Permanent
Delaying Part B when your employer plan pays second
If your employer is below the size threshold, Medicare pays first whether or not you enrolled. Claims processed on the assumption Medicare already paid can leave you owing the difference, applied backwards over months. A Part B penalty can also attach and generally stays for as long as you have Part B.
Permanent
Letting a Medicare Supplement go and expecting to return
There is a period when you first become eligible during which a Supplement must be issued regardless of health. Outside it, an insurer may apply medical underwriting and may decline.
Permanent
Going without creditable drug coverage
A late-enrollment penalty can attach and generally persists. "Creditable" is the operative word — some employer and union coverage counts and some does not, and the plan must tell you which in an annual notice. Keep it.
Hard to reverse
Cancelling before the replacement is confirmed
Cancel first and you can create a gap no window will let you close. Enrolling in a replacement usually ends the old plan automatically; manual cancellation is rarely necessary and frequently harmful.
Hard to reverse
Missing a Special Enrollment Period
The clock generally runs from the qualifying event, not from when you noticed one existed. Miss it and you may wait until the next annual window with nothing in between.
Hard to reverse
Guessing high on a Marketplace income estimate
Advance credits are reconciled against actual income at tax time. It is arithmetic rather than a penalty, but it arrives more than a year later, long after anyone remembers the conversation.
Fixable
Choosing on monthly cost alone
The commonest mistake and the least damaging, because it usually corrects at the next window — unless it costs you a doctor mid-treatment, at which point it stops being fixable.