What If I Haven’t Filed Taxes in Years? with Kevin Cross

Jun 20, 2025

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Did you hear about the guy who tried to pay his taxes with a smile? Unfortunately for him, the IRS still prefers cash.

All jokes aside, failing to file your taxes for several years is no small matter—but it’s not the end of the road, either. Kevin Cross joins us today with practical steps to help you get back on track.

Kevin Cross is a Certified Public Accountant (CPA) who has headed CPA firms in Florida and now Georgia. He has studied the tax code extensively and specializes in representing taxpayers before the Internal Revenue Service (IRS).

Start With the Present, Not the Past

The further you fall behind, the more difficult it is to catch up. But rather than beginning with the year you first missed, he recommends filing your most recent return first—say, 2024—and working backward as needed. This shows the IRS that you’re attempting to come into compliance, not ignoring your obligations.

Falling behind on taxes is more common than most people think. Life events like divorce, disability, job loss, or even the rise of gig work can trigger tax complications. For example, many gig workers receive a 1099 for the first time, try to file using online software, and are shocked to discover they owe thousands. Rather than seek help, they freeze—and the following year’s return also goes unfiled.

Of course, COVID didn’t help as many people have been struggling since then to get back on track.

Do You Always Have to File?

A common misunderstanding is that you must always file. If you’re not going to owe anything, you don’t have to file. That includes many senior citizens who live solely on Social Security.

However, if you're due a refund, you have up to three years to file and claim it. Miss that window, and the refund is forfeited.

Importantly, there’s a difference between not filing and not paying. Sometimes you don’t know what you owe—or if you owe—until you file.

Even if you don't owe taxes on the sale of a primary residence, for example, the IRS won't know that unless you file. If you don’t, you might receive a letter saying you owe thousands in capital gains tax—money you could’ve avoided paying.

How to Begin the Process

If you're unsure how many years you've missed, a good first step is to request a Wage and Income Transcript from the IRS. This document shows all your reported income—W-2s, 1099s, Social Security, retirement distributions, and more. You can request it through the IRS website by searching for “IRS wage and income transcript.”

Even with transcripts in hand, deciphering them can be complicated. That’s why we strongly recommend seeking help from a CPA or tax professional familiar with IRS representation. You may not know what to do with what you find. You can find a Certified Kingdom Advisor (CKA) in your area who specializes in tax planning and preparation by going to FaithFi.com and clicking “Find a Professional”.

Also, it’s helpful to know that the IRS’s own handbook, the Internal Revenue Manual, usually requires only the last six years of returns to be filed. That’s a helpful limit for those unsure where to begin.

The IRS Will Work With You

Don’t let fear keep you stuck. The IRS can work with you. Options include payment plans or even an offer in compromise, which may reduce your total tax liability.

Filing late taxes doesn’t have to be terrifying. With the right help and a step-by-step plan, you can get back on track—and even experience peace of mind. The IRS just wants to see you trying. Start with today, and take it one step at a time.

On Today’s Program, Rob Answers Listener Questions:

I have a TIAA retirement account from my husband's time as an adjunct professor at a local community college. It's a small amount. As I'm 76, I'm required to set aside a certain amount each year. I would like to give this to my son now so that those amounts can stay in the account and start accruing interest. Can I do that?
We have a credit card balance of $15,000 with an interest rate of 11%. We try to pay $2,000 a month, but the balance keeps increasing. Part of the reason is that our 29-year-old daughter, who lives and works in London, has a card on our account. We initially gave her the card for emergencies and plane tickets home, but she's using it for other expenses, such as occasional Ubers and travel. We want to pay off this card, but we're making no progress. What can we do?

Resources Mentioned:

Remember, you can call in to ask your questions every workday at (800) 525-7000. Faith & Finance is also available on Moody Radio Network and American Family Radio. You can also visit FaithFi.com to connect with our online community and partner with us as we help more people live as faithful stewards of God’s resources.

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