Don't Just Auto-Renew: A Self-Employed Health Insurance Check Before Open Enrollment

By Sandy Shao (邵贤弟), EA, CFA

If you buy your own health insurance, put November 1 on your calendar now. Open enrollment for 2027 coverage on Maryland Health Connection, Maryland's health insurance marketplace, runs from November 1, 2026 through January 15, 2027. This is your once-a-year window to change plans, and this year it matters more than usual.

Why this year is different

Maryland officials approved an average 14.6% premium increase for 2027 individual plans. That follows a 13.4% increase last year. This comes after the end of the enhanced federal premium tax credits in December 2025, which means less federal help offsetting rising health care and prescription drug costs.

If you simply let last year's plan roll over, you could pay a lot more for coverage that no longer fits your needs. About 274,000 Marylanders buy individual plans on the exchange, and state officials are urging them to shop their options rather than auto-renew.

MYTH: "Auto-renewing is the safe choice."

REALITY: Auto-renewing is the expensive choice this year. Your premium, your network, and your drug coverage may all have changed, even if your plan name stayed the same.

How to compare plans without getting lost

Compare four numbers, then do one simple piece of math.

• Monthly premium: what you pay every month.

• Deductible: what you pay out of pocket before the plan starts paying for most care.

• Out-of-pocket maximum: the most you would pay in a year for covered care.

• Network and prescriptions: whether your doctors are in network, and what your medicines cost.

Then estimate your total yearly cost: 12 months of premiums, plus what you would likely spend on care.

A plan with the lowest premium is not always the cheapest. If it has a high deductible and you need regular care, a higher-premium plan with a lower deductible can cost less over the full year.

Four carriers will offer 2027 plans on Maryland Health Connection: CareFirst, Kaiser Permanente, UnitedHealthcare, and Wellpoint Maryland. If you want coverage starting January 1, aim to enroll by mid-December to be safe, and confirm the exact cutoff on MarylandHealthConnection.gov.

The self-employed tax break many people miss

If you are self-employed, you may be able to deduct 100% of your health insurance premiums for yourself, your spouse, and your dependents. This above-the-line deduction lowers your income before the standard deduction, and you do not need to itemize to take it.

There are limits. For example, you generally cannot take this deduction if you were eligible for a subsidized plan through your spouse's employer, so check the rules for your household before you assume the full deduction.

Is an HSA right for you?

This is the part worth a second look this year, because the rules changed. A Health Savings Account (HSA) lets you set aside money tax-free for medical costs, and it grows and comes out tax-free for qualified medical expenses. To contribute, you must be enrolled in a qualifying high-deductible health plan (HDHP).

For 2027 coverage, the IRS limits are:

Coverage | HSA contribution limit | HDHP minimum deductible | HDHP out-of-pocket maximum

Self-only | $4,500 | $1,750 | $8,700

Family | $9,000 | $3,500 | $17,400

Catch-up contribution, age 55 and older: an extra $1,000.

Two recent changes make more people eligible than before.

First, all marketplace Bronze and Catastrophic plans are now treated as HDHPs for HSA purposes, even if they do not meet the dollar thresholds above. That means if you auto-renew a Bronze plan this year, you may be HSA-eligible for the first time without changing plans.

Second, direct primary care memberships no longer disqualify you, up to $150 a month for an individual or $300 a month for a family, and those fees can be paid tax-free from the HSA. Telehealth coverage before you meet your deductible also no longer kills HSA eligibility.

An HSA is not right for everyone. It works best if you can afford the higher deductible and fund the account. If you expect a planned surgery, take expensive medicines, or need frequent specialist visits, a lower-deductible plan may still be the better deal, even without an HSA.

What to do before November 1

• Check your renewal notice: your new premium, deductible, and drug costs for 2027.

• Confirm your doctors and medicines are still covered under the plan you are considering.

• Add up your likely total yearly cost, not just the monthly premium.

• If you are considering an HDHP, check whether it qualifies for an HSA, and whether you can fund one.

• If you had an HSA for 2026, remember you can still make 2026 contributions until April 15, 2027, under the 2026 limits.

• Gather your income estimate for 2027, since it affects any premium tax credit on the marketplace.

Open enrollment comes once a year, but the plan you pick affects every month of 2027. A one-hour comparison now can save real money in a year of double-digit premium increases.

Want help running the numbers for your business and household? Contact Ascend Tax & Advisory for a consultation.

This article is for educational purposes only and does not constitute tax advice. Tax laws are complex and change frequently. Please consult a qualified tax advisor about your own situation.