Enrollment Window Checker
Enter your birthday and get your exact Initial Enrollment Period dates, your Medigap open enrollment window, and the deadlines that carry lifetime penalties.
Check my datesFree tool
Six questions. It won't name a plan — no honest tool can — but it will tell you which side of the fork your situation points to, and what would change the answer.
Where this points
This runs entirely in your browser. Nothing you select is sent anywhere or stored.
It is a directional read on plan structure, not a recommendation of any specific plan, carrier or product. A real recommendation requires checking your named doctors against each network and pricing your named medications against each formulary — which is what a conversation is for.
There is no black box here, so here is the whole logic. Four of the six answers push toward one structure or the other:
If you are new to Medicare, your Medigap open enrollment period means a Supplement is available to you without health questions. That window runs six months from the month you turn 65 and are enrolled in Part B, and it does not come back. If the result leans toward a Supplement and you are in that window, the timing matters as much as the reasoning.
If you have been on Medicare a while, moving to a Supplement generally means answering health questions in Arizona. That does not make it impossible — it makes it something to check before you plan around it.
Other tools
Enter your birthday and get your exact Initial Enrollment Period dates, your Medigap open enrollment window, and the deadlines that carry lifetime penalties.
Check my datesCompare what a year on a Medicare Advantage plan versus a Supplement plus Part D would realistically cost you — premiums, deductibles and expected visits included.
Estimate my yearHigher income means a surcharge on Part B and Part D. See which bracket your tax return puts you in before the letter arrives.
Check my bracketNext step
One conversation, no cost, no obligation. Bring your prescription list and your doctors — that is all it takes to do real work. You’ll speak to Brian Penner directly.