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Fall Open Enrollment Arrives for Health Insurance and Employee Benefits – What You Need to Know

October 31, 2026•2 min read

November 1, 2026

Annual open enrollment periods make November a critical month for household tax and budget planning. Here are some reminders to help you make the right moves.

Expanded HSA Eligibility and 2027 HSA/FSA Contribution Limits

Health savings accounts (HSAs) offer a rare triple federal tax advantage: tax-shielded contributions, tax-free growth, and tax-free withdrawals for qualifying healthcare costs. Generally, you may only contribute to an HSA if you carry health insurance classified as a high-deductible health plan (HDHP). A federal law enacted in 2025 expanded HSA eligibility beginning January 1, 2026, by treating qualifying bronze-level and catastrophic insurance plans as HDHPs. Other HSA eligibility requirements still apply. The annual HSA contribution limit increases to $4,500 in 2027 for self-only coverage, and $9,000 for family coverage.

The employee contribution limit for health flexible spending arrangements (FSAs) is projected to rise to $3,500 in 2027, pending IRS confirmation. Remember that a yearly “use it or lose it” rule generally applies to FSAs, although your employer’s plan may allow a limited carryover or a grace period. It does not make sense to contribute significantly more to your account than you expect to need for eligible expenses. By contrast, you may leave funds in an HSA indefinitely without penalty.

Health Insurance Marketplace Enrollment Deadlines & New Restrictions

If you purchase your own health insurance because you cannot get affordable coverage through a workplace, then you may qualify for the Premium Tax Credit. To receive the credit, which may be taken as a reduction in monthly premiums, you must purchase your plan through the Insurance Marketplace, also called the Exchanges. For HealthCare.gov, the open enrollment period runs from November 1, 2026, through January 15, 2027. You generally must enroll by December 15, 2026, and pay any required first premium to have coverage starting January 1, 2027. State Marketplace deadlines may differ. Review your Marketplace renewal notice carefully, update your expected income and household information, and promptly submit any documents requested to verify your eligibility for coverage or financial assistance. Starting the signup process as early as possible can help prevent coverage delays.

Employer Contributions to 529 Plans and Trump Accounts

As in the past, employers may contribute to an employee’s Section 529 tuition savings plan in 2027. There is no uniform federal annual contribution limit, but contributions are subject to the plan’s aggregate limits. Employer contributions generally count as taxable income for the employee.

Employers that establish a qualifying Trump Account contribution program may also contribute to Trump Accounts for employees’ dependent children. If the program includes a qualifying cafeteria plan arrangement, employees may contribute through paycheck reductions. In 2027, a combined total of up to $2,500 in employer-funded and qualifying paycheck-reduction contributions may be excluded from an employee’s federal taxable income. This limit applies per employee across eligible accounts, not separately for each child. These contributions generally remain subject to Social Security and Medicare taxes (FICA). All workplace contributions count toward the Trump Account annual contribution limit of $5,000 per beneficiary.

Expanded HSA Eligibility2027 HSA/FSA ContributionHealth Insurance Marketplace Enrollment Deadlines & New Restrictions529 PlansTrump Accounts
Diva R. Mejias

Diva R. Mejias

Diva R. Mejias is a seasoned professional with over three decades in corporate finance, including a notable role as District Controller for United Parcel Service where she managed $350M annually. An entrepreneur with significant tax expertise, she's a Main Street Certified Tax Advisor and ITIN Certified Acceptance Agent, preparing thousands of tax returns under her company, DM Financial Services. Additionally, she is licensed in multiple states as an insurance agent and serves as a Realtor with CENTURY21. Diva has also lent her expertise to numerous non-profits and currently holds several board positions. She's been recognized for her work and community service, receiving awards such as the 2021 Bloc 50 over 50 and the 2023 Annual Tribute to Women.

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