Healthcare planning is a key part of year-end financial preparation. Many healthcare-related decisions follow strict timelines that align with the calendar year, and missing these deadlines may limit the options you have available until the next enrollment period. Give yourself time to review your current coverage, evaluate your account balances and prepare for upcoming enrollment windows.
This article outlines the main healthcare deadlines and tasks to review, including open enrollment periods, Health Savings Accounts (HSAs), Flexible Spending Accounts (FSAs) and Medicare-related decisions. Each of these areas is governed by rules set by federal agencies, such as the Internal Revenue Service (IRS) and the Centers for Medicare & Medicaid Services (CMS).
Reviewing Coverage Ahead of Open Enrollment
Open enrollment is the main period when you could select or change your health insurance coverage. For employer-sponsored plans, open enrollment is usually in the fall, although the exact timing may vary by employer. Reviewing your current coverage before enrollment begins gives you time to compare your plan options and understand any changes in premiums, deductibles or provider networks.
For people who obtain coverage through the federal marketplace, open enrollment generally begins in November and continues into January¹. Changes made during this period usually take effect at the start of the next year. Because plan details may change annually, reviewing available options each fall remains an important step.
Early preparation allows you to gather information about expected healthcare needs, including prescriptions, routine care and any anticipated procedures. This may be helpful when comparing plan features during enrollment.
Understanding Medicare Enrollment Periods
Medicare follows a set schedule for enrollment and plan changes. The Medicare Open Enrollment Period runs each year from October 15 through December 7². During this time, those enrolled in Medicare could review and adjust their coverage, including Medicare Advantage plans and prescription drug plans.
Changes made during this period generally take effect on January 1 of the following year. Because plan costs, covered medications, and provider networks may change, reviewing these details annually is part of maintaining current coverage.
Along with the annual open enrollment period, some people may qualify for special enrollment periods based on specific life events, like moving or losing other coverage. But these situations are limited, and most changes must be made during the standard enrollment window. Reviewing your Medicare options in early fall gives you time to compare plans and confirm your current coverage continues to address your healthcare needs.
Evaluating Health Savings Accounts (HSAs)
HSAs are tax-advantaged accounts available to people who are enrolled in eligible high-deductible health plans. Contributions to HSAs may be tax-deductible, and funds may be used for qualified medical expenses.
The IRS sets annual contribution limits for HSAs and adjusts them periodically³. While contributions for a given tax year may generally be made until the tax filing deadline of the next year, reviewing contributions in early fall allows time to plan for any remaining contributions before year-end.
Eligibility for HSA contributions depends on whether you're enrolled in a qualifying high-deductible health plan. Unlike flexible spending accounts, unused HSA funds typically carry over from year to year. This makes HSAs a longer-term planning tool, but annual contribution limits still apply.
Managing Flexible Spending Accounts (FSAs)
FSAs are commonly offered through employer-sponsored benefit plans. These accounts allow individuals to set aside pre-tax funds for eligible medical or dependent care expenses.
Many FSAs operate under a “use-it-or-lose-it” rule, meaning funds must be used within the plan year unless the employer offers a grace period or limited carryover option⁴. Because of this structure, reviewing FSA balances is an important step.
Eligible expenses may include medical visits, prescription medications and certain dependent care costs. Planning ahead gives you time to schedule appointments or make purchases that qualify under plan rules.
Tracking Healthcare Expenses and Documentation
Accurate recordkeeping is an important part of healthcare planning, particularly for individuals who may claim medical expenses as part of tax reporting. The IRS allows certain unreimbursed medical expenses to be deducted if they exceed a defined percentage of your adjusted gross income⁵.
Maintaining records of your healthcare expenses throughout the year supports this process. These records may include receipts, invoices and insurance statements that show out-of-pocket costs. Review these records and make sure that all documentation is complete. This step may also help identify any additional eligible expenses that could be incurred before year-end.
Planning for Prescription Coverage and Provider Networks
Healthcare plans often change from year to year, including updates to prescription drug formularies and provider networks. These changes may affect access to medications or healthcare providers. Reviewing current prescriptions and provider relationships ahead of open enrollment allows you to confirm whether your existing plan continues to address your needs. If changes are identified, open enrollment allows you to select a plan that might include preferred providers or medications.
Preparing for Year-End Deadlines
Many healthcare-related actions are tied to the end of the calendar year. FSA funds may need to be used by December 31, depending on plan rules, and certain enrollment decisions must be completed within defined timeframes.
Increased activity during the final months of the year may also affect scheduling availability for medical appointments. Allow yourself time to schedule visits and complete eligible expenses before deadlines.
Coordinating Healthcare Planning with Other Financial Areas
Healthcare decisions often connect with other aspects of financial planning. Contributions to HSAs and FSAs may affect taxable income, while medical expenses may be relevant for tax reporting. Reviewing healthcare planning alongside other year-end financial activities, such as tax preparation and charitable giving, provides a more complete view of your overall financial activity.
Working with a Financial Professional
Healthcare planning may involve reviewing multiple factors, including insurance coverage, account contributions and potential tax considerations. Working with a financial professional may support a more comprehensive review of these elements.
Scheduling a review to evaluate current coverage, confirm deadlines and address any outstanding items before the end of the year. This timing may also provide flexibility in making any necessary changes.
Conclusion
Healthcare deadlines and tasks play a major role in your year-end financial planning. Open enrollment periods, account contribution limits and expense deadlines all follow defined schedules that require advance attention. If you're ready to start preparing for your year-end deadlines, get in touch with a financial professional today.
Important Disclosures:
Content in this material is for educational and general information only and not intended to provide specific advice or recommendations for any individual. All information is believed to be from reliable sources; however, LPL Financial makes no representation as to its completeness or accuracy. This article was prepared by WriterAccess. LPL Tracking #1155965-04
Footnotes
1Open Enrollment Period https://www.healthcare.gov/glossary/open-enrollment-period/
2Medicare Open Enrollment https://www.cms.gov/priorities/key-initiatives/medicare-open-enrollment-partner-resources
3Publication 969 (2025), Health Savings Accounts and Other Tax-Favored Health Plans https://www.irs.gov/publications/p969
4Health Savings Accounts and Other Tax-Favored Health Plans https://www.irs.gov/pub/irs-pdf/p969.pdf
5Topic no. 502, Medical and dental expenses https://www.irs.gov/taxtopics/tc502