to start on January 1, you will need to meet the December 15 deadline.
- Some states run their own exchanges with different deadlines.
- For more information on Marketplace click here.
Medicare Enrollment Periods
- The Annual Enrollment Period (AEP) runs October 15 through December 7.
- Medicare Advantage Open Enrollment Period runs January 1 through March 31.
- For those turning 65 in 2027, the Initial Enrollment Period allows you to apply for Medicare over the span of seven months. You can apply for Medicare at any time between three months before your birthday and three months after your birthday.
Employer-Sponsored Benefits
- Typically, open enrollment is available for two to four weeks in September through November.
- To figure out when your company has open enrollment, contact your benefits department.
How to Choose the Right Health Insurance Plan
Understanding Plan Types at a Glance
| Plan Type | Premiums | Deductibles | Network Availability |
|---|---|---|---|
| HMO | Low premiums | Low cost or no deductible option | Requires using health care within network with greater restrictions than other plans |
| PPO | Premiums tend to be higher | Plans often come with a deductible | Often, out-of-network care is allowed, but there may be higher costs than in-network care |
| EPO | Offers lower premiums | Likely has a higher deductible | Often do not offer out-of-care benefits |
| POS | Higher premiums than HMOs but lower than PPOs | Can have higher deductibles | Offer some out-of-care coverage but may have a higher copay |
| HDHP | Depends on plan type
HDHPs can be any type of plan as long as it reaches the deductible limit | Have deductibles that are above the HDHP limit, regardless of other plan type | Depends on plan type |
| Plan Type | Pros | Cons | Best For |
|---|---|---|---|
| HMO | A more affordable health insurance option | Does not offer much flexibility
Requires a primary care physician to refer you to other network providers as needed | Value |
| PPO | Offers more flexibility | Can lead to higher costs
More likely to need preapprovals on medical care | A mix of flexibility and cost |
| EPO | Does not require a primary care physician or referrals | Less options | If you prefer specialist care |
| POS | Allows greater flexibility than other plans while not being too costly | Requires referrals to see specialists | If you need a plan that has aspects of HMOs and PPOs |
| HDHP | Offers lower premium
Offers HSA eligibility | Can be a higher out-of-pocket expense | HSA eligibility
|
The best health insurance for you will depend on your own financial goals. Compare premiums, deductibles, copays, coinsurance, and out-of-pocket maximums before deciding on which plan to enroll in. Check with your employer about possible healthcare benefits directly connected to insurance.
HSA-Eligible Plans and Health Savings Accounts
To apply for a Health Savings Account (HSA), you must have an HDHP. In 2027, your HDHP must have a minimum deductible of $1,750 for individual plans or $3,500 for family plans. HSAs offer a triple tax advantage: Tax-deductible contributions, tax-free growth, and tax-free withdrawals for qualified medical expenses.
FSA, HRA, and Other Healthcare Accounts
If you are not eligible for an HSA, there are other healthcare accounts available.
- Flexible Spending Accounts (FSAs) also provide tax-free withdrawals but have a use-it-or-lose-it rule attached.
- Health Reimbursement Arrangements offer some covered costs for eligible health expenses.
- Limited-purpose FSAs cover dental and vision care and can be paired with HSAs.
Maximizing Retirement Plan Contributions
Employer-sponsored plans go beyond healthcare; they can also offer meaningful retirement plan contributions.
401(k), 403(b), and 457(b) Contribution Limits
While the 2027 limits have not been announced yet, open enrollment is a key time to review and elect employer-sponsored retirement plans. Depending on your sector, your employer may offer a 401(k), 403(b), or a 457(b).
In 2026, the base employee deferral limit is $24,500, with a catch-up limit of $8,000 for those 50+, and a super catch-up limit of $11,250 for ages 60-63. Some employers will offer a contribution match, up to a certain amount. When planning your contributions, use the employer match to your advantage.
Roth vs. Traditional Contributions
Both Roth and Traditional IRAs offer tax-free growth and a chance to increase your retirement funds. In a Roth IRA, expenses are distributed after tax but then grow tax-free and are withdrawn tax-free for eligible purchases. In a Traditional IRA, contributions are made pre-tax and grow tax-free but are taxed at the time of withdrawal.
Under the One Big Beautiful Bill Act (OBBBA), to qualify for a Roth IRA, you must have a MAGI under $153,000 for single filers or under $242,000 for joint filers. Beyond income limits, whether a Roth IRA or a Traditional IRA is right for you depends on your tax situation, overall retirement plan, and the possibility of using Roth conversions.
Deferred Compensation Plans
Deferred compensation allows you to earn income now but be paid later. While qualified deferred compensation can include retirement plans such as 401(k)s, non-qualified deferred compensation plans can be offered to high-earning employees and executives.
Non-qualified deferred compensation can help decrease tax risk, but they offer less protection in the case of creditors. Open enrollment can be a prime time to review and select your deferred compensation plan, if offered.
Tax-Smart Moves to Make During Open Enrollment
- Review how your benefits elections affect your taxable income.
- Coordinate HSA/FSA elections with your broader tax strategy
- Consider the OBBBA’s impact on SALT deductions, QBI, and retirement planning.
Life Insurance and Disability Coverage Review
Group Life Insurance
In some cases, employers may provide life insurance coverage. These group life insurance plans usually cover all eligible employees under one contract. You typically do not need to pay premiums for group life insurance.
Supplemental life insurance can be added to group life insurance plans, giving you more coverage. Although you will be responsible for premiums, supplemental life insurance is often cheaper than if you were not paying through your employer.
During open enrollment, consider whether supplemental life insurance is right for you. Consider increasing coverage if you have recently gotten married, have welcomed a new child, or if there have been significant additions to your estate.
Disability Insurance
Disability insurance will depend on whether you are covering for a short-term or long-term disability. Employer coverage may not be sufficient for repeated years of costs. During open enrollment, review your employer’s disability insurance coverage and determine which plan is right for you.
Beneficiary Designations and Estate Planning
During open enrollment, your retirement accounts and life insurance may change. Regardless of updates to your plan, open enrollment presents a convenient time to review beneficiary designations.
If you have updated your retirement accounts or life insurance, you must also update beneficiary designations to ensure each asset has a beneficiary. Make sure no beneficiaries are outdated after divorce, remarriage, or death.
What Happens If You Miss Open Enrollment?
Qualifying Life Events and Special Enrollment Periods
Certain qualifying life events will allow you to change coverage. Qualifying events include:
- Marriage
- Birth/adoption
- Job loss
- Loss of other coverage
- Turning 26
- Moving
After a qualifying event, you typically have 30 to 60 days to make any changes.
Employer plans may also have special enrollment periods. Check with your company’s benefits department to see when adjustments can be made.
Fallback Options
If you miss open enrollment and are unable to make any changes, there are several fallback options. Specific fallback options for health insurance include:
- COBRA coverage (expensive but available)
- Short-term health insurance with limitations
- Medicaid and CHIP
Your Open Enrollment Checklist
- Review last year’s healthcare spending and usage
- Compare plan options side by side (do not auto-renew without reviewing)
- Verify your doctors and prescriptions are in-network
- Update retirement contribution rates to maximize employer match
- Evaluate Roth vs. Traditional contribution allocation
- Review HSA/FSA election amounts based on anticipated medical expenses
- Update beneficiary designations on all accounts
- Review life insurance and disability coverage needs
- Set a deadline to complete elections before the enrollment window closes
- Schedule a financial planning review with an advisor
Make Open Enrollment Count with Expert Guidance
Open enrollment is a meaningful time to update essential parts of your financial plan. The window affects taxes, retirement savings, insurance, and estate planning. While this may sound overwhelming, you do not need to go through open enrollment alone. Request a meeting with an advisor at Wealth Enhancement today to create a meaningful financial plan.
Frequently Asked Questions About Open Enrollment
Has open enrollment been extended for 2027?
For 2027 plans, ACA marketplace will be open from November 1 to January 15. The Medicare Annual Enrollment Period will be open from October 15 through December 7. Employer-sponsored plans vary but are typically open for 2 to 4 weeks in the fall. For more specific dates, consult with your HR department.
What happens if I do not enroll during open enrollment?
If you do not enroll during open enrollment, plans will become limited. The only time you will be able to change your enrollment is during qualifying life events. However, there are still some SEP options available outside of the open enrollment period.
Can I change my health insurance outside of open enrollment?
It depends. Health insurance usually cannot be changed outside of open enrollment except in the case of qualifying life events. Qualifying life events include marriage, a new child, job loss, loss of other coverage, turning 26, or moving.
How much should I contribute to my 401(k) during open enrollment?
How much you should contribute depends on your overall financial goals. However, it is important to contribute enough to take advantage of your employer match. Pay attention to 401(k) limits and determine if front-loading is the strategy right for you.
Should I choose an HSA or FSA during open enrollment?
HSAs and FSAs have unique advantages and disadvantages. HSAs require a high-deductible health plan (HDHP), although they often have more flexibility. FSAs allow you to use funds immediately but have a use-it-or-lose-it stipulation. The plan that is right for you depends on overall medical expenses, employer offering, and if you can afford HSA fees.
Content in this material is for general information only and not intended to provide specific advice or recommendations for any individual. This article was originally published on 11/18/2023 and has been updated.
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About the author
Senior Vice President, Financial Advisor
CFP®, CEPA®, BFA
Tiffany Rosetti works with high net worth and ultra high net worth families, business owners, and executives seeking clarity and confidence in complex financial decisions. Since entering the wealth management industry in 2007, she has advised multigenerational families through…
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