If you're not checking your mailbox and inbox a little bit more closely, you should be—at least for the next few weeks.

That's because January is the start of tax season, and most of the vital forms you need to file your 2024 return should be en route soon, if not already in your hands.

Today, we're going to review exactly which documents you should be looking for, then showcase a little outside expert insight into what to expect (and what can go wrong).

The Tea

The U.S. Internal Revenue Service—aka the IRS, aka Uncle Sam, aka the tax man, aka Mike Rotunda in select circles—has more than 800 tax forms and schedules that are used to report tax and other financial information.

Fortunately, the average person really only needs to worry about a handful of those.

Young and the Invested Tip: Is 2025 the year you'll start taking your retirement plan seriously? Sign up for our free weekly letter, Retire With Riley, to gain the know-how you need.

Below is a helpful checklist of tax forms that regular taxpayers are likely to receive and need to file, courtesy of the Illinois CPA Society. This pairs well with our tax preparation checklist.

Importantly, while we list 14 forms here, many (lucky!) taxpayers only deal with one or two of these. Please read the descriptions to better understand which of these forms you should expect.

W-2: Provided by employers annually to report an employee's total compensation, taxes paid, and contributions to retirement accounts, among other payroll deductions and details.

1098: The mortgage interest statement provided by each lender for each mortgage a taxpayer is named on, reporting how much was paid in interest, insurance premiums, and other financial details. You will receive this if you purchased a new property or continued paying an existing mortgage in 2024.

1098-E: Reports federal student loan interest paid by borrowers equal to or greater than $600. Taxpayers with federal student loans will likely see this one.

1098-T: Issued by educational institutions to taxpayers who received payments for qualified tuition and expenses, certain adjustments, scholarships, or grants.

1099-B: Reports capital gains or losses. Issued by each applicable financial institution to taxpayers with proceeds from broker or barter transactions, like selling stocks or options, or exchanging property.

1099-DIV: Reports dividends or other distributions from investments during the calendar year. Issued by each applicable bank or financial institution.

1099-INT: Reports any interest above $10 for each interest-bearing account from each applicable bank or financial institution.

1099-K: Reports income received for sales through payment networks like Cash App, eBay, Etsy, PayPal, and Venmo, among others. Taxpayers with these types of transactions can expect to receive a 1099-K from the third parties where their transactions exceeded $5,000 in 2024.

1099-MISC: Reports income earned from miscellaneous sources, like royalties, rents, prizes, awards, or other non-employee compensation.

1099-NEC: Reports income for independent contractors. Independent contractors earning more than $600 in the calendar year from an entity will receive a 1099-NEC from each applicable entity. However, if an independent contractor is organized as an incorporated entity (i.e., LLC, S Corp, or C Corp), they generally won't receive these forms. It doesn't mean people / businesses won't send them anyway, but incorporated contractors are not obligated to nor will they get in "trouble" with the IRS if they don't provide them.

1099-R: Reports income from a pension, annuity, retirement account, profit-sharing plan, or insurance contract. Issued by each applicable financial institution when distributions are $10 or more in a calendar year.

Schedule K-1: Reports the amounts (income, losses, etc.) that are passed through to each party that has an interest in certain entities (i.e., business partnerships, LLCs that have at least two partners or elect to be taxed as corporations, S corporations, and trusts and estates) that must be reported on their own tax returns. Three groups of taxpayers typically receive a K-1: business owners, co-owners, and partners; shareholders and investors; and those receiving income or assets from a trust or estate.

SSA-1099 or SSA-1042S: Reports total Social Security benefits received. Taxpayers will receive either Form SSA-1099 or Form SSA-1042S from the Social Security Administration.

As usual, the deadline for filing 2024 individual tax returns is April 15, 2025. However, many tax deadlines have been pushed back for people who lived in states impacted by Hurricanes Helene and Milton in 2024. (Not sure about your status? Check out the IRS's page outlining disaster-related tax relief.)

The Take

Of course, you need to know more than just which forms to look out for. You'll also want to know when to expect your tax forms, what happens if you don't receive them, how long to keep them, and more.

This week, we sat down with Mark Gallegos, tax partner at PorteBrown LLC, to get the answers to those questions:

Young and the Invested (YATI): When should people expect to receive most of these tax forms?

Gallegos: Some of these—1099s, W-2s, others—are being prepared right now, but most of these, by law, should be received by the end of January.

YATI: Are there any oddballs? Any forms that you get them sometime that isn't the end of January?

Gallegos: Well, the 1099, forms. 1099-DIV, 1099-INT, and so on. They're coming from, let's say, Charles Schwab or Morgan Stanley. Feb. 15 is when you typically see these forms. 

Young and the Invested Tip: Did your investments do well this year? Were they terrible? Either way, you'll want to know how capital gains taxes work.

But you'll typically send out tranches of them over time. Some will be the end of January, some will be the middle of February. These firms can even get extensions to send them out by the end of February, and then, unfortunately, sometimes in March, they're sending corrected 1099s.

YATI: It sounds like people should wait a bit if they're receiving 1099s to make sure they have the final, correct one.

Gallegos: I'll have clients that, by the time mid-March comes, they'll hand me three different Charles Schwab statements for the same account, and here's one dated Feb. 5, here's another dated Feb. 20, and here's another one dated March 5. Something has changed on each one, but it's usually just a couple dollars. Nothing drastic, but unfortunately, you have to put down accurate information. The IRS only cares about whether you accurately reported your income and expenses, based on the information they have in their system.

Let's say you get a corrected 1099 for interest, and the figure is $1,000, and you don't put that on your tax return, you're likely going to get a matching notice from the IRS. It'll say, "Our records show that we received your return, but it has no interest income on there, and we have a 1099 for you that says you should have $1,000."

YATI: I'd imagine that even when these discrepancies are a little amount, these corrections could cause some stress, some worry that you're in real trouble.

Gallegos: People will get a letter in the mail from the IRS sometimes—and it always feels like they get these on a Friday, so on Friday night, I get these emails saying, "Oh my gosh! I'm getting audited! I owe all this money!" And I have to tell them, "No, you're not getting audited. You received a matching notice that says you owe money." 

Even then, the letter might say you owe $2,000 in taxes, penalties, and interest, but I can tell you, whatever the number is, a lot of times, people don't actually owe that money. A lot of times there's just an error—perhaps you didn't get credit for a line you should have—and we review the filing, see where the issue is, then write back to the IRS and attach the supporting documentation to resolve it.

YATI: Do any other forms get sent out at different times?

Gallegos: Another form on there that often comes later than Jan. 31 is the K-1—a form you get if you're a partner in a partnership, or a shareholder of an S corporation, or the beneficiary of a trust that produces income that comes out of it. 

Tax returns for S corps and partnerships are due March 15, which means the K-1s can come out anytime between now and March 15. But business returns can be extended for six months, so while March 15 is the due date, they can be extended until Sept. 15. 

I have clients who would love to get their taxes done every year by April 15, but they can't because even though they have their 1099s, their 1098 mortgage interest, student loan interest statements, and so on, but they're not going to get their K-1s until the end of August or beginning of September. That means I can't file their individual tax return until sometime in the fall.

YATI: In the event that you don't get a form in a timely manner, is there a way to press the matter? You just have to wait for the forms to be able to file?

Gallegos: A lot of people don't always receive forms in a timely manner. The good news is, you can download a lot of tax forms now. You used to get every tax form in the mail. But now a lot of them are on digital platforms where you go to a website, log into your account, and download them.

Young and the Invested Tip: 90% of all taxpayers claim the standard deduction. But it isn't the same for everyone.

Still, I get calls all the time from clients saying, "It's Feb. 5. I haven't received my W-2 from my employer yet. What do I do about that?" And honestly, there's little more than you can do other than calling your employer. Shake the tree as much as you can. But depending on your organization, you may or may not want to do that. 

In theory, you could report them to the IRS …

YATI: … But that's a steep escalation, right?

Gallegos: Yes, right. 

Also, this all assumes your employer is still paying your paychecks normally—that this is just the W-2 you're missing so you can file. Your employer is supposed to have your W-2 out by Jan. 31, but again, there's not a whole lot you can do if it's a little late other than remind them.

YATI: And how do late forms impact when you pay owed taxes?

Gallegos: I've heard people say, "I think I'm going to owe $50,000, so we'll just pay $50,000, and if [that number] is off, then we'll true it up next year." 

The problem is, at some point in time, the business is going to file the tax return and issue the K-1s, and the IRS gets a copy of those K-1s. So when you file your tax return, you'll have a discrepancy between what was filed on your return—you filed to the best of your knowledge, under the threat of penalties and perjury, but you have a document that's wrong.

Let's just say you put $50,000 of income when you file your return April 15. Then you get to September and you get the K-1 and it says you have $100,000 of income on there. You can't just pick up the difference next year. I have to, as an advisor, say that we should now amend your 2024 individual tax return and report the difference, then have you pay the tax on that. Or it could go the other way where you report $50,000 and it ends up being less. 

Whichever way it ends up going, in those situations, I say that you might as well wait to file. Because you can always extend your return. Individuals can extend until Oct. 15. 

But a tax extension is truly just an extension of time to file. That's it. It's not an extension of time to pay. So in a situation like the one we just talked about, where I have a client who doesn't have their K-1 and we're waiting, I tell them we need to get estimates of what that income will be [from whoever is producing the K-1], and then we run a projection. Maybe it comes out to $50,000. Then I'll tell you "We're going to file an extension to file, but you need to pay $50,000 by April 15." And then we'll pay your tax return in August, September, October. 

If you file late but don't pay the IRS, sure, you'll avoid late filing penalties, but you'll still have late payment penalties, as well as interest on the money you should have paid. And that adds up.

YATI: On the list of important forms, are there any forms you think are missing—forms that are fairly common to receive, but that didn't make it onto the CPA Society's list? 

Gallegos: No, it's a pretty thorough list. But I want to remind people about the 1099-K. 

1099-Ks are for when you receive payments through Cash App, Venmo, PayPal, those types of things. There's a requirement that once that number exceeds a certain threshold, these platforms need to report the transaction amounts to you. The rules are phasing in lower amounts—you'll only get a 1099-K if you receive more than $5,000 in transactions for 2024, then more than $2,500 in 2025, and more than $600 in 2026.

Young and the Invested Tip: Social Security benefits absolutely can be taxed. Here's how you can sidestep those taxes.

We started to see more of these last year, I think you'll see even more this year, and it will become more prevalent in the years to come.

Young and the Invested: One last question. Is there any advice you have for people about how to handle and preserve their tax documents from one year to the next?

Gallegos: I always say to keep your tax returns forever, but you only need to keep your tax supporting documents—your 1099s, etc.—for seven years, then destroy them. 

The statute of limitations is three, meaning the IRS has three years from the time you file to audit you or have you amend. Still, seven years is a good rule of thumb. 

However, again, keep your tax returns forever. You won't always need them. But maybe in the future you're getting a mortgage, buying a business, and a lender might ask for something like the last 10 years of your tax returns. 

Riley & Kyle

Young and the Invested

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