Retiring at year end

I retired at 66+, some months after my FRA. I picked up Medicare so that it took effect immediately upon my retirement.

At your age you should get a big boost in your SS benefit due to delayed retirement credits.

Good luck!

@KarenD738143 

Have you checked the Medicare website?

Welcome to Medicare | Medicare

Have you checked information about a Medicare advantage plan?

Have you created an account with Social Security?

The United States Social Security Administration | SSA

When to apply for SS depends on what month you want your first payment.  SS is paid in arrears so a December start will provide the first payment in January.  You can apply for SS the 4th month before your start month.  For a December start, you could've applied starting Aug 1.  A December start will have the 2025 COLA but not your 2024 earned Delayed Retirement Credit (DRC) of 8%.  The 8% for 2024 will appear in the January benefit paid in February because DRC is only applied starting in January of each year.

Because you are past your Full Retirement Age (FRA), SSA will ask you if you'd like to back date your application up to 6 months and receive a lump sum payment.  You get a large payment but you also lose the 4% DRC earned for the last 6 months of 2024.  It can be a large payment so think about it carefully before making a decision.  The difference in SS payments takes about 10 years for the total received to be equal.  Lump sum vs 10 years of higher payments.

Medicare can be signed up for 3 months before the month you stop working and up to 3 months after you stop working without penalty, so September thru March for a December start month.  That's a 7 month window.  You may need a letter from your HR stating you have been covered by creditable health insurance since you were 65 to avoid any penalty for not having signed up at 65.  If you have an option to keep your company insurance in retirement (NOT COBRA), you might want to consider keeping it as a supplemental plan to Medicare.  I'd have Medicare start the month after your current insurance expires because in most cases, if there is any overlap, Medicare becomes primary and your company plan becomes secondary.  Check with HR.  You don't want to get hit with Medicare deductibles for just one month because it became the primary insurance if you already paid your employer plan deductibles for the year.