Tax season officially runs from late January through April 15 (or April 18 this year since the 15th falls on a holiday). Most Americans wait until the last two weeks and scramble. Do not be most Americans. A little bit of organization now saves hours of stress later and, more importantly, ensures you do not miss deductions that reduce what you owe. This checklist covers every document you need, every deadline that matters, and the decisions you need to make before you file.
Documents to gather first: W-2s from every employer you worked for (these must be mailed to you by January 31). 1099-NEC or 1099-MISC if you did freelance or gig work over $600. 1099-INT for bank interest over $10. 1099-DIV for investment dividends. 1099-B for investment sales. 1099-G if you received unemployment benefits. 1098 for mortgage interest paid. 1098-T for college tuition. 1098-E for student loan interest. 1095-A if you had Marketplace health insurance. SSA-1099 if you received Social Security benefits. Keep all of these in one folder -- physical or digital.
Key decisions before you file: Standard deduction or itemize? For 2025 taxes (filed in 2026), the standard deduction is $15,000 for single filers and $30,000 for married filing jointly. You should only itemize if your deductible expenses (mortgage interest, state and local taxes up to $10,000, charitable donations, medical expenses over 7.5% of AGI) exceed the standard deduction. For most people, the standard deduction is larger. Second decision: filing status. Married couples should run the numbers both ways (jointly and separately) -- filing jointly is usually better, but separately can save money if one spouse has large medical expenses or student loan payments.
Deductions and credits most people miss: The Earned Income Tax Credit (EITC) is the most under-claimed credit in the tax code. A family of four earning under $63,000 could receive up to $7,830. Single filers under $18,500 with no children can still receive up to $632. The Saver's Credit gives 10-50% of retirement contributions back as a tax credit for individuals earning under $38,250 (single) or $76,500 (married filing jointly). Student loan interest is deductible up to $2,500 even if you take the standard deduction. And if you moved for a military assignment, moving expenses are still deductible for active duty service members.
Filing options from cheapest to most expensive: IRS Free File (completely free if AGI is under $84,000 -- use IRS.gov/FreeFile). Volunteer Income Tax Assistance (VITA) offers free in-person filing for people earning under $67,000, people with disabilities, and people with limited English proficiency. Cash App Taxes is completely free for all filers with no income restrictions. TurboTax, H&R Block, and TaxAct charge $0-200+ depending on complexity. A CPA or enrolled agent typically charges $200-500 for individual returns but is worth it if you have self-employment income, rental properties, investment sales, or other complex situations.
Critical deadlines: January 31 is when employers must send W-2s and companies must send most 1099s. April 15 (or April 18 if the 15th falls on a weekend/holiday) is the filing deadline. If you cannot file by the deadline, file Form 4868 for a six-month extension -- this extends the filing deadline but NOT the payment deadline. You must still estimate and pay any taxes owed by April 15 to avoid penalties. If you are owed a refund, file as early as possible. The IRS typically issues refunds within 21 days of e-filing. If you file a paper return, expect 6-8 weeks. Choose direct deposit for the fastest refund delivery.
