Preparing for the 2026 Tax Season

 

The filing deadline may feel far away, but getting organized early can make tax season much smoother, whether you DIY your return or work with a CPA. Here’s a practical checklist, key dates, and the biggest updates to know as you prepare to file your 2025 return in 2026.

 1) Start with a Simple Document Checklist

Before you open tax software or call your preparer, gather what you’ll need in one place:

Income documents

  • W-2s (wages)
  • 1099-NEC / 1099-MISC (gig work, contractor income)
  • 1099-INT / 1099-DIV (interest & dividends)
  • 1099-B (brokerage sales)
  • 1099-K (payment apps/marketplaces, if you meet the threshold—see below)
  • Any K-1s (partnerships, S-corporations, trusts)

Common deductions & credits support

  • Student loan interest (Form 1098-E)
  • Mortgage interest (Form 1098)
  • Property tax records
  • Charitable donation receipts
  • Childcare expenses and dependent information
  • IRA/HSA contribution records
  • Medical expenses (if you plan to itemize)

Tip: If anything looks off on a W-2 or 1099 (wrong SSN, name, or amounts), request a correction right away; small errors can delay processing.

2) Know the Most Important 2026 Deadlines

Mark these now so they don’t sneak up on you:

  • January 31, 2026: Most W-2s and many 1099s are sent to taxpayers (or the next business day if the 31st falls on a weekend/holiday).
  • April 15, 2026: Deadline to file your 2025 return (or request an extension).
  • April 15, 2026: Deadline for 2025 IRA contributions (even if you file an extension).

3) Big 2025/2026 Updates to Factor In

The Standard Deduction is Higher

For tax year 2025 (filed in 2026), the standard deduction is:

  • $15,750 for single/married filing separately
  • $31,500 for married filing jointly
    (Heads of household are higher than single, too.)

This matters because it can shift the decision of itemizing vs. the standard deduction. If you might itemize, keep clean records for mortgage interest, property taxes, and charitable giving.

Child Tax Credit Increased

The Child Tax Credit is worth up to $2,200 per qualifying child (and the Additional Child Tax Credit may be refundable up to certain limits).

Retirement Contribution Limits Changed for 2026

If you’re planning ahead for retirement savings:

(These are 2026 contribution limits, but they’re useful for planning your paycheck deferrals right now.)

4) Digital Assets: Expect Pore “Paperwork” (and Questions)

If you bought, sold, traded, received, or otherwise disposed of digital assets (crypto, NFTs, etc.), you’ll need to answer the digital asset question on your return, and keep records of transactions.

Also, some taxpayers may receive new reporting forms related to digital asset transactions (depending on activity and brokers).

5) 1099-K Reporting: The Threshold Update to Know

If you use payment apps or sell through online marketplaces, watch for Form 1099-K. The IRS has published guidance that the 1099-K dollar threshold reverts to $20,000 (under updated rules referenced in IRS FAQs/fact sheets).

Even if you don’t receive a 1099-K, income can still be taxable, so it’s smart to track your business/gig income year-round. 

6) Check If You Qualify to File For Free

For the 2026 filing season, IRS Free File offers guided tax software options for taxpayers with AGI of $89,000 or less (in 2025). If you’re above that limit, Free File Fillable Forms may still be available.

7) Life Events Can Change Everything: Make a Quick List

Write down any major changes from 2025 that could affect your taxes:

  • Marriage/divorce
  • Birth/adoption
  • New dependent or change in custody
  • Home purchase/sale
  • Starting a side gig (or closing one)
  • Sale of stock/crypto/property
  • Big changes in income

These are often the reasons returns get delayed, because documents and details are scattered.

8) When in doubt, ask a pro

Tax rules shift, and details matter, especially with self-employment income, itemizing, multi-state moves, dependents, or digital assets. If you’re unsure, it’s worth consulting a qualified tax professional.

This article is for general information only and isn’t tax advice. For guidance tailored to your situation, consult a qualified tax professional.

MBA, MAcc, CPA
Chief Financial Officer and General Manager

Adam Blair

Adam Blair is a certified CPA who began his career with Ernst & Young focusing on Manufacturing, Retail, and Distribution clients. He graduated from Samford University with a Master of Business Administration in Accountancy and successfully passed the Certified Public Accountancy exam. After several years in public accounting, he accepted an opportunity to work for a technology start-up, MedMined, that was later acquired by Cardinal Health. Adam has served several retail businesses as an accountant and business partner in various roles. Today, he serves as the CFO of Main Street, Inc (a parent company of CheckWorks). As the resident financial expert at the company, he believes successful businesses take great care of their customers and focus on building a team of happy employees.

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About Adam Blair

Adam Blair is a certified CPA who began his career with Ernst & Young focusing on Manufacturing, Retail, and Distribution clients. He graduated from Samford University with a Master of Business Administration in Accountancy and successfully passed the Certified Public Accountancy exam. After several years in public accounting, he accepted an opportunity to work for a technology start-up, MedMined, that was later acquired by Cardinal Health. Adam has served several retail businesses as an accountant and business partner in various roles. Today, he serves as the CFO of Main Street, Inc (a parent company of CheckWorks). As the resident financial expert at the company, he believes successful businesses take great care of their customers and focus on building a team of happy employees.