March 2025
The information in this article is considered accurate as of its publication date (March 2025). Tax laws and figures change regularly, so please reach out to confirm how current rules apply to your situation.
One of the most common reasons tax returns get delayed — or filed with errors — is missing documents. Some arrive in the mail in January. Others you have to track down yourself. A few you might not even realize are taxable.
This isn't a legal document; think of it as a starting checklist. Not every item will apply to you, and your situation may have things that aren't on this list. But working through it before you sit down to file will save you time and reduce the chance something falls through the cracks.
Before anything else, make sure you have the basics:
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These are the documents that most commonly slip through the cracks — either because people didn't know the income was taxable, didn't realize they'd receive a form, or simply forgot about the activity.
Unemployment income. It's fully taxable at the federal level and most states follow suit. If you received unemployment at any point during the year, you'll have a 1099-G. Many people assume it isn't taxable because it doesn't feel like a paycheck. It is.
Side income paid through apps. Venmo, PayPal, Cash App, and similar platforms are now required to report business payments to the IRS. Even if you don't receive a 1099-K, income from side work — selling goods, freelancing, services — is taxable regardless of how it was paid.
Cryptocurrency transactions. Selling, trading, or using crypto to purchase goods or services is a taxable event. If you had any crypto activity, you need records of your cost basis and sale prices for every transaction. Many exchanges now issue 1099-DA or similar forms, but the records are your responsibility.
RSUs and stock options. If your employer compensates you with restricted stock units or options, the income is reported on your W-2 when shares vest or options are exercised — but the 1099-B from the subsequent sale shows the full proceeds. Without the cost basis information from your employer, it looks like the entire sale was a gain. This mismatch causes errors and overpayments more often than almost anything else.
Estimated tax payments. If you made quarterly estimated payments during the year, you need the total amount you paid. The IRS has records, but they don't pre-populate this on your return. If you can't remember what you paid, check your bank statements or your IRS online account.
HSA distributions used for non-medical expenses. If you withdrew from an HSA for anything other than a qualified medical expense, that distribution is taxable and subject to a penalty. The 1099-SA will show the distribution; you need to know what it was used for.
A state tax refund from last year. If you itemized deductions in the prior year and then received a state refund, that refund may be partially taxable federally. You'll receive a 1099-G from your state.
Gambling winnings. Casinos, lotteries, and sports books are required to report winnings above certain thresholds on a W-2G. But all gambling winnings are technically taxable — even amounts below the reporting threshold. If you won and didn't get a form, that doesn't mean it's not income.
Sale of a home. If you sold your primary residence, most of the gain is likely excludable (up to $250,000 single / $500,000 married), but you still need to report the sale. You'll also want records of your original purchase price, capital improvements over the years, and closing costs from both the purchase and sale.
Foreign accounts or assets. If you have a financial account in another country with a balance exceeding $10,000 at any point during the year, you're required to file an FBAR (FinCEN 114) separately from your tax return. Additional FATCA reporting may apply depending on asset values.
Gathering documents is only half the battle — knowing which questions to ask is the other half. Our client organizers are designed to walk through your full financial picture before we begin preparing your return: every income source, every potential deduction, every life change that might affect your taxes.
That process isn't just a checklist. It's a conversation. If something in your organizer suggests a document you haven't received, we flag it. If a situation you describe might have tax implications you weren't aware of, we ask. The goal is to make sure nothing that should be on your return gets left off — and nothing gets included that doesn't belong.
If you're filing with us this year, your organizer is your starting point. Fill it out as thoroughly as you can, and we'll take it from there.
Questions about what to gather for your specific situation? Contact us — we're happy to point you in the right direction before you even start.