If you're inside five years of retirement, the highest-value thing you can do has nothing to do with your contribution rate. The real answer to what to do 5 years before retirement is to learn the calendar the IRS and the Social Security Administration run between 60 and 65. Five windows open during that band, and most of them close for life at 65. For a pre-retiree with $400,000 to $700,000 saved, working all five plus the two one-way elections at the end is worth roughly $400,000 to $500,000 in lifetime value, without saving an extra dollar.
The super catch-up disappears the year you turn 64
If you're 60, 61, 62, or 63, your 401(k) limit is higher than your statement probably shows. The 2026 base limit is $24,500, and anyone 50 and older gets a standard catch-up on top of it. Secure 2.0 replaces that standard catch-up with a super catch-up of $11,250 during those four years, bringing the total to $35,750 a year.
The year you turn 64, you're back to the standard limit. Four years of that extra $11,250 is $45,000 of tax-deferred money you couldn't otherwise contribute, worth about $67,000 by age 70 at a 7% return. The deduction lands right away: $2,475 a year in the 22% bracket, $2,700 in the 24%, $3,600 in the 32%.
Two wrinkles. If you earned more than $145,000 last year, the catch-up has to go into a Roth account instead. Same money, same limit, taxed now instead of later. And plans don't enroll you automatically, so tell HR before January of the year you turn 60 or you've already lost one of your four years.
Your HSA stops the day Medicare starts
The health savings account is the only triple tax advantaged account in the tax code. Money goes in pre-tax, grows tax-free, and comes out tax-free for a qualified medical expense. No other account does all three, which makes an HSA dollar worth more than a 401(k) dollar. Max it out first.
For 2026, self-only coverage allows $4,400 and family coverage allows $8,750, with another $1,000 at 55 or older. Five years on a family plan at $9,750 comes to $48,750 compounding tax-free for life. After 65 the list of qualified expenses widens to Medicare Part B, Part D, and Advantage premiums, plus dental, vision, and long-term care insurance, so the account becomes your medical bank account for the rest of your life.
The deadline is Medicare enrollment, usually at 65. From that day you can never contribute again. There's a six-month look-back too. Delay Medicare past 65 and Part A covers you retroactively for six months, so contributions have to stop six months before coverage begins.
The Roth conversion runway
Between the day your W2 income stops and the day RMDs start at 73 or 75, you decide how much taxable income you have. That's the biggest tax lever in these five years. Once RMDs hit, the IRS forces out 3.3% to 6% of your traditional accounts every year, stacked on top of your other income, which can raise the tax on your Social Security and trigger IRMAA Medicare surcharges.
Before then you control the dial. In 2026 the 12% bracket for a married couple ends at $100,800 of taxable income, the standard deduction is $32,200, and the new senior bonus deduction adds $6,000 per person, good through 2028. A retired couple at 65 can move roughly $148,000 a year out of a traditional account and stay inside the 12% bracket. Convert $80,000 a year for seven years and you've moved $560,000 for about $67,200 in tax. Leave it and let RMDs push you into the 24% bracket, and the same money costs about $134,000, with higher Social Security taxation and IRMAA on top.
Set this up early. Roth withdrawals follow a five-year clock from your first contribution, so open one now if you don't have it. On an ACA marketplace plan, watch the subsidy cliff near $86,000 a year for a couple. After 65, watch the IRMAA cliffs, which look back two years, so the return you file at 65 sets your Part B premium at 67.
Capital gains at 0%
The same low-income years open a second door. Long-term gains, on assets held more than 12 months, have their own rate schedule. For 2026 the 0% rate runs to $49,450 of taxable income for a single filer and $98,900 for a married couple, and a gain that keeps you under that line costs nothing in federal tax.
Take a 63-year-old couple who just retired with no income and $40,000 of traditional account withdrawals. After the $32,200 standard deduction, their taxable ordinary income is about $7,800, which leaves roughly $91,000 of room under the ceiling. They sell enough shares to book a $90,000 gain and owe no federal tax on it.
If they don't need the cash, they have two moves. They can buy the identical position back the next day at the same price, which steps their cost basis up to today's price and wipes 20 years of gains off the IRS's books. Or they can reposition, selling growth assets like an S&P 500 fund and buying income producers like dividend stocks, bonds, or REITs, with no tax on the sale.
Conversions and gains compete for the same bracket space. A $40,000 Roth conversion eats $40,000 of your 0% gain room, so sequence them. Heavy conversions for a couple of years, then heavy gain harvesting. The window closes when RMDs and Social Security lift your income above the 0% threshold.
Build the income floor while you still have a paycheck
The fifth window is about what you own when retirement starts. A 40% market drop in years one through three does permanent damage to a withdrawal-based plan, while the same drop in year ten is mostly recoverable. That's sequence of returns risk. If you planned to take 4% or 5% a year and the market falls 40%, the same bills now take closer to 9% of the portfolio, and you're selling shares at the bottom.
Research from retirement academics Pfau and Kitces in 2014 found that your bond and cash allocation should peak right at retirement and then decline through the phases that follow. They called it the bond tent. Build it in the five years before you retire, while a paycheck is still covering your bills.
Say you have a $1,000,000 portfolio, Social Security paying $24,000 a year, and expenses closer to $60,000. The gap is $36,000 a year, about $3,000 a month, and that's the income floor to build with income-producing assets: dividend stocks, treasury bonds, corporate bonds, multi-year guaranteed annuities, REITs, rental properties. Once that floor covers the bills, the rest can stay in equities. A 40% drop becomes something you read about in the news instead of something you recalculate every month.
Two decisions you only make once
The pension election is the first. The day you start the pension you pick single life or joint and survivor. Single life pays the most and stops the day you die. Joint and survivor pays 10% to 20% less and keeps paying your spouse, usually at 50%, 75%, or 100%. Once you sign, it's irrevocable, even if your spouse dies first. For a married couple the math usually favors the joint election, because there's a good chance one spouse outlives the other by eight to twelve years.
Claiming Social Security is the second. Delay to 70 and the check grows 8% a year, assuming you live long enough to collect on it. Claiming at 62 is a reasonable call for plenty of people, since it lowers what you withdraw from your accounts. Either way, the day you claim sets your check for life, so think through the repercussions before you sign.