Why an Annual Medicare Plan Review Can Save You Money
Ryan Olson | Aug 03 2026 14:00
Medicare plans can change their premiums, prescription drug formularies, provider networks, and benefits every year. Staying in the same plan out of habit is one of the most common ways Medicare beneficiaries overpay or discover too late that a medication, doctor, or benefit no longer works the way it did before. An annual review gives you a practical chance to make sure your coverage still fits your health needs and budget.
At Red Sky Insurance Advisors, Ryan Olson believes Medicare coverage deserves more than a one-time decision. That is why Ryan reviews every client’s plan before the Annual Election Period (AEP) without waiting to be asked. It is a proactive, no-cost way to help clients throughout Wisconsin make confident decisions before next year’s coverage begins.
Why Medicare Coverage Needs a Fresh Look Every Year
A plan that was an excellent fit last year may not be the best value next year. Medicare Advantage and Part D prescription drug plans renew their contracts annually and may update their monthly premiums, deductibles, copays, coinsurance, pharmacy networks, provider networks, and covered-drug rules.
Even a small change can have a meaningful effect. A preferred pharmacy may no longer offer the best pricing. A prescription may move to a higher formulary tier. A specialist you see regularly may leave a network. Dental, vision, hearing, over-the-counter, transportation, or other extra benefits can also change from one plan year to the next.
For people with Original Medicare and a Medicare Supplement policy, the conversation can look different. Your Medigap coverage may remain stable while your separate drug plan changes substantially. Reviewing the whole picture—not just one card in your wallet—helps prevent a costly gap in coverage.
Start With Your Annual Notice of Change Letter
Your plan sends an Annual Notice of Change, often called an ANOC, each fall. This letter explains changes that will take effect on January 1. It may not be exciting reading, but it is one of the most important Medicare documents you receive all year.
When you open the letter, compare the current year with the coming year and focus on these areas:
- Monthly premium and deductible: Look for changes in what you pay before and after using care.
- Copays and coinsurance: Pay close attention to primary care, specialists, hospital stays, outpatient surgery, urgent care, and diagnostic testing.
- Prescription coverage: Check each medication’s formulary tier, restrictions, prior authorization rules, quantity limits, and step therapy requirements.
- Pharmacies and providers: Confirm that your preferred pharmacy and the doctors, hospitals, and specialists you value are still available under the plan’s rules.
- Extra benefits: Review the allowances and limitations for dental, vision, hearing, fitness, transportation, and over-the-counter items.
The ANOC tells you what is changing in your current plan. It does not automatically tell you whether another option may serve you better. That comparison is where an experienced independent Medicare insurance advisor in Wisconsin can be especially helpful.
What Should Trigger a Medicare Plan Review?
Every Medicare beneficiary should review coverage annually, but certain changes make a careful review especially important. If you had a health change, a new diagnosis, a hospitalization, or more frequent specialist care, your current plan may no longer align with the care you need.
Medication changes are another major trigger. A new prescription, a dose change, or a medication that becomes more expensive can alter your total yearly costs quickly. This is particularly important for people enrolled in Part D Plans, because drug formularies and pharmacy pricing can vary widely.
You should also review your plan if you moved, your preferred doctor changed practices, a hospital system changed its network participation, or you were surprised by out-of-pocket costs during the year. A change in your budget matters too. The plan with the lowest premium is not always the plan with the lowest total cost once prescriptions, copays, and expected care are included.
When Switching Plans Makes Financial Sense
Switching plans may make financial sense when the expected savings or improved coverage outweighs the disruption of changing. For example, a different plan may place your medications on lower tiers, include your preferred pharmacy at a better cost-sharing level, offer a stronger provider network for your needs, or reduce expected copays for services you use often.
It can also make sense to switch when your current plan eliminates a benefit you rely on or raises its maximum out-of-pocket exposure beyond what feels comfortable. The goal is not to chase every small benefit or choose based on a television commercial. The goal is to compare the full annual cost and practical value of coverage based on your
doctors, prescriptions, travel habits, health priorities, and financial comfort level.
There are important tradeoffs. Moving from Medicare Advantage back to Original Medicare may create a need for a separate Part D plan and may raise questions about Medicare Supplement eligibility. In Wisconsin, Medicare Supplement options have their own structure and rules, so a plan change should be reviewed carefully before you enroll. Ryan Olson helps clients understand those choices rather than making a rushed decision based on one number.
Why Work With an Independent Medicare Broker?
Red Sky Insurance Advisors is an independent brokerage. Ryan Olson represents multiple carriers and reviews options based on what fits each client’s needs—not on carrier incentives. That matters when comparing Medicare Advantage plans, Medicare Supplement coverage, and prescription drug plans in Wisconsin.
Ryan’s approach is simple: before AEP, he reviews each client’s plan without being asked. He checks for changes, asks about medications and providers, and identifies whether staying put or exploring alternatives makes the most sense. Clients do not need to know every rule or spend hours sorting through plan materials alone.
If you are looking for a Medicare broker in Fitchburg, Madison, or elsewhere in Wisconsin, that annual check-in can offer valuable peace of mind. You can learn more about Red Sky’s Annual Plan Review
process and what a proactive review includes.
Timing Matters: Review Before AEP Ends
Medicare’s Annual Election Period runs from October 15 through December 7 each year. Changes made during that window generally take effect on January 1. Waiting until the final days can make an already complicated decision feel more stressful, especially if you need to verify doctors, prescriptions, pharmacies, and plan details.
A better approach is to review your ANOC as soon as it arrives, gather an up-to-date medication list, and schedule time to compare your choices early. If your current plan still fits, you can keep it with confidence. If it does not, you will have time to evaluate alternatives thoughtfully.
FAQ
Do I have to change Medicare plans every year?
No. If your plan is still available and continues to meet your needs, staying enrolled may be the right choice. The important step is reviewing it rather than assuming it has not changed.
Will an annual review cost me anything?
No. Red Sky Insurance Advisors offers free consultations and annual reviews. Ryan Olson can help you evaluate your options without pressure or obligation.
Should I review my plan if my health has not changed?
Yes. Plan premiums, formularies, pharmacies, provider networks, and benefits can change even when your health does not. A review can confirm whether your coverage remains a good value.
What should I bring to a Medicare plan review?
Bring your current plan information, your ANOC letter, a current list of prescriptions and dosages, your preferred pharmacies, and the names of doctors or specialists you want to keep seeing.
Can Ryan Olson help if I live outside Wisconsin?
Ryan serves Medicare clients in Wisconsin and is also licensed in Minnesota, Illinois, Texas, Arizona, and Washington. Availability depends on your state and the plans offered where you live.
Request Your Free Annual Medicare Review
Do not let another year of automatic renewal decide what you pay for Medicare coverage. Request a free annual review with Ryan Olson at Red Sky Insurance Advisors to see whether your current plan is still working as hard for you as it should. A short conversation now can help you enter the new year with clearer coverage, fewer surprises, and greater confidence.
About the Author
Ryan Olson

Ryan Olson is an independent Medicare and health insurance advisor based in Fitchburg, Wisconsin. Since 2017, he's helped individuals across Wisconsin and beyond navigate their Medicare options — comparing plans across 13+ carriers to find coverage that actually fits each client's health needs and budget. As an independent broker, Ryan works for his clients, not the insurance companies, and his consultations are always free. When he's not helping someone make sense of Medicare, you'll likely find him planning his next adventure or logging miles on the train. Have a question about your coverage? Reach out at ryan@askredsky.com or call the office at (608) 608-7460.
