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The do’s and don’ts of preparing for Open Enrollment

Open Enrollment — and Medicare’s Annual Election Period — can be overwhelming. With so many options to choose from in a short amount of time, it can be pretty confusing and hard to keep up with. But help is on the wayWe’ve got some do’s and don’ts to share, so you can take on this annual task with confidence.  


First things first: take a deep breathThen grab pen and some paper. With a little preparation, you’ll be on your way to signing up in no time, without any added stress. But before we dive into a to-do list, let’s talk about what we’re preparing for — and how much time we have to do it. 


What is Open Enrollment? 

Open Enrollment is the annual period of time when people can enroll in or change their health insurance for the next calendar year. If you miss Open Enrollment or would like to change your plan outside of this time frame, you have to wait for a qualifying event, like getting married, having a baby, or losing health coverage. For more information on qualifying eventshead here 

Open Enrollment typically runs from November 1 to December 15 every year, but this also depends on your state. (For example: New York’s Open Enrollment period extends until January 31.)


What is the Medicare Annual Election Period? 

There are actually two opportunities for those that qualify for Medicare to enroll in or change their coverage.  


The first is Medicare’s Annual Election Period, and your selections during this time will go into effect on January 1. The second is Medicare Advantage’s Open Enrollment Period. 

If you qualify for Medicare and are looking into your options for the next year, here’s what you can do:  



Annual Election Period 

Open Enrollment  

October 15 – December 7 

  • Change from Original Medicare (Parts A and B) to Medicare Advantage (Part C). 

  • Change from Medicare Advantage to Original Medicare. 

  • Switch Medicare Advantage Plans. 

  • Switch from Medicare Part D (prescription drug) Plans. 

  • Switch from a Medicare Advantage Plan that does not offer drug coverage to a Medicare Advantage Plan that does. 

  • Enroll in or cancel a Medicare Part D Plan. 


January 1 – March 31 


  • Switch Medicare Advantage plans. 

  • Return to Original Medicare. 

  • Enroll in a Part D Plan. 


Here are the do’s and don’ts of picking a healthcare plan. 

Now that you know when and what you need to sign up for, let’s talk about the do’s and don’ts of how to prepare.  


Do: Gather your personal information before you apply.  

When you enroll in or renew your coverage, you’ll be asked to provide information on any dependents, your household income, and key details like your Social Security number and address. If you’re currently enrolled in coverage, you should have your policy handy, too. (This makes it easier to compare it against new plans in case you’d like to switch.) 


Don’t: Just assume your current health plan is the best option. 

Plans change annually — and if you’re not careful, you can re-enroll in a plan with higher rates, different coverage options, and a new network of doctors. If you’re happy with your current plan, that’s great! But before you agree to another year of coverage, make sure you read the fine print — just in case.  


Do: Make a list of must-haves.   

Do you have a specialist you really like? Would you prefer a plan with easily accessible telemedicine options? By defining a list of must-haves for insurance, it will be that much easier to sift through plans and create your “short list” of ones to choose from. Here are some considerations to get you started:  

  • A big network of doctors  

  • Low monthly costs vs. a low deductible  

  • Prescription drug coverage options 

  • An HSA-eligible plan 

  • Out-of-network coverage options  

  • Your maximum out-of-pocket cost 

Don’t: Wait.  

Your enrollment deadline and signup method (over the phone or online) depend on your primary home state. You’ll want to make sure you’re giving yourself enough time to find a plan and think it over — because after the deadline, you’ll have to wait a whole year (or for a qualifying event) to enroll.  

When is your state's deadline?


State Open Enrollment Dates
CALIFORNIA October 15th - January 31st
ALABAMA November 1st - December 15th
ALASKA November 1st - December 15th
ARIZONA November 1st - December 15th
ARKANSAS November 1st - December 15th
COLORADO November 1st - December 15th
DELAWARE November 1st - December 15th
DISTRICT OF COLUMBIA November 1st - December 15th
FLORIDA November 1st - December 15th
GEORGIA November 1st - December 15th
HAWAII November 1st - December 15th
IDAHO November 1st - December 15th
ILLINOIS November 1st - December 15th
INDIANA November 1st - December 15th
IOWA November 1st - December 15th
KANSAS November 1st - December 15th
KENTUCKY November 1st - December 15th
LOUISIANA November 1st - December 15th
MAINE November 1st - December 15th
MARYLAND November 1st - December 15th
MICHIGAN November 1st - December 15th
MISSISSIPPI November 1st - December 15th
MISSOURI November 1st - December 15th
MONTANA November 1st - December 15th
NEBRASKA November 1st - December 15th
NEVADA November 1st - December 15th
NEW HAMPSHIRE November 1st - December 15th
NEW JERSEY November 1st - December 15th
NEW MEXICO November 1st - December 15th
NORTH CAROLINA November 1st - December 15th
NORTH DAKOTA November 1st - December 15th
OHIO November 1st - December 15th
OKLAHOMA November 1st - December 15th
OREGON November 1st - December 15th
PENNSYLVANIA November 1st - December 15th
SOUTH CAROLINA November 1st - December 15th
SOUTH DAKOTA November 1st - December 15th
TENNESSEE November 1st - December 15th
TEXAS November 1st - December 15th
UTAH November 1st - December 15th
VIRGINIA November 1st - December 15th
VERMONT November 1st - December 15th
WASHINGTON November 1st - December 15th
WEST VIRGINIA November 1st - December 15th
WISCONSIN November 1st - December 15th
WYOMING November 1st - December 15th
MINNESOTA November 1st - December 23rd
RHODE ISLAND November 1st - December 31st
CONNECTICUT November 1st - January 15th
MASSACHUSETTS November 1st - January 15th
NEW YORK November 1st - January 15th


Do: Define your budget.  

Like your coverage must-haves, creating a budget is just as important. Would you prefer a plan that has a higher monthly cost — but a low deductible? And how high can that monthly cost comfortably be? Determining this now can save you a lot of headache later, because an unexpected health bill can have a huge financial impact 


Don’t: Be afraid to ask for help.  

Signing up for a healthcare (or Medicare!) plan is one of the most important things you can do to make you and your family feel safer, have more access, and keep costs down. That’s why Kasasa Care has partnered with KindHealth to create a digital platform to find plans, compare prices, and get help — with ease. You don’t have to do this alone, and Kind Advisors are standing by to answer your questions, explore your Medicare options (if you qualify), and help you navigate this important time like a pro. Plus, if you have a question about a medical bill or don’t fully understand your benefits, they’re always just a phone call away — long after you’ve enrolled in coverage. 


As Open Enrollment approaches, it’s easy to feel anxious. Making your healthcare or Medicare choice for the next calendar year is a huge decision, but we hope these tips made you feel more at ease — and more equipped to get enrolled. Be well!  

Tags: Health, Health Insurance, Care, Medicare

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