Brand-Name Drugs and Part D: Why the Cheapest Plan Is Still the Safe Bet
Taking a brand-name drug? In 728 drug lists, the lowest-premium Part D plan was usually the best and never cost more than about $400. How to read the labels.
October 24, 2026
Articles
Retirement planning insights from the WhenIm64 team.
For 3 in 4 People, the Lowest Part D Premium Wins
For about 3 in 4 people, the lowest-premium Part D plan is the right one. The one check for your situation, how exceptions work, and the cost of picking wrong.
October 24, 2026
Medicare Open Enrollment Starts October 15: Make the Decision That's Hard to Undo First
Open enrollment runs October 15 to December 7. The first decision, Medicare Advantage or Medigap, is the one that's hard to undo. What changed for 2027 and which states let you switch back.
October 4, 2026
Open Enrollment Starts October 15: Don't Let Your Drug Plan Auto-Renew
If you do nothing by December 7, your Part D plan renews at its 2027 price. Deductibles on every national plan, what expensive plans really buy, and the hidden cost of switching.
October 4, 2026
Why is Choosing a Medicare Part D Plan So Complicated?
I tried to build a straightforward Medicare Part D plan chooser for WhenIm64. What I discovered instead was a maze of hidden pricing, fine print deductible rules, and a government plan finder that leaves out the one number that matters most.
March 28, 2026
The HSA: The Best Retirement Account You're Probably Using Wrong
Most people treat their HSA like a medical debit card — spend it, reset it, repeat. But used correctly, the HSA is the only account in the tax code that gives you three tax breaks at once: no tax going in, no tax on growth, and no tax coming out. Here's what I wish I had known before I retired, including the one move almost nobody knows you can make once you leave your employer.
March 17, 2026
The IRMAA Nightmare Nobody Warned Me About
I did my homework before retiring. It still wasn't enough.
March 8, 2026
Something I Learned the Hard Way About HSAs and Medicare
My employer knew about the HSA and Medicare enrollment trap. I had to find out the hard way.
March 8, 2026