Frequently Asked Questions

It depends on your doctors, medications, budget, and tolerance for out-of-pocket risk. That’s why working with a broker like SkyWell Benefits can be so valuable—we help you compare your options, avoid costly mistakes, and guide you through the process at no additional cost to you. 

A broker helps you compare multiple companies, explain the differences, and find the plan that actually fits your doctors, prescriptions, and budget—without you having to navigate everything alone. 

No. You do not pay more to use a broker. The premiums are the same whether you enroll on your own, through a carrier, or through a licensed agent.

You can apply for Medicare online at SSA.gov, in person at your local Social Security office, or by calling the Social Security Administration directly. If you are already receiving Social Security benefits or have been classified as disabled for more than two years, you may be automatically enrolled. 

 Your Initial Enrollment Period starts 3 months before you turn 65 and lasts 7 months total. If you don't enroll, you'll have to wait until the General Election Period (Jan 1st thru March 31st) of the following year.

 Not always. If you have credible employer coverage, you can delay without penalty. However, if you don't have creditable coverage, then you could be subject to lifetime penalties for both part B and part D of Medicare.

Original Medicare does not cover routine dental or vision services. However, many Medicare Advantage plans include these benefits. If you have Original Medicare, you may want to consider purchasing a standalone dental and/or vision plan to meet your needs. These plans are available year-round, and many individuals choose to enroll in them for additional coverage.

Open Enrollment typically runs from November 1 through January 15 each year. Outside of this window, you may qualify for a Special Enrollment Period (SEP) if you experience a qualifying life event—such as moving, losing coverage, gaining U.S. citizenship, turning 26 and aging off a parent’s plan, or getting married or divorced. Most qualifying events provide a 60-day window from the date of the event to enroll in coverage.

 It’s important to update your income whenever it changes. Doing so helps ensure your subsidy is accurate and can prevent unexpected tax bills or adjustments at the end of the year. Please reach out to me and I can help you adjust it so there are no complications with the application. 

 Typically at least 2 employees (varies slightly by state and carrier). 

 A minimum percentage of employees must enroll, often ~50%, unless it’s open enrollment season (typically Nov/Dec depending on company).  

 Any time of year—as long as eligibility and participation requirements are met.