{"id":1518,"date":"2026-03-10T14:09:00","date_gmt":"2026-03-10T22:09:00","guid":{"rendered":"http:\/\/www.checkworks.com\/blog\/?p=1518"},"modified":"2026-03-16T10:21:57","modified_gmt":"2026-03-16T18:21:57","slug":"preparing-for-the-tax-season","status":"publish","type":"post","link":"https:\/\/blog.checkworks.com\/index.php\/preparing-for-the-tax-season\/","title":{"rendered":"Preparing for the 2026 Tax Season"},"content":{"rendered":"<div class=\"order-details-big__content\">\n<div class=\"tab-content\">\n<div id=\"tab_original_text\" class=\"tab-pane active\">\n<div class=\"tab-pane-content\">\n<div class=\"slim-scroll-tab tab-content\">\n<div id=\"preview_originaltext\" class=\"tab-pane html-preview-tab-content active\">\n<div class=\"no-scroll\">\u00a0<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<\/div>\n<p><span style=\"font-weight: 400\">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\u2019s a practical checklist, key dates, and the biggest updates to know as you prepare to file your 2025 return in 2026.<\/span><\/p>\n<p><!--more--><\/p>\n<h2><span style=\"font-weight: 400\">\u00a0<\/span><span style=\"font-weight: 400\">1) Start with a Simple Document Checklist<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Before you open tax software or call your preparer, gather what you\u2019ll need in one place:<\/span><\/p>\n<p><b>Income documents<\/b><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">W-2s (wages)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">1099-NEC \/ 1099-MISC (gig work, contractor income)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">1099-INT \/ 1099-DIV (interest &amp; dividends)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">1099-B (brokerage sales)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">1099-K (payment apps\/marketplaces, if you meet the threshold\u2014see below)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Any K-1s (partnerships, S-corporations, trusts)<\/span><\/li>\n<\/ul>\n<p><b>Common deductions &amp; credits support<\/b><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Student loan interest (Form 1098-E)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Mortgage interest (Form 1098)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Property tax records<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Charitable donation receipts<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Childcare expenses and dependent information<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">IRA\/HSA contribution records<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Medical expenses (if you plan to itemize)<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400\">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.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">2) Know the Most Important 2026 Deadlines<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Mark these now so they don\u2019t sneak up on you:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400\"><b>January 31, 2026:<\/b><span style=\"font-weight: 400\"> Most W-2s and many 1099s are sent to taxpayers (or the next business day if the 31st falls on a weekend\/holiday).<\/span><\/li>\n<li style=\"font-weight: 400\"><b>April 15, 2026:<\/b><span style=\"font-weight: 400\"> Deadline to file your 2025 return (or request an extension).<\/span><\/li>\n<li style=\"font-weight: 400\"><b>April 15, 2026:<\/b><span style=\"font-weight: 400\"> Deadline for 2025 IRA contributions (even if you file an extension).<\/span><\/li>\n<\/ul>\n<h2><span style=\"font-weight: 400\">3) Big 2025\/2026 Updates to Factor In<\/span><\/h2>\n<h3><span style=\"font-weight: 400\">The Standard Deduction is Higher<\/span><\/h3>\n<p><span style=\"font-weight: 400\">For tax year 2025 (filed in 2026), the <\/span><a href=\"https:\/\/www.nerdwallet.com\/taxes\/learn\/standard-deduction\"><span style=\"font-weight: 400\">standard deduction<\/span><\/a><span style=\"font-weight: 400\"> is:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">$15,750 for single\/married filing separately<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">$31,500 for married filing jointly<\/span><span style=\"font-weight: 400\"><br \/><\/span><span style=\"font-weight: 400\">(Heads of household are higher than single, too.)<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400\">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.<\/span><\/p>\n<h3><span style=\"font-weight: 400\">Child Tax Credit Increased<\/span><\/h3>\n<p><a href=\"https:\/\/www.irs.gov\/credits-deductions\/individuals\/child-tax-credit?\"><span style=\"font-weight: 400\">The Child Tax Credit <\/span><\/a><span style=\"font-weight: 400\">is worth up to $2,200 per qualifying child (and the Additional Child Tax Credit may be refundable up to certain limits).<\/span><\/p>\n<h3><span style=\"font-weight: 400\">Retirement Contribution Limits Changed for 2026<\/span><\/h3>\n<p><span style=\"font-weight: 400\">If you\u2019re planning ahead for retirement savings:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">401(k) elective deferral limit is $24,500 for 2026<\/span><\/li>\n<li style=\"font-weight: 400\"><a href=\"https:\/\/www.irs.gov\/newsroom\/401k-limit-increases-to-24500-for-2026-ira-limit-increases-to-7500\"><span style=\"font-weight: 400\">Catch-up contributions generally increase to $8,000 for age 50+<\/span><\/a><span style=\"font-weight: 400\"> (with a higher catch-up that can apply for ages 60\u201363)<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400\">(These are 2026 contribution limits, but they\u2019re useful for planning your paycheck deferrals right now.)<\/span><\/p>\n<h2><span style=\"font-weight: 400\">4) Digital Assets: Expect Pore \u201cPaperwork\u201d (and Questions)<\/span><\/h2>\n<p><span style=\"font-weight: 400\">If you bought, sold, traded, received, or otherwise disposed of digital assets (crypto, NFTs, etc.), you\u2019ll need to answer the <\/span><a href=\"https:\/\/www.irs.gov\/newsroom\/reminders-for-taxpayers-about-digital-assets?\"><span style=\"font-weight: 400\">digital asset question<\/span><\/a><span style=\"font-weight: 400\"> on your return, and keep records of transactions.<\/span><\/p>\n<p><span style=\"font-weight: 400\">Also, some taxpayers may receive new reporting forms related to digital asset transactions (depending on activity and brokers).<\/span><\/p>\n<h2><span style=\"font-weight: 400\">5) 1099-K Reporting: The Threshold Update to Know<\/span><\/h2>\n<p><span style=\"font-weight: 400\">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 <\/span><a href=\"https:\/\/www.irs.gov\/newsroom\/irs-issues-faqs-on-form-1099-k-threshold-under-the-one-big-beautiful-bill-dollar-limit-reverts-to-20000?\"><span style=\"font-weight: 400\">referenced in IRS FAQs\/fact sheets<\/span><\/a><span style=\"font-weight: 400\">).<\/span><\/p>\n<p><span style=\"font-weight: 400\">Even if you don\u2019t receive a 1099-K, income can still be taxable, so it\u2019s smart to track your business\/gig income year-round.\u00a0<\/span><\/p>\n<h2><span style=\"font-weight: 400\">6) Check If You Qualify to File For Free<\/span><\/h2>\n<p><span style=\"font-weight: 400\">For the 2026 filing season, IRS Free File offers guided tax software options for taxpayers with <\/span><a href=\"https:\/\/www.irs.gov\/newsroom\/use-irs-free-file-to-conveniently-file-your-return-at-no-cost\"><span style=\"font-weight: 400\">AGI of $89,000 or less<\/span><\/a><span style=\"font-weight: 400\"> (in 2025).\u00a0<\/span><span style=\"font-weight: 400\">If you\u2019re above that limit, <\/span><a href=\"https:\/\/www.irs.gov\/filing\/irs-free-file-do-your-taxes-for-free\"><span style=\"font-weight: 400\">Free File Fillable Forms<\/span><\/a><span style=\"font-weight: 400\"> may still be available.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">7) Life Events Can Change Everything: Make a Quick List<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Write down any major changes from 2025 that could affect your taxes:<\/span><\/p>\n<ul>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Marriage\/divorce<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Birth\/adoption<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">New dependent or change in custody<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Home purchase\/sale<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Starting a side gig (or closing one)<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Sale of stock\/crypto\/property<\/span><\/li>\n<li style=\"font-weight: 400\"><span style=\"font-weight: 400\">Big changes in income<\/span><\/li>\n<\/ul>\n<p><span style=\"font-weight: 400\">These are often the reasons returns get delayed, because documents and details are scattered.<\/span><\/p>\n<h2><span style=\"font-weight: 400\">8) When in doubt, ask a pro<\/span><\/h2>\n<p><span style=\"font-weight: 400\">Tax rules shift, and details matter, especially with self-employment income, itemizing, multi-state moves, dependents, or digital assets. If you\u2019re unsure, it\u2019s worth consulting a qualified tax professional.<\/span><\/p>\n<p><i><span style=\"font-weight: 400\">This article is for general information only and isn\u2019t tax advice. For guidance tailored to your situation, consult a qualified tax professional.<\/span><\/i><\/p>\n\n\n<hr class=\"wp-block-separator has-alpha-channel-opacity\" \/>\n\n\n<div style=\"font-style:normal;font-weight:400;\" class=\"has-text-align-left has-link-color has-text-color has-black-color has-background has-white-background-color wp-block-post-author has-small-font-size wp-elements-635a1be63b0cdc1ff12cc149825cbb9e\"><div class=\"wp-block-post-author__avatar\"><img alt='' src='https:\/\/secure.gravatar.com\/avatar\/2e902f3a86e5b2e37909190b9dfc01bc?s=96&#038;d=mm&#038;r=g' srcset='https:\/\/secure.gravatar.com\/avatar\/2e902f3a86e5b2e37909190b9dfc01bc?s=192&#038;d=mm&#038;r=g 2x' class='avatar avatar-96 photo' height='96' width='96' \/><\/div><div class=\"wp-block-post-author__content\"><p class=\"wp-block-post-author__byline\"><strong>MBA, MAcc, CPA<\/strong><br><strong>Chief Financial Officer and General Manager<\/strong><\/p><p class=\"wp-block-post-author__name\"><a href=\"https:\/\/blog.checkworks.com\/index.php\/author\/adam-blair\/\" target=\"_self\">Adam Blair<\/a><\/p><p class=\"wp-block-post-author__bio\">Adam Blair is a certified CPA who began his career with Ernst &amp; 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.\r\n\r\nAdam 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.<\/p><\/div><\/div>","protected":false},"excerpt":{"rendered":"<p>\u00a0 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\u2019s a practical checklist, key dates, and the biggest updates to know as you prepare to file your 2025 return in 2026.<\/p>\n","protected":false},"author":15,"featured_media":2568,"comment_status":"open","ping_status":"open","sticky":false,"template":"","format":"standard","meta":{"footnotes":""},"categories":[81,30,33],"tags":[37,102,93,32,100,101,34],"aioseo_notices":[],"_links":{"self":[{"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/posts\/1518"}],"collection":[{"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/posts"}],"about":[{"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/types\/post"}],"author":[{"embeddable":true,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/users\/15"}],"replies":[{"embeddable":true,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/comments?post=1518"}],"version-history":[{"count":7,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/posts\/1518\/revisions"}],"predecessor-version":[{"id":2696,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/posts\/1518\/revisions\/2696"}],"wp:featuredmedia":[{"embeddable":true,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/media\/2568"}],"wp:attachment":[{"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/media?parent=1518"}],"wp:term":[{"taxonomy":"category","embeddable":true,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/categories?post=1518"},{"taxonomy":"post_tag","embeddable":true,"href":"https:\/\/blog.checkworks.com\/index.php\/wp-json\/wp\/v2\/tags?post=1518"}],"curies":[{"name":"wp","href":"https:\/\/api.w.org\/{rel}","templated":true}]}}