Your Tax Season Checklist: Everything to Gather Before You File

Tax season has a way of sneaking up on people. One day it's January, and the next it's mid-March and you're scrambling to track down a 1099 from a brokerage account you almost forgot you had.

The good news is that a little organization upfront makes the whole process significantly smoother — for you, your CPA, and your overall peace of mind. Whether you're filing yourself or working with a tax professional, having everything in one place before you start saves time, reduces errors, and ensures you don't miss anything that could cost you money.

Here's everything you need to gather before you file.

Key Deadlines to Know

Before diving into documents, keep these dates on your radar:

• February 2 — Employers must send W-2s; most 1099s are due to recipients
• February 17 — Deadline for certain 1099s (brokerage accounts, dividends)
• March 16 — Deadline for S-corp and partnership returns (Form 1120-S and 1065)
• April 15 — Individual federal tax return deadline (Form 1040)
• April 15 — Deadline to contribute to an IRA for the prior tax year
• October 15 — Extended individual return deadline (if extension filed by April 15)

If you're working with a CPA, ask them when they need your documents — many firms have internal deadlines well before April 15 to manage their workload.

Personal Information

Start with the basics. Your tax preparer needs this for every return:

• Social Security numbers for you, your spouse, and any dependents
• Date of birth for all filers and dependents
• Bank account and routing number for direct deposit of any refund
• Last year's tax return (useful for reference and carryover items)
• Identity Protection PIN (IP PIN) if you've been issued one by the IRS

Income Documents

This is the heart of your return. Gather every document that reflects income received during the year.

From employment:

• W-2 from each employer

From self-employment or business ownership:

• 1099-NEC (nonemployee compensation)
• 1099-K (payment card or third-party network transactions)
• Business income and expense records
• Mileage logs if claiming vehicle deductions
• Home office documentation if applicable

From investments and retirement accounts:

• 1099-B (proceeds from broker transactions — stock sales)
• 1099-DIV (dividends and distributions)
• 1099-INT (interest income)
• 1099-R (distributions from IRAs, pensions, annuities)
• SSA-1099 (Social Security benefits)
• K-1 forms (income from partnerships, S-corps, trusts, or estates)

From other sources:

• 1099-G (unemployment compensation or state tax refunds)
• Rental income records and related expenses
• Alimony received (for agreements prior to 2019)
• Gambling winnings (W-2G)
• Any other income received during the year

Retirement Account Activity

If you made contributions to or took distributions from any retirement account, document all of it:

• Traditional IRA, Roth IRA, or SEP-IRA contribution amounts and dates
• 401(k) or 403(b) contribution records (usually shown on your W-2)
• Required Minimum Distribution amounts taken
• Qualified Charitable Distribution records (QCD acknowledgment letters from charities)
• Roth conversion records if applicable
• Form 5498 (IRA contribution information — usually arrives in May, after filing, but useful for records)

Deduction and Credit Documentation

This is where many people leave money on the table. Gather documentation for every potential deduction.

Homeownership:

• Form 1098 (mortgage interest statement)
• Property tax records
• Points paid on a new mortgage or refinance
• Energy efficiency improvement receipts (windows, insulation, heat pumps, solar)

Charitable giving:

• Written acknowledgment for any single gift of $250 or more
• Bank records or receipts for smaller cash donations
• Records of non-cash donations (clothing, household items) with estimated values
• Mileage driven for volunteer work
• Records of any Qualified Charitable Distributions made from your IRA

Medical expenses:

• Total out-of-pocket medical and dental expenses (deductible to the extent they exceed 7.5% of AGI)
• Long-term care insurance premiums
• Health Savings Account (HSA) contributions and distributions (Form 1099-SA and Form 5498-SA)

Education:

• 1098-T (tuition statement)
• 1098-E (student loan interest)
• 529 plan contribution and distribution records

Business and self-employment:

• All business expense receipts and records
• Home office measurements and expenses
• Health insurance premiums paid (deductible for self-employed)
• Self-employed retirement plan contributions (SEP-IRA, Solo 401k, SIMPLE IRA)
• Estimated tax payments made during the year (Form 1040-ES vouchers or bank records)

State and Local Tax Information

• Amount of state and local income taxes paid during the year
• State tax refund received last year (may be taxable if you itemized)
• Vehicle registration fees (deductible in some states)
• Records of sales tax paid on major purchases if electing the sales tax deduction

Life Events That Affect Your Return

If any of the following happened in the prior year, make sure your tax preparer knows:

• Marriage or divorce
• Birth or adoption of a child
• Death of a spouse or dependent
• Purchase or sale of a home
• Sale of a business or significant assets
• Retirement or start of Social Security benefits
• Inheritance received
• Moving to a new state

These events can significantly change your tax situation — and missing them can mean missing deductions or credits you're entitled to.

A Note for Retirees

If you're retired, a few items deserve special attention:

• Confirm your RMD was taken in full — the penalty for a missed RMD is significant
• Gather documentation for any QCDs made directly to charity from your IRA
• Review your Medicare premium notices — IRMAA surcharges based on income are worth discussing with your advisor
• Check whether your Social Security benefit is being correctly withheld (or whether you need to adjust voluntary withholding)

A Note for Business Owners

Business owners often have the most complex returns — and the most opportunity. Make sure you have:

• Complete profit and loss records for the year
• Payroll records and year-end summaries
• Depreciation schedules for assets
• Records of any equipment purchased (Section 179 deduction)
• Documentation for any retirement plan contributions made for yourself and employees
• Records of estimated tax payments made quarterly

If you're not working with a CPA who specializes in small business, tax season is a good time to evaluate whether you should be.

Get Organized Once, Benefit All Year

The best tax seasons are the ones where nothing is a surprise. That means keeping records throughout the year — not scrambling in April to reconstruct what happened in January.

A simple folder system — physical or digital — organized by category works well for most people. Every time a tax-related document arrives, it goes in the folder. By the time filing season comes around, the work is already done.

And if you're not sure whether something belongs in your return, the answer is almost always: bring it anyway and let your CPA decide. It's far better to have too much than to miss something that matters.

Ready to Make This Your Most Organized Tax Season Yet?

At Sage Street Wealth, we review tax returns as part of our planning process — not just to check a box, but to find opportunities that inform the year ahead. If you'd like to have that conversation, we'd love to connect.

See if Sage Street is the right fit for you →