Here We Go Again: What to Gather Before You File

As tax season approaches, many people feel a familiar mix of uncertainty and dread, wondering whether they missed something or if an unexpected tax bill awaits. Even during my time working at the IRS, I felt that same tension as April drew near. The best antidote to the anxiety that I’ve found is preparation. Taking a thoughtful, organized approach can replace anxiety with confidence. While the following list isn’t exhaustive, it’s designed to help you get into the right mindset and make the filing process smoother and more predictable.

Employment Forms

W-2 and the various 1099s that you receive are matched by the IRS against forms submitted by employers and payers. Missing or mismatched information can trigger delays of refunds or notices.

1. W-2: Your employer is required to provide you with a W-2 form, which is typically mailed to you by the end of January.
2. 1099s: If you are a contractor or self-employed, you will receive 1099 forms with information on how much you were paid last year. You should expect to receive your 1099s by early February. 1099-MISC, which accounts for rents, royalties and other income, generally arrives by late January to early February. Investment related 1099s (1099-DIV/INT./B) often arrive mid to late February.

If you do not receive your 1099s from your clients or W-2 from your employer, reach out in February to make sure you receive a copy before you file your taxes.

Last Year’s Taxes: Both Federal and State

A copy of last year’s state and federal return can help you understand what deductions you utilized last year and can help you fill out your tax return for this year. By reviewing the prior year’s tax forms, you can maintain consistency, spot carryforwards and avoid overlooking items. 

Documentation for Any Deductions

Each year, many file using the standard deduction, which is a set amount that taxpayers can automatically subtract from their income without the hassle of itemizing. However, itemizing may reduce your taxes more if your deductible expenses exceed the standard deduction threshold. Key categories include:

1. Charitable Donations: Gather any receipts, invoices from your charitable donations or acknowledgement letters. For non-cash gifts always keep receipts, a Form 8283 is required for total non-cash contributions over $500 and you may need a qualified appraisal for items over $5,000.
2. Medical Bills: If your eligible unreimbursed medical expenses are more than 7.5% of your adjusted gross income, you may be eligible to deduct your qualified unreimbursed medical care expenses. 
3. Retirement Account Contributions (Form 5498 and Form 5498-SA): You should receive Form 5498 from the bank or brokerage that holds your account in January. You do not need your file 5498 to file, but track contributions made on your statements to be able to provide your tax preparer with the most current information.  For HSA contributions, you’ll receive a 5498-SA and a 1099-SA for distributions.
4. Mortgage Interest (Form 1098): For homeowners, Form 1098 details the amount of interest you paid on your mortgage during the year. 
5. State and Local Taxes (SALT): The SALT deduction cap has increased under the One Big Beautiful Bill to $40,000, with a phaseout for households above $500,000. Keep property tax receipts and year-end state tax statements.
6. Student Loan Interest (Form 1098-E): If you paid over $600 in student loan interests, you should receive a copy of your 1098-E for use in your tax filing.

Documentation for Any Credits You May Be Eligible for

Tax credits allow taxpayers to reduce the income on which they owe taxes. Gather the right forms to substantiate eligibility. Some popular credits include:

1. Child Tax Credit (Letter 6419): Letter 6419 includes the amount of advanced Child Tax Credit payments someone has received so they can claim any remaining credit on their tax return. 
2. Tuition Credit (Form 1098-T): Colleges and other post-secondary institutions will send Form 1098-T, which outlines any “qualified educational expenses” paid in the last year, including tuition, enrollment materials, etc. 
3. American Opportunity Credit and Lifetime Learning Credit (Form 8863): This form helps you claim credits on qualified education expenses paid to an eligible postsecondary educational institution. 
4. Child and Dependent Care Credit (Form 2441): Collect the provider’s name, address, TIN/EIN and amounts paid for eligible care that enabled you to work or look for work. 

Tax Documents for Your Banking and Wealth Accounts

To ensure a seamless tax filing process, it is crucial to gather all your tax documents for both your bank and wealth accounts, regardless of whether you receive them via mail or through our online banking and wealth portals.

1. Consolidated 1099 Package (Brokerage): Typically includes 1099‑DIV, 1099‑INT, 1099‑B, and 1099‑OID. Many custodians issue these in mid‑ to late‑February and may send corrected forms in March.
2. Retirement Distributions (Form 1099‑R): Covers IRA, pension, and plan distributions, rollovers, Roth conversions and QCDs (qualified charitable distributions from IRAs).
3. Partnerships, S‑Corps, Trusts (Schedule K‑1): Often arrive later (March into spring/summer). If you expect K‑1s, inform your CPA early, you may need to file an extension.
4. Bank Interest (Form 1099‑INT) and Dividends (Form 1099‑DIV): Don’t overlook separate forms from banks, credit unions and individual issuers outside your main brokerage.

If you have any questions or need assistance regarding access to your tax documents, we encourage you to reach out to your dedicated banker or wealth advisor. They possess the expertise and knowledge to provide you with the necessary guidance and support, ensuring that you have all the information you need for a successful tax filing.

Timing, Logistics and Smart Process

To ensure a smooth filing experience, it’s helpful to establish a clear process for organizing, reviewing and securely storing your tax documents.

1. Centralize Access: Download PDFs from payroll, bank, brokerage and benefits portals and store them in a single, secure folder.
2. Name and SSN Checks: Ensure your name, SSN and address are consistent across forms, a small discrepancy can cause IRS mismatches.
3. Funding Deadlines: IRA and HSA contributions for the prior tax year can generally be made up to the filing deadline (Tax Day).
4. Extensions vs. Payments: An extension extends time to file, not to pay. If you extend, make a reasonable payment by the deadline to reduce interest and penalties.
5. Security: Use encrypted channels or your advisor’s secure portal to share documents.

Meet With Your Advisor

Now is a great time to meet with your advisor to review your personal financial situation and make sure your finances, assets and goals are still in alignment. While meeting with your advisor, you can discuss your current situation and if there is anything that you should be aware of or doing to maximize tax savings. Some topics you might discuss with your advisor at tax time might be about eligibility and the potential benefits of a Roth IRA conversion, how you’re managing capital gains and about the tax efficiency of your asset allocation.

Connect with your advisor if you have any questions as you prepare your taxes. We’re happy to help so you have a productive — and potentially money-saving — experience.