The Ultimate Tax Document Checklist: Getting Organized for Your 2026 Filing

February 1, 2026 • News, Tax Planning

Tax season is officially here, and if you're like most people in New Haven, you're probably wondering what documents you actually need to file your 2026 return. The good news? Getting organized doesn't have to be stressful.

At Jose's Tax Service, we see hundreds of clients every year, and the ones who have the smoothest experience (and often the biggest refunds) are the ones who show up prepared. So let's walk through exactly what you need to gather before you file.

Start With the Basics: Personal Information

Before you dive into forms and receipts, make sure you have the essentials ready:

Government-issued photo ID (driver's license or passport)
Social Security numbers for yourself, your spouse, and all dependents
Your 2025 tax return (this helps verify your identity with the IRS)
Bank account and routing numbers for direct deposit

Pro tip: If you filed with us last year, we already have most of this information on file, which saves you time when you come in.

Income Documents: What You Need and When to Expect Them

W-2 Forms From Your Employer

Your employer must send you a W-2 by January 31, 2026. This form shows your wages, tips, and taxes withheld. If you changed jobs during 2025, you'll receive a W-2 from each employer you worked for.

Forms 1099: The Catch-All Category

There are several types of 1099 forms, and you might receive multiple depending on your income sources:

1099-NEC: If you did freelance work, consulting, or independent contracting
1099-K: From payment apps like PayPal, Venmo, Cash App, or Etsy (required if you received over $5,000 in payments)
1099-INT: Interest income from banks or savings accounts
1099-DIV: Dividend income from investments
1099-B: If you sold stocks, bonds, or cryptocurrency
1099-G: Unemployment compensation or state tax refunds
1099-R: Pension, IRA, or 401(k) distributions

If you're expecting a 1099 form and haven't received it by mid-February, contact the payer directly.

Self-Employment Income

If you run a side hustle or small business, gather:

Income records from all sources (invoices, sales records, payment app statements)
Expense receipts (supplies, software subscriptions, advertising costs)
Mileage logs if you use your vehicle for business
Records of estimated tax payments you made throughout 2025 (Form 1040-ES)

Deduction Documents: Don't Leave Money on the Table!

Homeownership Records

If you own a home, collect:

Form 1098: Mortgage interest statement from your lender
Property tax bills and receipts
Records of home improvements (these might affect your taxes if you sold your home)

Charitable Contributions

Did you donate to charity in 2025? Keep records of:

Cash donations (bank statements, receipts from organizations)
Non-cash donations like clothing or household items (get a receipt with the organization's name and date)
Mileage driven for volunteer work (14 cents per mile for 2025)

Remember: Donations under $250 don't require a receipt, but you should still keep records. Donations over $250 require written acknowledgment from the charity.

Education Expenses

Gather these if you or your dependents were in school:

Form 1098-T: Tuition statement from colleges or universities
Form 1098-E: Student loan interest paid
Receipts for qualified education expenses (books, supplies, equipment)
Scholarship or fellowship records

Medical Expenses

If you had significant medical costs in 2025, collect:

Health insurance premium statements
Receipts for doctor visits, prescriptions, dental work, and vision care
Mileage to and from medical appointments
Health Savings Account (HSA) or Flexible Spending Account (FSA) contribution records

Keep in mind: Medical expenses are only deductible if they exceed 7.5% of your adjusted gross income.

Childcare Costs

For families paying for daycare or babysitters, you'll need:

Receipts showing amount paid
Provider's name, address, and tax identification number (TIN) or Social Security number
Records for children under age 13

This documentation is required to claim the Child and Dependent Care Credit, which can be worth up to $3,000 for one child or $6,000 for two or more.

Small Business Owners: Your Extended Checklist

If you're self-employed or own a business in New Haven, your document list is longer:

Business Income:

Sales records and invoices
1099 forms received
Credit card processing statements
Payment app transaction reports

Business Expenses:

Office supplies and equipment purchases
Business insurance premiums
Advertising and marketing costs
Professional services (legal, accounting, consulting)
Rent for office or commercial space
Utilities allocated to business use
Vehicle expenses (actual costs or mileage)
Home office measurements and expenses (if applicable)

Asset Information:

Purchase date and cost for equipment, vehicles, or property bought in 2025
Depreciation records for assets from prior years

Documents You Might Not Think About

Cryptocurrency and Digital Assets

If you bought, sold, or traded cryptocurrency in 2025, keep:

Transaction records from exchanges (Coinbase, Binance, etc.)
Dates of purchase and sale
Cost basis information
Records of any cryptocurrency received as payment

Yes, the IRS requires reporting of all digital asset transactions, even if you didn't make money.

State and Local Taxes

Gather records of:

State and local income taxes paid beyond paycheck withholding
Personal property taxes on vehicles or boats
Large purchase receipts (vehicles, boats, major appliances) if claiming sales tax deduction

IRS Correspondence

Have you received any letters or notices from the IRS or Connecticut Department of Revenue Services? Bring those! They're important for addressing any outstanding issues.

How to Stay Organized Year-Round

The best time to get organized for next year's taxes is right now. Here's what I recommend to my clients:

Create a tax folder (physical or digital) and drop documents in as you receive them
Take photos of receipts immediately and store them in a cloud folder
Track mileage using a simple app or notebook
Make quarterly estimated payments if you're self-employed (this prevents a huge bill in April)

What to Do If You're Missing Documents

Don't panic! Here are your options:

Contact the issuer directly to request a duplicate
Check your online accounts (many employers and financial institutions make forms available online)
Request a wage and income transcript from the IRS (this shows what's been reported to them)
Bring whatever you have to Jose's Tax Service: we can help you track down missing documents

Ready to File? We're Here to Help

At Jose's Tax Service, we offer same-day appointments during tax season. Bring your documents, and we'll handle the rest. Our team knows exactly what to look for to maximize your refund and ensure accuracy.

We've been serving New Haven families and small businesses for years, and we understand the unique tax situations you face: from gig economy income to small business deductions to education credits.

Don't wait until April 14th. The earlier you file, the faster you get your refund. Plus, filing early protects you from identity theft and gives us time to address any issues before the deadline.

Give us a call or stop by our office. We'll review your documents, answer your questions, and get your return filed right: guaranteed.

Tax season doesn't have to be overwhelming. With this checklist in hand and Jose's Tax Service by your side, you're ready to tackle 2026 with confidence!