Why Social Security Can Create a Tax Problem You Never Saw Coming

By David Hughes | Financial Advisor, Resurgent Financial Advisors

Retirement is supposed to feel like a release.

The meetings stop. The calendar softens. The work inbox loses its grip on your mood. For many people, Social Security feels like the first truly dependable paycheck of retirement life. It arrives with a sense of permanence. It feels earned. It feels, frankly, a little sacred.

Then tax season rolls around and suddenly retirement doesn’t feel quite so simple.

A lot of retirees are surprised to learn that Social Security benefits can become taxable depending on how much other income shows up alongside them. That surprise isn’t just common. It’s understandable. Social Security often feels separate from the rest of the tax conversation, almost like it should sit in its own protected lane. The IRS doesn’t see it that way. The tax code looks at the broader income picture, and that’s where the friction often starts.

This is where retirement can get a little sneaky. The issue usually isn’t one giant mistake. It’s more often a series of perfectly reasonable income decisions that begin interacting in ways people never expected. A pension check starts. An IRA withdrawal fills a cash need. A few dividends show up. Maybe there’s some tax-exempt interest. None of those things look dramatic on their own. Together, they can make more of Social Security taxable than a retiree ever saw coming.

Can Social Security Benefits Really Be Taxed?

Yes, they can. The Social Security Administration says some people who receive Social Security have to pay federal income tax on part of their benefits, and that up to 85% of benefits may become taxable depending on filing status and total income. SSA also notes that if you file as an individual and total income exceeds $25,000, or file jointly and total income exceeds $32,000, part of your benefits may be taxable.

That phrase, “up to 85%,” tends to rattle people. It sounds dramatic, and it often gets misunderstood. It does not mean the government taxes Social Security at an 85% rate. It means up to 85% of the benefit may be included in taxable income. Those are two very different things. One sounds like a financial horror movie. The other is a tax calculation, annoying though it may still be.

That distinction matters. A retiree who hears “85% taxable” may assume most of the check is disappearing. What it really means is that a portion of the benefit may be included in the income figure the IRS uses to calculate tax. The actual tax owed depends on the rest of the household’s return.

How Does The IRS Decide Whether Social Security Is Taxable?

The IRS and SSA use a formula often referred to as combined income. SSA explains that combined income includes adjusted gross income, nontaxable interest, and half of Social Security benefits. IRS Publication 915 uses the same framework for determining how much of a benefit may be taxable.

That’s where the surprise begins.

A lot of people look at retirement income one source at a time. Social Security feels manageable. Pension income feels manageable. An IRA withdrawal for a trip, a car, or a home project feels manageable. The formula, though, isn’t looking at one source in isolation. It’s looking at how the entire mix behaves once it lands on the same return.

Retirement income often arrives in layers, not all at once. That’s part of why this catches thoughtful people off guard. Nobody has to be reckless for a tax issue to appear. A household can be doing everything in a calm, measured, perfectly sensible way and still end up with more taxable Social Security than expected.

What Income Can Make Social Security More Taxable?

This is the part that tends to get people leaning forward in their chairs.

Traditional IRA withdrawals can matter. Pension income can matter. Part-time wages can matter. Interest income can matter. Ordinary dividends and capital gain distributions can matter. Even tax-exempt interest can matter for this specific calculation. IRS Publication 915 specifically includes taxable income items and tax-exempt interest in the formula used to determine whether Social Security becomes taxable.

That last one feels especially rude. Many people hear “tax-exempt” and assume it disappears from the tax conversation entirely. Not here. Municipal bond interest may be exempt from federal income tax, but it still gets pulled into combined income for purposes of determining whether Social Security becomes taxable.

There’s a strange little lesson hiding inside that rule: conservative income choices aren’t invisible. They still have tax consequences, just sometimes in places people don’t expect.

Why Do Ira Withdrawals Create So Much Tax Friction In Retirement?

Traditional IRA money usually hasn’t been taxed yet, which is part of what made it attractive during working years. IRS guidance says amounts in a traditional IRA generally aren’t taxed until distribution, which means withdrawals often increase taxable income in the year they’re taken.

That’s perfectly manageable in a vacuum. The trouble starts when those withdrawals show up next to Social Security.

A retiree may decide to pull a little more from an IRA for a kitchen update, a family trip, or simply a more comfortable lifestyle. Nothing about that choice is inherently reckless. Still, that extra withdrawal may do two things at once. It may increase taxable income directly, and it may also cause more of Social Security to become taxable under the combined-income rules.

That’s where people start using phrases like “Why does this feel worse than I expected?” The answer is that retirement income doesn’t always behave in straight lines. One income decision can create a ripple effect in another part of the return. It’s not always intuitive, and it’s rarely obvious from a bank balance alone.

Do Pensions Make Social Security Taxable Too?

They can. Pension and annuity payments may be fully taxable if there is no after-tax basis in the contract, or partly taxable if after-tax dollars were contributed. IRS guidance on pensions and annuities explains that tax treatment depends on the source of the contributions and the structure of the benefit.

That means a retiree with a pension and Social Security may already be closer to the threshold than expected. Add IRA withdrawals, investment income, or even a little consulting income, and the picture can shift quickly.

This is one reason retirement taxes can feel so oddly personal. The income sources that were supposed to create security can start stepping on each other’s toes. Nobody loves seeing a carefully built retirement plan turn into an accidental tax puzzle. Still, that’s often what happens when the moving parts haven’t been viewed together.

What Are The Social Security Tax Thresholds Retirees Should Know?

Current IRS and SSA guidance uses two threshold levels for many taxpayers. For single filers, combined income above $25,000 can make part of Social Security taxable, and combined income above $34,000 can make up to 85% taxable. For married couples filing jointly, those thresholds are $32,000 and $44,000. IRS Publication 915 and SSA retirement-benefit materials both reflect those levels.

Those numbers are familiar to planners for one reason: they haven’t moved with inflation. That means more retirees can run into them over time even if their lifestyle doesn’t look extravagant.

That’s part of what makes the experience feel so unfair to many households. The retiree may not feel wealthy. The tax formula doesn’t particularly care how retirement feels. It cares how the income stacks.

Does More Income Always Mean A Better Outcome In Retirement?

In broad terms, more income is still better than less income. Nobody should read this and conclude that earning, withdrawing, or receiving income is somehow a mistake. The real issue is tax friction, not the existence of income itself.

A lot of retirees expect retirement income to behave like a faucet. Turn it on, use what’s needed, pay the obvious tax, and move on. In reality, retirement income often behaves more like a set of gears. Turn one, and another starts moving.

That’s why “more income” can sometimes feel less rewarding than expected in the short term. A larger IRA withdrawal may increase cash flow, though it may also increase taxable Social Security. A pension may offer welcome stability, though it may narrow future tax flexibility. Those aren’t arguments against income. They’re reminders that coordination matters.

How Can Retirees Avoid A Social Security Tax Surprise?

The first win is awareness. A tax surprise is often more frustrating than a tax bill itself. Once retirees understand that Social Security, IRA withdrawals, pensions, and investment income can interact, the conversation shifts from confusion to planning.

The Social Security Administration allows beneficiaries to request voluntary federal tax withholding from benefits, and the IRS uses Form W-4P for periodic pension and certain IRA payments and Form W-4R for many nonperiodic retirement payments. The IRS also states that the default withholding rate for many nonperiodic payments covered by Form W-4R is 10%.

That doesn’t erase the tax issue. It can, however, reduce the feeling that the IRS showed up uninvited and started rearranging the furniture.

Retirees may also benefit from looking at income sources together instead of one at a time. A withdrawal that seems harmless in June can look very different by April once Social Security, pensions, investment income, and other distributions are all reflected on the return. A little coordination can go a long way toward reducing friction.

What’s The Real Lesson Here?

Social Security isn’t the villain in this story. Taxes aren’t new. Retirement income isn’t broken. The real problem is that many people enter retirement expecting a simpler tax life and instead discover a more interconnected one.

That can feel discouraging at first. It can also be manageable once the rules are understood.

A retiree doesn’t need a perfect tax return to have a good retirement. What helps most is knowing that one source of income may affect another, and that “safe” or familiar income can still create tax consequences. Social Security may look like a standalone benefit, though in practice it often behaves like part of a larger tax ecosystem.

That’s the part many people never see coming.

This article is for general educational purposes only and isn’t individualized tax, legal, or investment advice. Readers should consult qualified tax and financial professionals regarding their specific circumstances.

Michael Perros

Founder, Encompass Financial Advisors

G. Michael Perros is the founder of Encompass Financial Advisors. Mr. Perros has served as a financial advisor and branch manager of a leading financial services organization since 1982. His leadership has been demonstrated in a variety of significant decision-making roles over his career.

Mike is a 1981 graduate of the University of Kentucky, with a double major in agriculture and a minor in agriculture economics. Mike is a graduate of the Securities Industry Institute, a three-year program held at the Wharton School on the campus of the University of Pennsylvania and offered to only a limited number of attendees each year. Furthermore, he served on the Board of Trustees of the Securities Industry Institute from 1999 to 2006. This board appointment provided quality executive education to professionals in the securities industry. Only those individuals who exemplify the true desire to better others while fully understanding the many aspects of the industry are chosen.

Continuing education is a theme throughout Mr. Perros' career. Mike also completed a complex six-month curriculum accredited by the Estate and Wealth Strategies Institute of Michigan State University. The advanced courses covered financial planning, estate planning, risk management, and other wealth management strategies. In December 2002, he became an Accredited Investment Fiduciary™ (AIF®), a qualification offered through the Center for Fiduciary Studies at the University of Pittsburgh KATZ Graduate School of Business.

Mike has an extensive background in community and civic service. He is past president of the local Red Cross Chapter, past president of the Boyle County UK Alumni Association, past member of the National UK Alumni Association Board of Directors, past president of the Heart of Danville Main Street Program, past president of the Danville-Boyle County Chamber of Commerce, and past president of the Danville Schools Educational Foundation. Mike was instrumental in founding the Lottie Ellis Foundation, a charitable trust that benefits a variety of individuals and organizations in Boyle County, Kentucky.

Mike has continued in service to his fraternity, Delta Tau Delta. Immediately on graduation from UK in 1981, Mike worked full time as a chapter consultant. His national focus, involving visits to more than 40 chapters in a single year, led to a perspective that serves him well even today. He has served as division vice president, covering Kentucky and Tennessee, and has served on special task forces as appointed. Mike currently serves as president of the Delta Epsilon House Corporation of Delta Tau Delta where he co-chaired a successful $2.2 million campaign, leading to the renovation of that chapter house at the University of Kentucky. He was inducted into the UK Greek Hall of Fame in 2003 and the Distinguished Service Chapter of Delta Tau Delta, a body of 400 inductees from the fraternity's 150,000 members throughout its history, in 2006.

Mike is a proud father of three daughters, Haley, Michaelle, and Tess. They reside in Danville, Kentucky.

Stuart Canzeri

Managing Partner, Peachtree Financial Group

With over two decades of experience, Stuart Canzeri has been helping their clients achieve the financial freedom to live an abundant life. As an Independent Registered Investment Advisor, Stuart works exclusively for his clients – not for a financial corporation. Stuart is married with two sons and is active in his church.

Matt Pohlman

East Franklin Capital

Matt has been providing financial advice to clients for almost 20 years, helping families and businesses manage wealth and assets to meet their long term financial goals. And, while he may have less hair, Matt continues to advise clients in much the same way as he did when he started: with transparency, integrity and discipline.

Before founding East Franklin Capital (formerly Pohlman Capital Advisors), Matt worked as a wealth advisor at GenSpring Family Offices, where he was responsible for advising high net worth clients on a variety of investment and planning matters. Matt was the founding advisor in the GenSpring Chapel Hill office.

Prior to his time with GenSpring Family Offices, Matt managed the Family Office for Franklin Street Partners and held the position of Director of Client Services. Matt served on the Management Committee at Franklin Street Partners. During his time at both Franklin Street Partners and GenSpring Family Offices, Matt worked with families, guiding and advising them through significant investment and financial decisions focused at all times on the goals and objectives each client set out to achieve. Before his start in the investment advisory world, Matt helped companies put their financial house in order. Now, he works with family and businesses to pursue their goals and provide peace of mind.

Matt has been a North Carolina CPA since 2003 and received a Master’s in Accounting from the University of North Carolina at Chapel Hill, where he was a Harris Scholar, and a BSBA from the University of North Carolina at Chapel Hill.

Lee Caffey

Finance Associate, Peachtree Financial Group

Lee is a finance professional with a strong analytical background and a passion for helping individuals navigate financial decisions. He specializes in financial analysis, strategy, and resource development. With a focus on clarity and accuracy, he works to simplify complex financial concepts and provide valuable insights to clients.

Rebecca Bowling

Resurgent Financial Advisors

With nearly a decade of experience in the financial industry, Rebecca is a dedicated investment adviser who is passionate about helping clients build a secure financial future. After passing the licensing exam in 2023, Rebecca has combined years of industry knowledge with a deep understanding of client needs, offering personalized advice and comprehensive strategies to meet diverse financial goals.

Before transitioning into finance in 2015, Rebecca spent 15 years working in corporate business in Atlanta, gaining valuable experience in management and strategic planning. This background in business and corporate operations provides Rebecca with a unique perspective on the financial needs of individuals and businesses alike. Whether helping clients plan for retirement, optimize investments, or navigate complex financial decisions, Rebecca is dedicated to providing thoughtful, effective solutions.

Outside of work, Rebecca enjoys spending quality time with family. Married for 20 years and the proud parent of an 11-year-old daughter, Rebecca is actively involved in their daughter's dance and volleyball competitions. When not cheering on her athletic pursuits, Rebecca enjoys reading and traveling, always seeking new opportunities for learning and personal growth.

With a commitment to both professional excellence and family values, Rebecca is excited to partner with clients to achieve long-term financial success and peace of mind.

David Hughes

Resurgent Financial Advisors

David's unique mastery of tax and equity compensation is tightly integrated with his reality-based financial planning background. With over 16 years of experience, he developed his skillsets connecting people's use of capital with what is important to them. He is passionate about helping people make informed decisions by understanding the trade-offs implicit in life's decisions.

Our process begins with getting to know you and your goals. Tell us where you want to go, and we'll work with you to develop a plan that suits your needs. And as your life changes, we'll adjust your plan so it better aligns with your new path.

We believe a detailed planning process can be one of the most effective ways to create financial security. An effective plan may not only provide financial security throughout your life, it can reduce the damage disability, critical illness, or other sudden losses of income may have.

Callan Bush

Marketing Associate, East Franklin Capital

As the Marketing and Branch Operations Manager at East Franklin Capital, Callan complements Matt’s leadership by bringing a fresh perspective to the firm’s strategic marketing and client services. With a Public Health degree from the University of North Carolina Wilmington and a passion for financial wellness, Callan connects clients with East Franklin Capital’s personalized financial planning services and ensures that operations run smoothly.

While Matt focuses on guiding families and businesses through complex wealth management strategies, Callan works to amplify that mission by fostering lasting client relationships and building the firm’s presence in the community. Together, they are dedicated to helping clients achieve long-term financial security and success, with Callan’s attention to detail and emphasis on clear communication ensuring a seamless experience at every step.

Anna Lee

Marketing Associate, Peachtree Financial Planning

Anna is a marketing professional passionate about storytelling through media and design. With a degree in Advertising, Anna specializes in creating impactful campaigns, media strategies, and digital content. With a focus on enhancing consumer experiences, she simplifies complex topics through engaging, brand-aligned materials.

Dawn Patterson

Director, Peachtree Financial Planning

With over 15 years of experience, Dawn is a seasoned Relationship Manager in the Private Wealth Management industry.

Known for her exceptional expertise and unwavering dedication, Dawn has consistently delivered outstanding results throughout her career.

As a Relationship Manager within Peachtree Financial Group, Dawn continues to thrive, leveraging her wealth of knowledge and experience to help clients navigate the complexities of their financial lives.

Blane Brooks

Vice President, Business Development

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Sarah Sutton

Chief Compliance Officer

Sarah joined Resurgent in October 2021, leading Resurgent's compliance team. In her role, she is responsible for implementation, oversight, and monitoring of compliance programs.

Sarah comes to Resurgent via Oster Consulting. She has over 25 years of experience in the financial services industry on the revenue, operations and compliance sides of the business. Her expertise includes compliance supervision, leading firm and regulatory examinations, regional and retail branch management, brokerage and clearing operations, developing and implementing advisor best practices along with technology training, financial planning delivery and implementation, advisor and firm transition management to new firms and channels, and project management for advisor and client solutions.

Prior to joining Oyster Consulting, Sarah served as Director of Investment Services at First Horizon Advisors, Inc., where she led the Wealth Services division that handled all brokerage operations and advisor support, including managing all branch activity.

Sarah and her husband live in North Mississippi with their four boys. She enjoys cooking challenging recipes and spending time with family. Over the years she’s been a board member for a range of non-profit organizations serving her local community in Tennessee.

Katherine K. Decker

Chief Financial Officer
Kathy Decker manages financial accounting and reporting for Resurgent. In addition, she oversees the human resources and benefits functions. Kathy was previously Vice President and Treasurer of Cox Enterprises, a leading media, communications and automotive services company.

In that role, she managed Cox's capital structure and funding needs across the globe. She oversaw the company's capital raising activities, including bank financing, bond and asset-backed securities issuance, and treasury operations, as well as Patriot Act compliance.

Previously, Kathy served in other positions within Cox Enterprises, including Group Vice President of Manheim Financial Services and Manheim's Director of Treasury Operations. Before joining Cox, she held a number of positions in corporate and investment banking at First Union National Bank and Wachovia Bank. Kathy hold a B.B.A. degree from Auburn University and has the Certified Treasury Professional designation.
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Kip R. Caffey

Chief Executive Officer

Kip Caffey is responsible for crafting and executing Resurgent Advisors' strategy. He has been in the financial services industry for over 35 years.

He began his career in the Corporate Finance Department at J. C. Bradford & Co., eventually becoming a managing director and a partner in the firm.

Subsequently, he was Senior Managing Director at SunTrust Robinson Humphrey and its predecessor, The Robinson-Humphrey Company, where he was co-head of the Corporate Finance Department.

Prior to forming Resurgent, Kip was a partner in Cary Street Partners, serving as its chief executive from 2009 to 2015.

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