pillar · tools · retirement-income · tax-planning · social-security · medicare
Free Retirement Calculators: Quick Answers to the Questions Everyone Googles
Nine free, no-sign-up retirement calculators that each answer one real question — Social Security timing, RMDs, IRMAA, Roth conversions, state taxes, early retirement — then hand you into a full plan.
By Mindaugas Laucius · October 23, 2026 · Last reviewed October 23, 2026
Most people don't arrive at a retirement site wanting to build a 40-year financial model. They arrive with one specific question: When should I claim Social Security? What's my RMD this year? Will moving to Florida actually save me tax? Can I get at my 401(k) before 59½?
So we built a tool for each of those questions — nine free calculators, no sign-up, nothing to install, each answering one thing clearly and then handing you into the full plan when you want the whole picture. This page is the map: find your question, open the tool.
Find your question
| Your question | The tool |
|---|---|
| Which money deadlines are coming up for me — and when? | Retirement milestones by age |
| When does waiting to claim Social Security pay off? | Social Security break-even |
| Will I pay a Medicare surcharge — and can I appeal it? | IRMAA calculator + SSA-44 checker |
| How much must I withdraw for my RMD, and by when? | RMD calculator |
| Will my savings last at this level of spending? | How long will my money last? |
| How much can I convert to Roth before the next bracket or IRMAA tier? | Roth conversion headroom |
| How much would I save (or pay) in state tax by moving? | State-to-state tax comparison |
| What will health insurance cost until Medicare at 65? | Early-retirement health insurance bridge |
| Can I take money out before 59½ without the 10% penalty? | Rule of 55 + 72(t) |
Below, the same nine grouped by topic.
Not sure which to open first? Match it to your stage. A decade or more out, the milestones tool and the money-last tool tell you whether you're on track and what's coming. Within five years of retiring, the Social Security break-even, Roth headroom, and IRMAA tools are where the consequential, hard-to-reverse decisions live. Already retired, the RMD and state-tax tools handle the recurring questions. Retiring early, before 59½, start with the Rule of 55 and the health-insurance bridge. The tools hub has a "where are you?" picker that reorders them for your stage.
Planning ahead: what's coming, and when
Retirement is a series of dated deadlines — catch-up contributions, the 59½ penalty wall, Social Security windows, Medicare sign-up, IRMAA's two-year lookback, and RMDs. Miss one and it can cost real money. Retirement milestones by age takes your birth month and year and lays out every age-based money deadline from 50 to 75, dated to the month with a countdown to each, so nothing sneaks up on you.
Social Security & Medicare: the timing questions
Two of the biggest irreversible decisions in retirement are when to claim Social Security and how to keep Medicare from surcharging you.
The Social Security break-even calculator compares claiming at 62, your full retirement age, and 70 — showing the monthly check at each age, the lifetime totals in today's dollars, and the age each later claim catches up and passes an earlier one. Waiting isn't automatically right, but it helps to see the trade-off in dollars before deciding.
Cumulative Social Security by claim age.
Cumulative lifetime Social Security benefits for a worker with a $3,000/month Primary Insurance Amount at full retirement age (67), claimed at 62, 67, or 70. The dashed verticals mark the break-even ages — where claiming later finally overtakes claiming earlier.
View data table
| Age | Claim at 62 ($2,100/mo) | Claim at 67 ($3,000/mo) | Claim at 70 ($3,720/mo) |
|---|---|---|---|
| 62 | $0 | $0 | $0 |
| 67 | $126,000 | $0 | $0 |
| 70 | $201,600 | $108,000 | $0 |
| 75 | $327,600 | $288,000 | $223,200 |
| 79 | $428,400 | $432,000 | $401,760 |
| 80 | $453,600 | $468,000 | $446,400 |
| 83 | $529,200 | $576,000 | $580,320 |
| 85 | $579,600 | $648,000 | $669,600 |
| 90 | $705,600 | $828,000 | $892,800 |
| 95 | $831,600 | $1,008,000 | $1,116,000 |
Source: SSA — Retirement Benefits: Effect of Early or Delayed Retirement · Last reviewed May 26, 2026
The IRMAA calculator + SSA-44 checker answers the Medicare half: it takes your income and tells you whether you'll owe the Income-Related Monthly Adjustment Amount — the surcharge on Medicare Part B and Part D for higher earners — how far you are from the next tier, and, crucially, whether a life-changing event lets you appeal it with Form SSA-44. For the why behind it, see the IRMAA cliff explained.
Withdrawals: how much, and will it last
Once you're drawing down, two questions dominate. The RMD calculator finds your required-minimum-distribution start age (73 or 75, depending on your birth year), this year's required amount from the IRS Uniform Lifetime Table, the April 1 first-year deadline trap, and a 10-year projection.
The bigger-picture question — will my savings actually last? — is what How long will my money last? answers, and it's the one tool here that runs the full 10,000-path simulation in your browser: the chance your money lasts to 85, 90, and 95 at your spending level, plus a button that solves for the spending that gives you 90% odds. (If the idea of 10,000 simulated futures is new, here's why that beats a single projection.)
Taxes: conversions and location
Two levers quietly move your lifetime tax bill more than almost anything else. The Roth conversion headroom calculator shows how much you can convert in a given year before you spill into the next federal bracket or trip a Medicare IRMAA tier — and it includes the new $6,000 senior deduction and its phase-out. The state-to-state tax comparison estimates what your pension, IRA withdrawals, and Social Security would be taxed in any two states, so a potential move becomes a number instead of a guess. (The full picture of who taxes what is in our 2026 state map.)
Retiring early: the before-59½ questions
Leaving work before the normal milestones raises two specific problems. The early-retirement health insurance bridge estimates what coverage costs from your retirement date to Medicare at 65 — COBRA, then ACA marketplace premiums after the 2026 premium tax credit, and how your income choices swing the bill. The Rule of 55 + 72(t) calculator checks whether you can tap retirement accounts before 59½ without the 10% penalty, and sizes 72(t) substantially-equal payments. Both pair with our full guide, how to retire at 55 without the penalty.
When you want the whole picture
Each tool answers one question. When you're ready to see how the answers fit together — how claiming, converting, spending, and market luck interact across a 40-year retirement — the full Yearfold calculator runs 10,000 simulated futures on your actual plan, and most tools carry what you've entered straight into it. You can also browse all the free tools in one place, or read how the engine works.
Not sure you even need to keep working? Start with do you already have enough to retire?
Frequently asked questions
Are these retirement calculators really free? Yes. All nine are free, need no sign-up or account, and run in your browser. Your exact numbers aren't stored or sent anywhere — we only count anonymous, rounded usage, such as an age band, to see which tools help. The one exception is opt-in: if you ask the milestones tool for email reminders, we keep your email and birth month and year.
Which retirement calculator should I start with? Start with the question on your mind. If you're choosing when to claim Social Security, use the break-even tool. If you just turned 63, check IRMAA and Roth conversion headroom. If you're eyeing an early exit, start with the Rule of 55 and the how-long-will-my-money-last tool. The milestones tool is a good first stop if you're not sure what's coming.
How accurate are the calculators? Each uses the official 2026 figures (IRS, SSA, CMS) and cites its primary sources with the date its rules were verified. They're educational estimates, not personalized advice, and they simplify some rules — each tool notes where. For a full probabilistic plan, the main calculator runs 10,000 market simulations.
Do the free tools replace the full retirement calculator? No — they answer one question each. The full calculator ties everything together and runs 10,000 simulated market futures to show the probability your money lasts. Each tool links to it, and most carry over what you've already entered.