Tax season is officially open in the US. It’s time to gather your tax documents to prepare for your filing! If you don’t have the right paperwork, you could miss out on thousands of dollars in new savings or trigger an audit.
Between the massive changes in the One Big Beautiful Bill Act (OBBBA) and a wave of new digital reporting rules, your “standard” shoebox of receipts might not be enough this time around. In 2026, the IRS is looking for specific proof for new deductions like the $6,000 Senior Bonus and the American-made car loan interest break.
Savings Advice provided the top ten documents to gather, geared to seniors. For current-day workers, add your W2 (s) and 1099 NEC/MISC to this list of ten!
Image by Manfred Steger from Pixabay
1. The SSA-1099 (Social Security Statement)
This is the “old reliable” of senior tax prep. The SSA-1099 shows exactly how much you received in benefits last year and how much federal tax you had withheld. Most of these forms were mailed out in early January, but if yours is missing, you can download a replacement at SSA.gov starting today. In 2026, this form is more critical than ever because it helps determine if the new OBBBA deductions will make your benefits 100% tax-free.
2. Form 1099-R (Retirement Distributions)
If you took money out of an IRA, 401(k), or pension in 2025, you’ll receive a 1099-R for each account. Pay close attention to the “Distribution Code” in Box 7. If you did a Qualified Charitable Distribution (QCD), your form might not explicitly state it, so you’ll need to bring your own records of the transfer to ensure you aren’t taxed on that money.
3. The New Schedule 1-A “Worksheet”
While not a document you receive, you need to prepare a “Modified AGI” worksheet to claim the new $6,000 senior deduction. Because this deduction phases out starting at $75,000 (single) or $150,000 (joint), your accountant will need to see every scrap of income—including tax-exempt interest—to fill out Schedule 1-A correctly.
4. Form 1098-VLI (Vehicle Loan Interest)
Did you buy a new car last year? The OBBBA created a brand-new deduction for interest paid on loans for vehicles assembled in the U.S. For 2026, lenders are issuing Form 1098-VLI to track this. If you haven’t received yours by February 1st, call your lender; this “new” form is easy to overlook, but it can be worth hundreds in tax savings.
5. Form 1099-DA (Digital Assets)
For the first time in 2026, the IRS is requiring brokers to issue Form 1099-DA for cryptocurrency and NFT transactions. If you dabbled in digital assets last year, do not file without this form. Even if you only sold a small amount, the IRS’s new AI systems are specifically looking for “1099-DA mismatches” to trigger audits.
6. Property Tax Statements (The $40,000 SALT Proof)
With the SALT cap jumping from $10,000 to $40,000 in 2026, many seniors who took the standard deduction for years will now find it better to itemize. Bring your physical property tax bills and proof of state income tax paid. This is your ticket to a much larger deduction than you’ve had since 2017.
7. The 2025 “Energy Improvement” Receipts
If you installed a heat pump, new windows, or insulation last year, 2026 is the last “big” year for the Energy Efficient Home Improvement Credit. You need the specific manufacturer’s certification and your final paid invoice. Without these details, you can’t claim the up to $3,200 credit that helps offset the high cost of home modernization.
8. Medical Expense Summary (The 7.5% Threshold)
With healthcare costs and Medicare premiums rising, more seniors are crossing the 7.5% AGI threshold for medical deductions. Gather your receipts for anything Medicare didn’t cover: dental work, hearing aids, eyeglasses, and even the “facility fees” we’ve been warning you about. In 2026, these “small” bills can add up to a massive tax shield.
9. Form 1095-A (Health Insurance Marketplace)
If you aren’t yet on Medicare and bought insurance through the Exchange, you must have Form 1095-A. This form is used to reconcile your Premium Tax Credits. With the OBBBA’s changes to healthcare subsidies, failing to include this form is the #1 reason 2026 tax returns are being rejected by the IRS.
10. Charitable Contribution Receipts (Even if you don’t itemize!)
In 2026, the “Standard Charitable Deduction” is back. Even if you don’t itemize, you can deduct up to $1,000 (single) or $2,000 (joint) for cash donations. You must have a written acknowledgment from the charity for any gift over $250. Don’t leave this money on the table just because you aren’t filling out a full Schedule A.
Details Matter
A word of advice: details matter when filing your taxes. It’s a good idea to have all tax-related documents to submit your filing to avoid questions and/or audits down the line.
For those who have read my Sunday morning posts for a while, you know how I focus on details frequently. It is sadly a reality that in most areas of life, details make a big difference.
Keeping up with the details in life isn’t easy, I know. And keeping up to protect everyone and everything you’ve accumulated can be overwhelming. Let me know if I may be of assistance to you. Pop me a note via Email or check out what I offer @ The Living Planner.
If you prefer a Zoom connect, Book a Time with Lynn for a complimentary 30-minute Zoom with me. If you’re one who likes to pre-plan, my book is a resource for you. The 2026 edition of Living Planner What to Prepare Now While You Are Living © is ready! Check it out HERE.
Quote of the week: “How you do anything is how you do everything” is widely attributed to author and Zen student Cheri Huber.
Gather your documents – it’s time! Lynn
#Can’tPredictCanPrepare #CareForPeopleCareForBusiness