18 Oct Health Insurance & Medicare Enrollment Season Is Here

As summer winds down and autumn kicks into gear, I’m sure you’d rather be apple picking and pumpkin carving than making health-related financial decisions! But here we are.

We have two enrollment seasons running at the same time, and they follow different rules. Medicare’s annual enrollment period begins this week. Covered California, the state marketplace for people under 65 who don’t have employer coverage, opens Nov. 1. Here are the dates to mark on your calendar, what is changing for Medicare in our area, and a case study on what two very different Covered California plans would cost a hypothetical family.

Enrollment Dates at a Glance

• Medicare Annual Enrollment Period: Oct. 15 to Dec. 7, 2026. Join, switch or drop a Medicare Advantage or Part D drug plan. Changes take effect Jan. 1, 2027.¹
• Medicare Advantage Open Enrollment: Jan. 1 to Mar. 31, 2027. If you are already in a Medicare Advantage plan, switch to a different Advantage plan or return to Original Medicare.²
• Covered California (under 65, no employer plan): Nov. 1, 2026 to Jan. 31, 2027. Current enrollees can renew or switch plans starting Oct. 1. Choose a plan by Dec. 31 for coverage that starts Jan. 1. A plan chosen in January starts Feb. 1.³
• Employer plans: dates vary. Enrollment periods frequently fall in the autumn. Ask your HR department for your deadline.

Turning 65 soon? Your Initial Enrollment Period is separate from the dates above. It is a seven-month window that begins three months before the month of your 65th birthday and ends three months after it.⁴

Medicare: Many Plans Were Dropped for 2027

If you or a parent are on Medicare, read your mail carefully this month. A large number of Medicare Advantage plans have been dropped or scaled back for 2027 in San Joaquin, Contra Costa, and Alameda counties. Many of the plans leaving are PPOs, which cover out-of-network doctors, so we may see more HMO-style plans with a set network. Carriers were required to notify members by early October.

Doing nothing is not a safe default if your plan is ending! Depending on your situation, you could be moved to Original Medicare without prescription drug coverage. If your plan is affected, take these steps before Dec. 7:

• Check your doctors and hospitals against the network of any replacement plan. Do not assume a new plan works the same way as your old one.
• Check your prescriptions against the new plan’s drug list, called a formulary.
• Compare the full cost, including premiums, copays, deductibles and the maximum you could pay out of pocket in a year.

You do not have to sort through this alone. A licensed local Medicare agent can help you compare your options. Susan Lucas, a licensed insurance agent (not affiliated with WWM), is hosting Medicare educational events in our area this fall:

• Tuesday, Oct. 20, 10:00 to 11:30 a.m. ProServe Medicare Panel, Lafayette Library (Don Tatzin Hall), 3491 Mt Diablo Blvd, Lafayette
• Tuesday, Nov. 10, 9:00 to 11:00 a.m. Share Contra Costa, Pleasant Hill Senior Center, 233 Gregory Lane, Pleasant Hill⁶

Susan can be reached at 707-828-0059 or at susanplucas.com.

For a plain-English overview, download the Medicare at Retirement Cheat Sheet from Danielle McAnerney, a licensed insurance agent (not affiliated with WWM). It explains when to enroll, how Original Medicare with a Supplement compares with Medicare Advantage, Medicare costs, why to run your medication list before choosing a plan, and when HSA contributions must stop. Danielle can be reached at (831) 428-3208 or at mcanerneyinsurancesolutions.com. ⁷ 

Under 65: Choosing a Covered California Plan

Faced with a long list of plans and prices, it can be tempting to stick with the devil you know and re-enroll in your current plan. Done! But plan details change every year, and so do your needs. Premiums in our area are rising again (anyone tired of that trope yet?). Covered California reports average 2027 rate increases of 8.3% in Contra Costa County, 8.4% in Alameda County and 10.8% in San Joaquin County Region, and the extra federal subsidies that helped many households expired at the end of 2025.⁸

Look at total annual cost, not just the premium

A common mistake is choosing a plan based on the monthly premium alone. The premium is a bill you pay every month, even if you only see a doctor once a year. What you actually spend depends on several factors:

• Deductible. What you pay for covered services before your insurance begins to pay. Some services, such as preventive care, may be covered before you meet it.
• Copays and coinsurance. A copay is a flat fee for a service, such as $40 for a primary care visit. Coinsurance is a percentage of the cost you pay after meeting your deductible.
• Out-of-pocket maximum. The most you will pay in a plan year for covered, in-network care. Premiums, out-of-network care, and services the plan doesn’t cover generally don’t count toward it.
• Doctor and hospital networks. Out-of-network visits can cost much more or may not be covered at all. Confirm that your doctors and hospital are in the plan.
• Prescription coverage. Each plan has a formulary with tiers. If you take regular medications, look up each one.
• HSA eligibility. Health Savings Accounts let you save, grow, and spend money federally tax-free (still state taxable in CA and NJ) on qualified medical expenses, but they generally must be paired with a high-deductible health plan. Certain Bronze and Catastrophic Marketplace plans now count as HSA-compatible under IRS rules.⁹

Bronze vs. Gold: A Family of Four in Contra Costa County

Here is what the trade-off looks like in dollars: Imagine a married couple, both 45, with two children ages 8 and 11. They live in Contra Costa County, have no employer coverage and earn too much to qualify for premium subsidies, so they pay full price. They are comparing Kaiser Permanente’s HSA-eligible Bronze plan with its Gold plan for 2027.¹⁰

• Monthly premium for the family: Bronze about $1,988. Gold about $2,700.
• Annual premiums: Bronze about $23,853. Gold about $32,399.
• Deductible: Bronze $15,600 for the family ($7,800 per person). Gold $0.
• Out-of-pocket maximum: Bronze $15,600 for the family ($7,800 per person). Gold $19,200 for the family ($9,600 per person).
• Primary care visit: Bronze, you pay the full cost until the deductible is met. Gold, $40 copay.
• Generic prescription: Bronze, you pay the full cost until the deductible is met. Gold, $19 copay.
• HSA eligible: Bronze yes. Gold no.

What the year could cost under each plan

Total cost is the premium plus whatever you pay for care. Here are three possible years for this family:

• A quiet year. 8 office visits and 6 generic prescriptions, assuming about $150 a visit and $20 a fill before the deductible. Bronze total: $25,173. Gold total: $32,833. Bronze saves $7,660.
• One family member has a major illness or injury and reaches the out-of-pocket maximum. Bronze total: $31,653. Gold total: $41,999. Bronze saves $10,346.
• Everyone has a heavy year and the whole family reaches the out-of-pocket maximum. Bronze total: $39,453. Gold total: $51,599. Bronze saves $12,146.

Surprise! In this example, the Gold plan costs about $8,500 more in premiums, and the Bronze plan’s out-of-pocket maximum is actually lower than Gold’s, because the high-deductible design caps your spending at the deductible. That means no single person in this family can make Gold the cheaper choice. Gold only comes out ahead if the family’s out-of-pocket costs on the Bronze plan would exceed Gold’s by more than that $8,500 gap. That takes two or more people with large bills in the same year, or a household that already knows it will use a lot of care, such as ongoing specialist visits, infusions, or frequent therapy.

There is also a tax angle. The 2027 family HSA contribution limit is $9,000, up from $8,750 in 2026. A family that picks the Bronze plan could deposit the roughly $8,500 in premium savings into an HSA, deduct the contribution on your federal return (Not CA or NJ), and have that money on hand for the deductible. If the year turns out quiet, the money stays in the account and keeps growing tax-free.¹¹

What about a catastrophic plan? Covered California’s catastrophic option, which it calls “minimum coverage,” is generally limited to people under 30 and those with a hardship exemption, so this couple would likely not qualify without one. It also carries a $12,000 deductible and is not eligible for premium tax credits. The HSA-eligible Bronze plan is the closest alternative for them, but this is an interesting plan for young, healthy folks if they could pay that deductible during a catastrophy.¹²

Network matters, too. Kaiser is the least expensive option in this example, but it limits you to Kaiser doctors and facilities. If you prefer another network, the same family would pay roughly $3,400 to $4,300 a month for a Gold plan from Blue Shield or Anthem, so the premium gap between Bronze and Gold may be larger than shown here.¹³

Subsidies change the math. Federal premium tax credits generally stop at 400% of the federal poverty level, which is about $132,000 for a family of four. State help through Covered California reaches households up to 200% of the poverty level, or $66,000 for a family of four. If your income is below those lines, your premiums, and the right plan, may look very different. Run your own numbers on the Shop and Compare tool at coveredca.com.¹⁴

Changing Plans Midstream: Special Considerations

America’s employer-based health insurance system can leave people uncovered during job transitions, prompting exceptions to the open enrollment period. Under COBRA, you can continue coverage on your previous employer’s plan for a limited time, but you will pay the full monthly premium plus a 2% administrative fee because your former employer no longer contributes its share.¹⁵

For many people, a better option is buying a plan through Covered California. Losing employer-based coverage generally triggers a special enrollment period, giving you 60 days after the loss to enroll. In many cases you can also enroll during the 60 days before your coverage ends. When your new employer’s insurance begins, you can cancel the marketplace plan, or you may decide it is better than the one offered at work, especially if you qualify for a subsidy.¹⁶

If you are applying for a subsidy, estimate your total income from both jobs. If your actual income is higher than estimated, you may have received more financial assistance than you are eligible for and may have to repay the difference when you file your federal tax return.¹⁷

Along the same lines, if your new employer’s plan automatically contributes to a health savings account, make sure those contributions plus any you have already made this year won’t push you over the annual limit. For 2026, the limit is $4,400 for self-only coverage and $8,750 for family coverage. For 2027, it rises to $4,500 and $9,000. These limits apply to your total contributions across all HSA accounts, and if you are married, the family limit applies to your spouses’ combined accounts.¹⁸

A Yearly Checkup for Your Health Coverage

Open enrollment gives you a chance to make sure your health insurance still fits your needs. Take time to compare premiums, deductibles, provider networks, prescription coverage and potential out-of-pocket costs before making a decision. This can be a lot of work. But we’re here to help. Reach out if you need help evaluating how your options fit into your budget or broader financial plan.

Sources

1. Medicare Annual Enrollment Period, Oct. 15 to Dec. 7: “Medicare at Retirement” handout, Danielle McAnerney, McAnerney Insurance Solutions; ASP RCM Solutions, “Medicare Advantage Plan Exits 2027,” Aug. 15, 2026, https://asprcmsolutions.com/insights/medicare-advantage-plan-exits-2027/. Confirm on Medicare.gov.

2. Medicare Advantage Open Enrollment Period, Jan. 1 to Mar. 31: “Medicare at Retirement” handout, Danielle McAnerney, McAnerney Insurance Solutions.

3. Covered California, “Covered California Rates and Plans for 2027,” July 21, 2026 (open enrollment Nov. 1, 2026 to Jan. 31, 2027; current enrollees can renew or switch starting Oct. 1): https://www.coveredca.com/newsroom/news-releases/2026/07/21/covered-california-rates-and-plans-for-2027-california-continues-fight-for-health-insurance-affordability-and-access/. The Dec. 31 cutoff for Jan. 1 coverage matches last year’s deadline (Covered California, Dec. 22, 2025: https://www.coveredca.com/newsroom/news-releases/2025/12/22/covered-california-encourages-all-californians-to-explore-health-insurance-options-before-dec-31-deadline-to-get-coverage-for-all-of-2026/). Confirm the 2027 cutoff on coveredca.com.

4. Medicare Initial Enrollment Period: “Medicare at Retirement” handout, Danielle McAnerney, McAnerney Insurance Solutions.

5. Danielle McAnerney, McAnerney Insurance Solutions, email to Angela Wright, Oct. 6, 2026, “2027 Medicare Plan Changes in San Joaquin, Contra Costa & Alameda Counties.” Notice timing: members of continuing plans receive an Annual Notice of Change by Sept. 30, and members whose plans end receive a non-renewal notice by Oct. 2 (24/7 Wall St., Sept. 5, 2026, https://247wallst.com/personal-finance/2026/09/05/insurers-have-already-told-wall-street-which-advantage-plans-die-on-december-31-members-are-the-last-to-know-and-the-letter-isnt-due-until-october-2/).

6. Susan Lucas, Licensed Insurance Agent (CA Lic. OL70129), “Medicare Educational Events” flyer, October 2026. Event dates, times and venues are as printed on the flyer. Susan does not offer all plans in your area. Not affiliated with Wright Wealth Management. No compensation agreement. These are educational seminars.

7. “Medicare at Retirement,” Danielle McAnerney, McAnerney Insurance Solutions (CA Lic. #4410959). The handout’s cost figures are for 2026. Danielle does not offer all plans in your area. Not affiliated with Wright Mouth Management. No compensation agreement. Her document is for educational purposes only.

8. Covered California, “Covered California Rates and Plans for 2027,” July 21, 2026: https://www.coveredca.com/newsroom/news-releases/2026/07/21/covered-california-rates-and-plans-for-2027-california-continues-fight-for-health-insurance-affordability-and-access/. Regional averages: Contra Costa is Region 5 (8.3%), Alameda is Region 6 (8.4%) and San Joaquin is in Region 10 (10.8%), which also includes Stanislaus, Merced, Mariposa and Tulare counties (Contra Costa News, July 22, 2026, https://contracosta.news/2026/07/22/covered-california-rates-to-rise-8-3-in-contra-costa-county-for-2027/). The release also states that the enhanced federal tax credits expired at the end of 2025.

9. IRS, “Treasury, IRS provide guidance on new tax benefits for health savings account participants under the One Big Beautiful Bill”: https://www.irs.gov/newsroom/treasury-irs-provide-guidance-on-new-tax-benefits-for-health-savings-account-participants-under-the-one-big-beautiful-bill

10. Premiums are preliminary 2027 Kaiser Permanente rates for Contra Costa County, which Covered California lists at $575 (Bronze HDHP) and $781 (Gold) a month for a 40-year-old. I scaled them to this family using the standard age-rating curve. Kaiser rates in Alameda County are about 1% lower. Cost-sharing reflects Covered California’s proposed 2027 standard plan designs. Your own quote will vary with your ages, county and plan. Sources: Covered California, 2027 Sample Health Plan Rates by County (data as of Aug. 23, 2026, published Oct. 1, 2026; preliminary and under Department of Managed Health Care review): https://hbex.coveredca.com/toolkit/downloads/2027_Health_Plan_Rates_by_County.pdf. Cost-sharing: Covered California PY 2027 Patient-Centered Benefit Plan Designs (June 18, 2026 board proposal): https://board.coveredca.com/meetings/2026/June%2018,%202026/2026.06.18_PY_2027_Patient_Centered_Benefit_Plan_Designs_Updated_06.2026.pdf, and Cover Health CA, 2027 plan comparison: https://www.coverhealthca.com/learn/choosing-a-plan/2027. Calculation: each family premium is the 40-year-old rate times 3.457, the sum of two adults at age 45 (1.444 / 1.278 each) and two children under 15 (0.765 / 1.278 each) on the federal standard age curve. Bronze HDHP: $575 x 3.457 = $1,988 a month. Gold: $781 x 3.457 = $2,700 a month. Alameda County Kaiser rates are $568 and $772 for the same plans.

11. IRS Rev. Proc. 2026-24 (2027 HSA limits: $4,500 self-only, $9,000 family), as reported by the International Foundation of Employee Benefit Plans, June 1, 2026: https://www.ifebp.org/detail-pages/news/2026/06/01/irs-releases-2027-hsa–hdhp–and-hra-inflation-adjusted-amounts. 2026 limits: IRS Notice 2026-5, https://www.irs.gov/pub/irs-drop/n-26-05.pdf.

12. Cover Health CA, “Choosing a Covered California plan for 2027” (minimum coverage eligibility, $12,000 deductible, no premium tax credits): https://www.coverhealthca.com/learn/choosing-a-plan/2027. Secondary source. Confirm on coveredca.com.

13. Covered California, 2027 Sample Health Plan Rates by County, Contra Costa (Region 5), age 40, Gold: Blue Shield HMO $996, Blue Shield PPO $1,182, Anthem EPO $1,257 a month. Each multiplied by the 3.457 family factor: $3,443, $4,086 and $4,345. https://hbex.coveredca.com/toolkit/downloads/2027_Health_Plan_Rates_by_County.pdf

14. Covered California, July 21, 2026 release: 200% of the federal poverty level is $66,000 for a family of four, so 400% is $132,000; state subsidy funding reaches households up to 200%: https://www.coveredca.com/newsroom/news-releases/2026/07/21/covered-california-rates-and-plans-for-2027-california-continues-fight-for-health-insurance-affordability-and-access/

15. COBRA premium cap of 102% of the plan cost: 29 U.S.C. § 1162(3).

16. HealthCare.gov, “Special enrollment period”: https://www.healthcare.gov/glossary/special-enrollment-period/. Confirm the Covered California rules at coveredca.com.

17. IRS, Form 8962 and instructions (Premium Tax Credit reconciliation): https://www.irs.gov/forms-pubs/about-form-8962

18. 2026 limits: IRS Notice 2026-5, https://www.irs.gov/pub/irs-drop/n-26-05.pdf. 2027 limits: IRS Rev. Proc. 2026-24, as reported at https://www.ifebp.org/detail-pages/news/2026/06/01/irs-releases-2027-hsa–hdhp–and-hra-inflation-adjusted-amounts. Spouses and family coverage: IRS Publication 969, https://www.irs.gov/publications/p969.

Information is provided for informational purposes only and should not be relied upon in any manner as professional advice, or an endorsement of any practices, products, or services. There can be no guarantees or assurances that the views expressed here will be applicable for any particular facts or circumstances and should not be relied upon in any manner. You should consult your own advisers as to legal, business, tax, and other related matters concerning any investment.The commentary in this post (including any related blog, podcasts, videos, and social media) reflects the personal opinions, viewpoints, and analyses of Angela Wright, an Investment Adviser Representative of Gemmer Asset Management LLC (“GAM”) and should not be regarded as the views of GAM, or a description of advisory services provided by GAM or performance returns of any GAM client.  References to securities or market-related performance data are for illustrative purposes only and do not constitute an investment recommendation or offer to provide investment advisory services. Charts and graphs provided within are for informational purposes solely and should not be relied upon when making any investment decision. Past performance is not indicative of future results. The content speaks only as of the date indicated. Any projections, estimates, forecasts, targets, prospects, and/or opinions expressed in these materials are subject to change without notice and may differ or be contrary to opinions expressed by others. The information presented herein may contain links to third party websites with which we have no affiliation. A link to any third-party website does not mean that we endorse it, or the quality or accuracy of the information presented on it.