The organising insight: a tax break can sit in three places. Once you see this, every account type becomes easy to classify and impossible to confuse.
- On the way in — a deduction or an exclusion from income. A traditional 401(k) deferral never appears in your taxable wages; a deductible traditional IRA contribution reduces adjusted gross income; an HSA contribution is deductible, and if made through an employer's payroll it also escapes Social Security and Medicare tax, which no other account can do.
- During the holding period — no annual tax on interest, dividends or realised gains. This applies to essentially every account in the category, and it is the quietest of the three benefits: it removes the yearly tax drag and lets you rebalance or sell a position without a tax consequence.
- On the way out — qualified withdrawals that are not taxed at all. A Roth IRA or Roth 401(k) delivers this; so does a 529 plan when the money pays qualified education expenses, and an HSA when it pays qualified medical expenses.
Now the classification writes itself. A traditional 401(k) or traditional IRA has breaks one and two, with ordinary income tax on the way out. A Roth account has breaks two and three, with no deduction going in. A 529 plan has breaks two and three federally, and many states add a deduction going in. A health savings account has all three — deductible in, untaxed growth, tax-free out for medical costs — which is the single most useful fact in this entire category, and the reason an HSA is often the account to fund before anything except an employer match.
The consistent trade: the break is paid for with restriction. Every account in the category limits how much you can contribute each year, and most limit who may contribute at all — earned income requirements, income phase-outs, employer sponsorship, or enrollment in a qualifying high-deductible health plan. Most also limit what the money may be used for, and enforce that limit with a penalty on top of ordinary income tax: withdrawals before age 59½ from a retirement account, non-medical withdrawals from an HSA before 65, or 529 earnings not spent on education. Several impose required minimum distributions, and a flexible spending account goes further and forfeits unused money at year end. When you compare accounts, the useful question is not "which has the best tax treatment" but "which restriction am I willing to accept for it."
A typed index of the category — each of these has its own page, with its own limits and rules:
Retirement, employer-sponsored: the 401(k) and the 403(b), the 457(b) for government and some nonprofit employees, and the Thrift Savings Plan for federal employees and service members.
Retirement, individual: the traditional IRA and the Roth IRA, both forms of the individual retirement arrangement.
Health: the health savings account, and the flexible spending account for those without a qualifying high-deductible plan.
Education: the 529 plan, and the Coverdell education savings account.
Disability: the ABLE account, for beneficiaries whose qualifying disability began before the age of onset set by statute.
What you give up relative to a taxable account. A regular brokerage account has no contribution limit, no eligibility test, no purpose restriction and no early-withdrawal penalty, and it carries three tax features the accounts above do not: long-term capital gains and qualified dividends taxed at preferential rates rather than as ordinary income, the ability to harvest losses against gains, and a step-up in basis at death that can erase a lifetime of unrealised gain for heirs. That is why a good plan usually holds both, and why deciding which assets belong in which account — asset location — is a real question rather than an afterthought.