30 plain-English guides
Find the guide for what just happened
Pick the life event. Each guide explains the tax rules that apply, the IRS procedures that matter, and what to do next.
Start Here
A map of the IRS problems that follow a life upheaval, and where to begin.
Job Loss
Layoffs, severance, unemployment benefits, and the retirement money people reach for.
Cashing Out a 401(k) After a Layoff: The Tax Bill Nobody Mentions
When the paychecks stop, the 401(k) looks like an emergency fund. Before you request that check, understand the withholding, the 10% additional tax, and the exceptions that may apply.
Read the guideYou Lost Your Job and Owe the IRS: What to Do First
Owing the IRS while you are out of work feels impossible. It is not. There is an order of operations, and following it keeps a temporary setback from becoming a ten-year problem.
Read the guideSeverance Pay and Taxes: Why the Withholding Often Falls Short
A severance check feels like a cushion. The IRS sees a wage payment, and the flat withholding rate your employer uses may leave you short when you file.
Read the guideUnemployment Benefits Are Taxable: How to Keep Them From Becoming an IRS Bill
Losing a job is bad enough. Finding out in April that your unemployment checks were taxable, and nobody withheld a dime, is worse. Here is how to see it coming.
Read the guideMedical Crisis
Serious illness, medical bills, HSAs, and the deadlines that keep running while you are in the hospital.
Using Your HSA in a Medical Crisis Without Creating a Tax Problem
A health savings account is the best money you have when a medical crisis hits, if you use it the way the law allows. Spend it on the wrong thing and the IRS adds 20%.
Read the guideThe Medical Expense Deduction After a Health Crisis: What Actually Counts
A year of hospital bills can open up a deduction most people never use. The floor is high, the rules are specific, and the records matter more than the receipts you remember.
Read the guideUsing Retirement Money for Medical Bills: What the 10% Exception Covers
When the hospital bills arrive, the retirement account is often the only money left. Some of it may come out without the 10% additional tax. None of it comes out tax free.
Read the guideSerious Illness and IRS Deadlines: What Happens When You Physically Could Not File
The IRS calendar does not stop for a diagnosis. But the rules do account for people who were too sick to deal with paperwork, if you know which rule to use and what proof it needs.
Read the guideSettled Your Debts After a Crisis? The 1099-C and the Insolvency Exclusion
You finally settled the credit cards that piled up during the crisis. Then a Form 1099-C arrives and says the forgiven part is income. It may be. It may also be excludable.
Read the guideDisability
Disability income, SSDI back pay, loan discharges, and getting the IRS to work with you.
The Disability Exception to the 10% Early Withdrawal Tax: Meeting the 72(m)(7) Test
If a disability has ended your ability to work, the 10% additional tax on early retirement withdrawals may not apply. The test is strict, and it is not the same as being unable to do your old job for a while.
Read the guideIs Your Disability Income Taxable? It Depends on Who Paid the Premiums
Two people can receive identical disability checks and owe completely different taxes. The difference is usually decided years earlier, by who paid for the policy and with what kind of dollars.
Read the guideStudent Loans Discharged for Disability: Is the Forgiven Amount Taxable?
A total and permanent disability discharge can wipe out tens of thousands in student loans. Federal law excludes it from income, but the rule changed for discharges after 2025, and one missing number can cost you.
Read the guideSSDI Back Pay and Taxes: The Lump-Sum Election That Can Shrink the Bill
After years of waiting, Social Security finally approves the claim and pays the back benefits in one check. The tax law lets you treat that money as if it arrived on time, if you know to ask.
Read the guideDealing With the IRS When You Have a Disability: Tools Most People Never Hear About
A disability can make the ordinary parts of dealing with the IRS hard: reading notices, making calls, signing returns. The IRS has tools for each of those. Here is where to find them.
Read the guideNatural Disasters
How IRS disaster relief is announced, casualty losses, insurance money, and lost records.
Deducting Disaster Damage: How the Casualty Loss Rules Work Now
A flood or fire can wipe out a home and everything in it. The tax code lets you deduct some of that loss, but only for declared disasters, only after insurance, and only if you can prove the numbers.
Read the guideClaiming a Disaster Loss on Last Year's Return to Get Cash Sooner
After a disaster, money now is worth more than money next April. Section 165(i) lets you move the loss back a year and amend for a refund while you are still rebuilding.
Read the guideWhen the Insurance Check Is a Taxable Gain: Disaster Payouts and Section 1033
It sounds backwards, but a disaster can create taxable income. If insurance pays more than you originally paid for the property, you may have a gain, unless you use the rules that postpone or exclude it.
Read the guideIRS Disaster Relief: How Deadline Postponements Are Announced and Who Gets Them
After a hurricane, wildfire or flood, the IRS usually pushes back filing and payment deadlines for the area. Knowing how that relief is announced, and whether it covers you, keeps you from missing it.
Read the guideTapping Retirement Money After a Disaster: Qualified Disaster Recovery Distributions
After a federally declared disaster, the retirement account may be the fastest money you can reach. A special rule lets you take up to $22,000 without the 10% add-on, spread the tax, and even put it back.
Read the guideYour Tax Records Were Destroyed in a Disaster. Now What?
The flood took the filing cabinet along with everything else. You still need records to claim a loss, answer a notice or file this year's return. Most of them can be rebuilt.
Read the guideIncarceration
Filing from inside, powers of attorney, and the tax debt waiting at release.
Filing Taxes While Incarcerated: What Still Applies Behind Bars
A prison sentence changes almost everything, but not the Internal Revenue Code. If you had income, or a refund is waiting, the filing rules still apply. Here is how to handle them from inside.
Read the guideComing Home to an IRS Problem: Tax Debt and Unfiled Years After Release
Release day is about housing, work and family. Somewhere in the pile of things to deal with is the IRS. The first step is finding out exactly what it thinks you owe.
Read the guideHandling Taxes for a Family Member in Prison: Forms 8821, 2848 and Signing Returns
When someone you love is incarcerated, the IRS mail often lands on your kitchen table. The IRS will not talk to you about it unless the right form is on file. Here is which one, and what it lets you do.
Read the guideGambling Winnings
W-2G forms, withholding, losses, and jackpots that turn into tax bills.
Deducting Gambling Losses: The New 90% Rule and the Records That Prove It
For years the rule was simple: deduct losses up to your winnings. Starting with 2026, the law allows only 90% of your losses. A gambler who breaks even can now owe tax.
Read the guideGambling Winnings and the IRS: Form W-2G, Withholding and the Bill That Follows
A big night at the casino or a lucky parlay feels like free money. The IRS sees taxable income, and the casino may have withheld less than you will owe.
Read the guideYou Won the Lottery. Here Is How Jackpots Turn Into IRS Problems
A jackpot is a life event in every sense. The tax side is simple to state and easy to get wrong: the withholding is not the tax, the clock starts when you claim, and splitting the prize needs paperwork.
Read the guideMoving
Address changes, moving costs, and selling a home early because life changed.
Moved and Missed the IRS Mail? Your Last Known Address and Why It Matters
After a move, IRS mail keeps going to the old address. The law says that is usually good enough. If a deadline passes while the notice sits in someone else's mailbox, you may live with the result.
Read the guideMoving for a New Start? Why Your Moving Costs Are Probably Not Deductible
People move after a job loss, a divorce, an illness or a disaster. Many assume the move is deductible, or that the employer's relocation money is tax free. For most people, neither is true anymore.
Read the guideSelling Your Home Early Because Life Changed: The Partial Home Sale Exclusion
The full home sale exclusion requires two years of ownership and use. Life does not always give you two years. If a job change, health problem or unforeseen event forced the sale, a partial exclusion may still apply.
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