Dropbox Employees: Save on Health Care Taxes with the 2026 HSA Expansion

Healthcare Provider Update: Offers health insurance through Anthem PPO/HSA and Kaiser HMO (CA & HI), plus dental and vision via Guardian 3. As ACA premiums surge, Dropboxs comprehensive coverage and employer-paid options help employees avoid steep out-of-pocket costs expected in the marketplace. Click here to learn more

'With the 2026 expansion of HSA eligibility, Dropbox employees have a rare opportunity to integrate tax-advantaged health care savings into long-term retirement planning, turning modest contributions into meaningful, tax-favored reserves.' – Wesley Boudreaux, a representative of The Retirement Group, a division of Wealth Enhancement.

'Dropbox employees can leverage the expanded HSA rules in 2026 to build a versatile, tax-advantaged reserve for future health care costs, complementing their broader retirement strategy.' – Patrick Ray, a representative of The Retirement Group, a division of Wealth Enhancement.

In this article, we will cover:

1. The expansion of Health Savings Account (HSA) eligibility in 2026.

2. The triple tax advantages that HSAs offer.

3. How Dropbox employees can incorporate HSAs into long-term retirement planning

By Kevin Won, Wealth Enhancement advisor

Health Savings Accounts Are Expanded: Millions More May Qualify in 2026

Thanks to a key change in tax law, an estimated 10 million more Americans may qualify for Health Savings Accounts (HSAs) starting in 2026. ¹  For eligible employees at Dropbox, this could represent a major chance to manage taxes while building long-term health care reserves.

Kevin Won, an advisor at Wealth Enhancement, describes this as “one of the most underused yet effective ways to mitigate taxes while planning for health care costs in retirement.” He further notes that many more households will now have access to powerful solutions for growing tax-favored savings that support long-term goals.

How HSAs Work

For eligible medical expenses, HSAs function as tax-advantaged accounts. Because contributions are made before taxes, taxable income is reduced immediately. After funding, account balances may be invested and grow without yearly tax drag. A triple benefit emerges when qualified medical withdrawals are made, as those withdrawals are not taxed. Dropbox employees may find these features especially compelling, because unused balances carry forward indefinitely, somewhat like a 401(k).

What Changes in 2026

Under current rules, only individuals in high-deductible health plans (HDHPs) are eligible for HSAs. As of January 1, 2026, however, certain policies purchased through the Affordable Care Act's marketplace and other insurance plans will also be eligible. Specifically, it will become possible to pair HSAs with marketplace bronze plans and catastrophic plans, which will be treated as HDHPs going forward. ²  For Dropbox retirees, this shift may open new possibilities that were previously closed. The updated law offers an additional way to enhance tax efficiency and plan for future medical costs.

The Triple Tax Advantage

Won outlines three core benefits of HSAs:

1. Contributions are deductible, which lowers taxable income upon deposit.

2. Investments grow on a tax-free basis.

3. Withdrawals for eligible health costs are untaxed.

Thanks to these features, HSAs offer a tax-efficient way to save for health care costs. After age 65, HSA funds can even be used for non-medical expenses, although withdrawals for those purposes are taxable. ³  This allows Dropbox employees to use them like a supplemental retirement pool to address medical costs or to provide additional income when used strategically. 

Bottom Line

For millions of Americans, the expanded eligibility in 2026 is a strong opportunity to manage taxes and plan for medical expenses more effectively. “The earlier you begin, the greater the compounding effect,” Won stated. Over time, even modest contributions can accumulate into significant tax-free funds.

In 2026, the annual contribution limit for HSAs will rise to $4,400 for single plans and $8,750 for family coverage. ⁴  For those age 55 and older, the $1,000 annual HSA catch-up contribution will also remain in 2026, permitting larger tax-favored deposits. For Dropbox employees nearing retirement, that extra buffer may be especially helpful in offsetting rising health care costs.

A Final Analogy

Imagine an HSA as planting a resilient oak tree in your financial landscape. Each contribution is a seed placed with tax perks, sheltered from erosion as it grows, and harvested tax-free when needed for medical costs. With the 2026 expansion, Dropbox employees now gain broader access to this fertile territory. By integrating HSAs into their broader retirement plans, participants can map contributions and growth, helping today’s modest seed grow into lasting tax-free shade for tomorrow’s health care needs.

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Articles you may find interesting:

Sources:

1. Barron's. ' More People Can Save Taxes on Health Expenses With These Accounts Under the New Law ,' by Karen Hube. 5 Oct. 2025.

2. KFF. ' Expansions to Health Savings Accounts in House Budget Reconciliation ,' by Meghan Salaga and Kaye Pestaina. 29 May 2025.

3. Fidelity Viewpoints. ' 5 Ways HSAs Can Help with Your Retirement. '  Fidelity , Sept. 2025. 

4. CNBC. ' IRS unveils new HSA limits for 2026, ' by Kate Dore. 2 May 2025.

Other Resources: 

1. Kiplinger Editors. 'Seven Things You Should Do Before 2026 Because of One Big Beautiful Bill Changes.'  Kiplinger , 3 Oct. 2025,  www.kiplinger.com/taxes/what-you-should-do-before-2026-because-of-obbba-changes

2. Morgan Stanley Wealth Management. 'HSAs: An Overlooked Retirement Savings Vehicle.'  Morgan Stanley , 17 Apr. 2024,  www.morganstanley.com/articles/health-savings-account-retirement-tax-advantages.

3. AARP Editors. 'HSA May Be Your Secret Tax Weapon for Retirement Saving.'  AARP , 10 Sept. 2025,  www.aarp.org/money/retirement/hsa-secret-tax-weapon/.