Smart retirement decisions, one step at a time
Four short guides on choices that affect each other: when withdrawals must start, whether to convert to a Roth, when to claim Social Security and how Medicare premiums are set.
Prepared by Prem Tax and Accounting Corp. Last reviewed November 6, 2026. Figures as of November 6, 2026.
Retirement choices push on each other. Money you take from an IRA raises your income. Your income decides how much of your Social Security is taxed, and it sets your Medicare premium two years later. So we look at the four choices together, one short guide for each. The One Big Beautiful Bill Act, or Public Law 119-21, left the required minimum distribution (RMD) rules, IRA limits, Roth conversion rules and the way Social Security is taxed as they were. It added a temporary deduction for people 65 and older, which we explain in our senior deduction guide.
Required minimum distributions and the ages that matter
When required minimum distributions start (73 or 75), how the amount is figured, the 25 percent penalty, charity transfers and the key ages from 50 to 75.
Read →Roth conversions and tax brackets: how much room do you have?
How a Roth conversion is taxed, why permanent 10 to 37 percent rates help planning, 2026 and 2027 bracket tops and effects on Social Security and Medicare.
Read →When to claim Social Security: the rules that shape the choice
Claiming ages from 62 to 70, full retirement age, the earnings limit, the 3.6 percent 2027 increase and how benefits are taxed, with no one-size-fits-all age.
Read →Medicare enrollment and IRMAA: the dates and the income test
Medicare's seven-month sign-up window, late penalties, the HSA stop rule and IRMAA surcharges, with 2026 premiums and a labelled 2027 planning figure.
Read →What is not out yet
The IRS has not published 2027 limits for 401(k) plans, IRAs or charitable transfers from IRAs as of November 6, 2026. Medicare has not published 2027 Part B premiums or the income-based surcharges. The Social Security Administration has published its 2027 numbers. We update each guide when the official figures appear. Our 2027 figures page tracks what is out, and the 2026 tax brackets are on their own page.
If you are still saving rather than spending, see our retirement plan guides.
Common questions
Does Illinois tax retirement income?
Illinois residents can subtract the federally taxed part of qualified plan and IRA payments, including amounts converted to a Roth IRA, and Social Security benefits. It does not let you subtract private nonqualified deferred pay, third-party sick pay or income taxed under federal ten-year averaging. Other states differ, so check yours on our [state taxes](/state-taxes/) page.
Where do I start?
Start with the guide that matches your next milestone: RMDs at 73 or 75, Social Security near 62 and Medicare near 65. If you plan a large IRA withdrawal or conversion, read all four, because one move changes the others.
Official sources
- IRS: Retirement topics, required minimum distributions
- SSA: 2027 cost-of-living adjustment fact sheet
- Medicare.gov: when can I sign up for Medicare
Keep reading
- Required minimum distributions and the ages that matter
- Roth conversions and tax brackets: how much room do you have?
- When to claim Social Security: the rules that shape the choice
- Medicare enrollment and IRMAA: the dates and the income test
- Senior, tips, overtime and car-loan interest: what you can actually claim
- The 2027 numbers: published, computed or still to come
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