What Is Part D, and Do You Really Need It?

Welcome to Day 4 of the "New to Medicare" Bootcamp!

If you’ve been following along, you know this Bootcamp is all about learning Medicare in the right order, to keep it streamlined without overwhelm (without spending hours Googling things you’re not even sure apply to you).

And you're joining us today for Day 4 of the Medicare Bootcamp but missed Day 3, don't stress, you can catch up anytime! We talked all about Medigap vs. Medicare Advantage (and it's a good one).

Head over here to read Day 3.

Now, let’s talk about something that trips everyone up…

When (and How) to Sign Up

You won’t sign up for Part D at the same time you enroll in Part A and B. Instead, you’ll do it once you have your Medicare number but before your coverage starts.  The same applies coming off a work plan and adding Part B later.  You sign up in advance for Part D coverage to begin the day after your employer plan ends.

Now here’s the kicker:
If you’re not getting drug coverage through your employer, retiree plan, or the VA, and you skip signing up when you’re first eligible… you could get hit with a lifetime penalty.

Yep, lifetime.

Even if you don’t take any prescriptions right now, it’s still a good idea to enroll in the cheapest plan available in your area (some are as low as $0/month!) - just so you don’t end up paying more later.

Common Mistakes (That Are Totally Avoidable)

Here are two big ones I see all the time:



1. Picking the same company for your Medigap and drug plan just because it feels simpler. (Don’t do this without checking how your prescriptions are actually covered!)
2. Never reviewing your drug plan again after the first year. Plans change every year—and you could be overpaying big time if you don’t double-check things during open enrollment each fall.

How to Find the Right Plan for You

There’s no one-size-fits-all when it comes to Part D.

The “best” plan for someone else might be a terrible fit for your prescriptions.

Here’s what I recommend:

• Start with a full list of your medications (correct name for the brand or generic, dosage, how often you take them)
• Use the Plan Finder tool on Medicare.gov to compare plans based on your actual drugs and your favorite pharmacy
• Or if you’re working with me, I can run it through my agent-only software that saves a ton of time and finds your top 3 plans instantly

📝 Pro Tip: Even if you do your own search, you can still have me help with your plan enrollment as a free add-on service when I handle your Medigap or Advantage Plan, so you’ve got someone in your corner if issues pop up later.

Bonus Tips for Getting the Best Deal

• Check GoodRx.com and CostPlusDrugs.com to compare cash prices for your meds (sometimes it’s cheaper to pay outside your plan!)
• If one of your meds is outrageously priced in every Part D plan, take it out of your drug list and rerun the search (especially if you plan to get it covered a different way, such as through a Canadian Pharmacy). You might uncover better plan options.
• Review your plan every fall. Drug prices, copays, and coverage can all change year to year.

If You’re Still Working…

You might not need a Part D plan right now if your employer coverage is considered “creditable.” That just means it’s as good or better than Medicare’s drug coverage. You can check with your HR department to confirm.

But once that coverage ends, you’ve got a short 63 day window to enroll in a Part D plan without a penalty.

don’t miss that deadline!

You’ve Got Options and Support

Choosing the right drug plan is one of the most overlooked (but super important) parts of getting onto Medicare. I help every one of my clients with this because it can make a huge difference in your overall costs.

So whether you’re leaning toward Medigap + standalone drug plan or going with a Medicare Advantage plan that includes drug coverage, I’ve got your back.

Want personal help or just want to make sure you’re doing it right?

👉 You can request my free 2025 Medicare Workbook here:

That’s a wrap on Day 4!

You’ve got the basics of Medicare Part D down — what it covers, when you need it, and how to avoid those sneaky penalties.

Tomorrow, we’re jumping into a topic that surprises a lot of people: dental, vision, and hearing. Medicare doesn’t cover these the way you might think… but don’t worry, I’ll break it all down for you in Day 5.

👉 Click here to head to Day 5 — we’re almost at the finish line!