Tax filing checklist: documents, deadlines, and a smoother season

Tax season feels stressful when you’re hunting for documents, guessing which forms matter, or realizing (too late) that a key number doesn’t match what the IRS received. The good news: most of that stress is preventable with a simple, repeatable checklist.

Below is a practical system we use to help clients get organized quickly. You can follow it whether you’re filing an individual return, self-employed, a small business owner, or you’re somewhere in between. The goal isn’t perfection on day one—it’s to gather the right inputs so your filing is accurate, complete, and on time.

1) Start with last year’s return (and list what changed)

Before you collect documents, open your prior-year return and scan the big categories: income sources, deductions, and credits. This is your best clue for what to expect again this year. Then write down any life changes—these often drive the biggest differences in tax outcomes.

• New job, job loss, or a switch to contract work
• Marriage, divorce, or new dependents
• Buying or selling a home, or moving states
• Starting a business, side income, or a new rental property
• Large investment activity (stocks, RSUs, crypto, retirement distributions)

2) Gather identity + household information

This part is quick, but it prevents annoying rejections and delays. Have these ready for you, your spouse, and dependents.

• Full legal names and Social Security numbers
• Dates of birth
• Current address and phone number (and any prior address if you moved)
• Bank routing and account numbers (for direct deposit or payments)
• If you have dependents: school or childcare details if applicable

3) Collect income documents (most delays happen here)

Income is often reported to the IRS by third parties. If your return misses a form, it can trigger notices or adjustments later. When in doubt, gather more—not less—then sort it cleanly.

Employees and retirees

• W-2s from each employer
• 1099-R for retirement distributions
• SSA-1099 for Social Security benefits (if applicable)
• Unemployment statements (if applicable)

Self-employed, contractors, and side income

• 1099-NEC/1099-K/other 1099s from clients or platforms
• A clean income summary (monthly totals are ideal)
• Expense records (bank/credit card statements, receipts, invoices)

Investments and savings

• 1099-INT (interest)
• 1099-DIV (dividends)
• 1099-B (brokerage sales)
• Statements for RSUs/ESPP and other equity compensation (if applicable)

Rentals, partnerships, and other entities

• Rent received totals and expense records
• K-1s for partnerships, S-corps, or trusts

Crypto and digital assets (if applicable)

If you bought, sold, swapped, or received digital assets, gather the records now—this is one of the most time-consuming areas to reconstruct later. Even when platforms provide summaries, you still want supporting detail so cost basis and proceeds are consistent.

• Exchange transaction history or annual statement exports
• A list of wallets you used (if relevant)
• Records for transfers between exchanges (to avoid “missing basis” issues)
• If you received crypto as payment: invoices and USD value at receipt

The goal is clarity: what you acquired, what you disposed of, and what those amounts were worth. If you’re unsure which reports to pull, ask your preparer for the cleanest export format before you spend time manually copying data.

Multi-state moves and remote work (if applicable)

Remote work and mid-year moves can change your state filing needs. If you lived or worked in more than one state, gather details early so allocation questions don’t stall your return.

• Move dates and prior addresses
• Employer payroll details if withholding occurred in a different state
• Any notices or letters related to state filings (if you received them)

4) Track deductions and credits with documentation in mind

Deductions and credits can reduce what you owe, but the biggest difference between “good” and “great” recordkeeping is documentation. If you can’t explain a number with a statement, receipt, or summary, it becomes stressful later.

Common items to gather

• Healthcare coverage and related statements (if applicable)
• Student loan interest and tuition documents (if applicable)
• Childcare expenses and provider information (if applicable)
• Mortgage interest and property tax documents (homeowners)
• Charitable donations (with receipts/acknowledgements)

Self-employed and small business recordkeeping

If you have business income, the quality of your bookkeeping can be the difference between a quick, accurate return and a frustrating scramble. Even if you’re doing it yourself, aim for a clean set of monthly totals.

• Income summary by month (bank deposits or invoicing totals)
• Expense categories mapped to your business reality (not a “misc” bucket)
• Mileage log if you use a vehicle for business
• Home office details if applicable (square footage and how the space is used)
• Payments to contractors and related records (if you issue 1099s)

5) Know the deadlines (and what an extension actually does)

The standard filing deadline is usually in mid-April, but the exact date can shift due to weekends or holidays. If you need more time, an extension can be a smart move—but it’s critical to understand what it changes and what it doesn’t.

• An extension gives you more time to file paperwork.
• It does not automatically give you more time to pay what you owe.
• If you’re self-employed, estimated taxes generally follow a quarterly schedule throughout the year.

6) Final review checklist before you hit “submit”

Errors often come from simple mismatches: a typo in a Social Security number, wrong bank digits, or leaving out a form that was issued. A five-minute review can save weeks of follow-up later.

• Confirm names and SSNs match official records
• Confirm direct deposit routing/account numbers
• Confirm all expected forms are included (W-2s, 1099s, K-1s)
• Confirm your address is current (especially if you moved)
• Save a PDF copy of the filed return and supporting summaries

7) After filing: set up next year to be easier

The best time to prepare for next year’s tax season is right after you file. Save your final PDFs, note what was missing, and set one small habit that reduces stress later. Even a monthly 15-minute bookkeeping check-in can prevent a last-minute scramble.