By Grant MercerLast updated Oct. 7, 2026Image: cottonbro studio/Pexels
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Medicare’s cap on out-of-pocket prescription costs is $2,400 in 20271, and the Part B premium alone now takes more than $200 a month out of most Social Security checks.
Between premiums, drug costs, the bills Medicare doesn’t cover and the taxes on what you withdraw, health care is one of the biggest line items in retirement. Most people overpay on at least a few of them without realizing it.
Here are the moves worth making, including a few options from our partners:
Medicare Plans: Don't let your plan auto-renew without checking it
If you do nothing during Open Enrollment, which runs every fall from Oct. 15 to Dec. 7, your plan simply renews. That sounds easy, but premiums, covered drugs and doctor networks change every January, and the plan that fit this year can cost hundreds more next year.
Every plan mails an Annual Notice of Change each fall. That’s your starting point. RetireShield’s Open Enrollment Decision Kit takes it from there, with a cost calculator that compares plans on premiums, drugs and doctors side by side, a call script for checking your providers, and the full Open Enrollment calendar.
Get the 2027 Open Enrollment Decision Kit
Out-of-pocket drug costs in Part D are capped at $2,100 in 2026 and $2,400 in 2027. Once you hit the cap, covered drugs cost nothing more for the rest of the year.
Prescription Costs: Have a licensed agent run your drugs against every plan
The plan with the lowest premium is often not the cheapest once your prescriptions are counted, and drug lists change every January.
GoHealth has licensed agents who compare Medicare Advantage and Part D plans from multiple insurance companies, using your exact prescriptions, pharmacy and doctors. The service costs you nothing, because the insurers pay them.
Have your current plan card and a list of your medications and doses ready before you call.
Compare Medicare plans with GoHealth
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
Have your Medicare card, every prescription with its dose, and your pharmacy’s name ready before you compare plans. The drug-cost estimate is only as good as that list.
Medicare Advice: Get a plan review from an advisor who compares across insurers
Most people who call the number on a TV ad end up talking to an agent who can only sell a few companies’ plans. That’s not the same as a full comparison.
Chapter has licensed advisors who compare Medicare Advantage, Medigap and Part D options across many insurers, and help you decide whether to stay on Original Medicare or switch.
Bring a list of your doctors and prescriptions to the call so they can check coverage line by line.
Get a Medicare plan review from Chapter
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
Part B Premiums: Let your state pay your $200-plus premium
The standard Part B premium is more than $200 a month3, taken out of most Social Security checks before they’re deposited. A Medicare Savings Program, run by your state, can pay it for you, and at the most generous level also covers deductibles and copays.
Many states set their limits higher than the federal minimum, so people who assume they earn too much are often wrong.
RetireShield’s Medicare Cost & Coverage Protection Kit includes a cost-help pack for every state, the Part D out-of-pocket cap rules and the prior-authorization appeal steps.
Get the Medicare Cost & Coverage Protection Kit
Part D: Compare every drug plan in your ZIP code side by side
Part D plans change their drug lists, pharmacies and prices every January, and the cheapest plan for you this year may be one of the most expensive next year.
eHealth lets you enter your prescriptions and pharmacy and see estimated yearly costs across the plans it offers in your area, then enroll online or with a licensed agent.
Run your actual drug list, not just the premium. The plan with the lowest premium is often not the cheapest once your prescriptions are counted.
Compare Medicare drug plans with eHealth
We do not offer every plan available in your area. Any information we provide is limited to those plans we do offer in your area. Please contact Medicare.gov or 1-800-MEDICARE to get information on all of your options.
Not Having Enough in Retirement: Get your income plan checked
Withdrawals, Roth conversions and tax brackets all affect what Medicare costs you. If you have $250,000 or more saved, the order you draw from accounts and when you do it can change how long your money lasts by years.
Datalign Advisory asks a few questions and matches you with financial advisors in your area. Ask any advisor exactly how they’re paid before you commit to anything.
Get matched with a financial advisor near you
Lifetime Income: Lock in a monthly check on top of Social Security
Worried about outliving your savings? An income annuity turns a lump sum into monthly payments, for a set number of years or for life. Payout rates move with interest rates, so what a given amount buys changes from year to year.
Annuity.org explains how the different types work and can connect you with a licensed professional to compare quotes. Annuities can be hard to undo and some carry surrender charges, so compare several and read the contract.
Learn how income annuities work at Annuity.org
Market Volatility: Before you move any retirement money, learn how a gold IRA works
A move like the ones on this list is easier to judge with the rules in front of you. Birch Gold Group's free Insider's Guide to Gold IRAs walks through how a gold IRA is opened and funded, and a precious metals specialist answers questions before you decide anything.
Get the free Insider's Guide to Gold IRAs from Birch Gold Group →
Weak Dollar: Hold part of your savings in something the Fed can't print
A falling dollar quietly shrinks what a fixed income buys. Some retirees hold a share of their savings in physical gold and silver, which have historically held value over long stretches when the dollar weakened.
Lear Capital has sold gold and silver to retirement savers for decades and can set up a precious metals IRA or ship metals to you directly. Prices fall as well as rise and dealers charge a markup over spot, so ask for the total cost and the buyback price in writing before you buy.
Learn about precious metals IRAs from Lear Capital
Investments carry risk. Past performance is not a guarantee of future results. We may be compensated if you sign up through this link.
Required Withdrawals: Time your RMD so it doesn't raise your Medicare premiums
If you’re 73 or older, you must take a required minimum distribution from traditional IRAs and most workplace plans by December 31 each year. Miss it and the IRS charges an excise tax on the shortfall.
How much you take, from which account and when can also push you into a higher tax bracket or trigger Medicare surcharges two years later.
WiserAdvisor matches you with financial advisors in your area who can map out withdrawals year by year. It costs nothing to get matched; ask any advisor exactly how they’re paid.
Get matched with a financial advisor through WiserAdvisor
Medicare Surcharges: Appeal IRMAA if your income dropped
Medicare’s income surcharges, called IRMAA, are based on your tax return from two years ago. If your income has since dropped because you retired, lost a spouse or got divorced, you can ask Social Security to use the lower figure with Form SSA-44.
RetireShield’s Retirement Tax & Withdrawal Planner walks through the appeal, plus calculators for IRMAA tiers, RMDs and Roth conversions, and the order to draw from your accounts.
Get the Retirement Tax & Withdrawal Planner
Burial Insurance: Lock in a rate before your next birthday
Final expense policies are priced by age, so the rate you’re offered goes up every year you wait. A small policy, often $10,000 to $25,000, is meant to cover the funeral and the last bills so your family doesn’t have to.
Ethos sells life insurance online, including whole life coverage meant for final expenses, for people up to age 85. Many applicants answer a few health questions and never need a medical exam.
Compare the monthly price and ask whether the full benefit is paid from day one or only after a waiting period.
Check final expense rates with Ethos
Insurance Renewals: Shop before the renewal notice hits
Renewal notices land 30 to 60 days ahead, and that’s the window to shop. Insurers price renewals for customers they expect to stay, which is why loyal customers often pay the most.
SmartFinancial gathers quotes from several insurers at once. Compare the same limits and deductibles, and ask about low-mileage and mature-driver discounts.
Here’s how it works:
- Enter your ZIP code and a few details about your car or home.
- See quotes from multiple insurers side by side.
- Switch only if the same coverage costs less, or keep the policy you have.
Compare home and auto insurance quotes
High-Interest Debt: Look at your options for a 22% card balance
Credit cards that carry a balance charged an average of 22.15% interest4 in May 2026, according to the Federal Reserve. On a $10,000 balance that’s about $185 a month in interest alone.
CuraDebt connects consumers with independent debt relief providers. If you have $15,000 or more in unsecured debt, such as credit cards, medical bills or personal loans, a free evaluation shows the options that may be available before you decide anything. Debt amount is one factor and does not determine qualification.
Here's how it works:
- Answer a few questions about what you owe.
- A specialist reviews your balances and explains the options that may be available.
- If a program fits, you see the estimated cost and timeline before you decide.
Advertisement. CuraDebt connects consumers with independent debt relief providers. Results not guaranteed. Debt amount is only one factor and does not determine qualification. Not all consumers qualify, and not all debts are eligible. Creditors are not required to agree to settlements. Debt relief services may adversely affect your creditworthiness. Typical program duration is 24 to 48 months. This site may be compensated for referrals to CuraDebt.
Medicare Scam Calls: Get your number off the lists
Scam calls about "new Medicare cards," plan refunds and free medical equipment spike every fall during Open Enrollment. Medicare does not call to ask for your Medicare number.
Scammers get your name and number from data brokers and people-search sites. Incogni sends removal requests to those sites on your behalf and keeps re-sending them, which can mean fewer scam calls, texts and emails.
See how Incogni removes your info from data broker lists
Property Taxes: File for your senior exemption before the deadline
Many counties set filing deadlines for senior exemptions and assessment freezes early in the year, and very few apply them automatically. Miss the window and you usually wait another year.
RetireShield’s Property Tax & Home-Cost Relief Kit covers all five kinds of property tax relief, including circuit-breaker credits that refund part of the rent for older renters, with a renewal calendar so you don’t miss the next deadline.
Get the Senior Property Tax & Home-Cost Relief Kit
Online Shopping: Get cash back on things you already buy
Prescriptions, vitamins, household supplies and gifts add up. If you’re buying them online anyway, there’s no reason to leave cash back on the table.
Rakuten pays you a percentage back when you shop at thousands of partner stores through its site or browser extension,. The money builds up and gets paid out by check or PayPal on a regular schedule.
It doesn’t change what you pay at checkout, so it works best on purchases you’d make anyway.
Join Rakuten and start earning cash back
You don’t have to do all 20. Start with the ones that touch your biggest bills, then work down the list.
For Medicare and money moves like these in your inbox each weekday, sign up for the free Retirement Money Brief.
