Retire With Ryan
7 Tax Mistakes to Avoid When Filing Your 2025 Taxes, Ep#296
Retire With Ryan
•March 10, 2026•22 min
0
Retire With Ryan•Mar 10, 2026
Why It Matters
Tax errors can trigger penalties, delayed refunds, or unnecessary tax liability, directly impacting retirees’ financial security. With the 2025 One Big Beautiful Bill Act introducing new deductions and higher SALT caps, staying informed is crucial to maximize savings and avoid costly oversights.
Key Takeaways
- •File by deadline; extensions don’t waive tax payment.
- •Verify all personal data, bank info, and all 1099s.
- •Double‑check calculations; use CPA or software to avoid errors.
- •Claim 2025 deductions: higher SALT cap, vehicle interest.
- •Report IRA/HSA contributions and pay quarterly estimated taxes.
Pulse Analysis
Tax season arrives each April, and the most basic error—missing the filing deadline—still costs millions. The IRS treats late filers as non‑filers, applying interest and penalties that compound the amount owed. While extensions grant extra time to submit paperwork, they do not postpone the payment of any balance due. Taxpayers who wait for a refund also delay receiving it, reducing cash flow. Prompt filing, even with an extension for paperwork, protects against unnecessary charges and keeps refunds on schedule.
Accuracy on the return is equally critical. Simple oversights—misspelled names, wrong Social Security numbers, or outdated bank routing—can stall processing and misdirect refunds. More subtle gaps, such as omitted W‑2s, 1099s, or unreported 401(k) rollovers, often trigger audits or unexpected tax liabilities. Double‑checking calculations with a CPA or reputable software eliminates arithmetic errors that could overpay or underpay. The 2025 tax code also introduces new opportunities: a higher SALT cap, expanded vehicle‑interest deductions, and increased standard deductions for seniors. Claiming these provisions requires up‑to‑date knowledge, making professional guidance valuable.
Finally, many filers overlook retirement and health savings contributions that reduce taxable income. Deductible IRA deposits and HSA funding, including catch‑up amounts for those over 55, must be reported even when made after the calendar year. Missing these entries forfeits valuable deductions. Self‑employed retirees and business owners also risk penalties by neglecting quarterly estimated tax payments. The IRS safe‑harbor rule—100 % of prior‑year liability or 110 % for high earners—offers a buffer, but only if withholding or estimated payments meet the threshold. Consulting a tax professional ensures all credits, deductions, and payment schedules are optimized.
Episode Description
Tax season is here, and if you're just now gathering your documents to file your return—or preparing them for your CPA—this is the time to slow down and make sure you're not making costly mistakes. In this episode, I walk through seven tax mistakes I frequently see both tax preparers and self-filers make when filing their returns. Some of these errors seem simple on the surface, but they can lead to penalties, missed deductions, delayed refunds, or paying more taxes than necessary. My goal in this episode is to help you avoid these pitfalls so you can file confidently and keep more of your money where it belongs.
You will want to hear this episode if you are interested in…
[00:00] Why tax season mistakes are more common than you might think
[01:00] The costly consequences of filing after the tax deadline
[02:30] Why double-checking basic personal information matters more than you think
[03:30] The hidden risk of missing 1099 forms in the digital age
[04:15] How a rollover mistake can accidentally create taxable income
[05:00] The surprisingly common issue of unsigned tax returns
[05:30] Why simple math errors can lead to penalties or unexpected refunds
[06:30] When free tax preparation help may—or may not—be a good option
The Most Common Tax Filing Errors
Many tax mistakes don't happen because people are careless. They happen because people rush, assume something was already handled, or simply overlook a small detail that turns into a big issue later. One of the most common problems I see is filing past the tax deadline. Each year millions of taxpayers fail to file by the April deadline, which can trigger penalties and interest if taxes are owed. Even if you're due a refund, filing late can delay getting your money back.
Another major issue is incomplete or incorrect information on the return. Something as simple as entering the wrong bank account for a direct deposit or forgetting to include a tax document can delay processing or create unnecessary headaches. And in today's digital world, many tax forms are delivered electronically, which means it's easier than ever to overlook a 1099 if you forget about an account.
Missing Deductions and Overlooking Opportunities
Beyond basic filing errors, many taxpayers lose money by missing deductions or not understanding new tax rules. Starting with the 2025 tax return, several changes introduced under the "One Big Beautiful Bill Act" create additional tax breaks. These include adjustments to the standard deduction, expanded deductions for certain taxpayers, and other potential opportunities many filers may not even realize exist.
I also discuss why deciding between the standard deduction and itemizing can significantly affect how much tax you owe. In recent years, higher standard deductions meant fewer people itemized their taxes. But changes to the state and local tax deduction cap may reopen the door for some taxpayers to itemize again, especially homeowners with mortgages or individuals paying higher state and local taxes.
Understanding what qualifies as an itemized deduction—from mortgage interest to medical expenses and charitable contributions—can make a meaningful difference in your tax outcome.
Retirement Contributions and Quarterly Tax Pitfalls
Two other mistakes I see regularly involve retirement and tax planning details that often get overlooked. Some taxpayers make IRA or Health Savings Account contributions but forget to report them properly on their return. That mistake can cause them to miss legitimate deductions that could reduce their taxable income.
Another issue is failing to pay quarterly estimated taxes. This commonly affects self-employed individuals, business owners, and retirees who receive income without automatic tax withholding. Without proper withholding or estimated payments, taxpayers may face penalties—even if they eventually pay the full amount owed.
The good news is that many tax mistakes can be corrected. If you discover an issue after filing, an amended return can often resolve the problem. But catching these issues before filing is always the best strategy.
Resources Mentioned
Fidelity HSA
RetireWithRyan.com/podcast/296
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Show Notes
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