Missed Tax Deductions? How to Review Your 2025 Tax Return for Overtime, Tips, and Car Loan Interest (OBBBA Guide)

Why You Should Double-Check Your 2025 Tax Return

Unlike me, you probably filed your taxes weeks ago. You know, that thing you do where you take a weekend and go all Adam Scott *severance* at your computer. Now, I’m going to ask you to try to *reintegrate* with that moment and review that return for accuracy. Whether you delegate to a CPA or file your own taxes, it’s highly possible you left money on the table. Provisions of the One Big Beautiful Bill Act (OBBBA) in 2025 might have led you to overlook certain tax deductions that differ from those in previous years. If you received overtime pay, tips, or bought a new vehicle in 2025, you could have qualified for certain savings. In addition to the legislative changes made in the middle of last year, we’ll also provide some of the more common (and easily fixable) tax mistakes we see each year. 

OBBBA Tax Changes That May Not Be Automatic

This is not an exhaustive list of tax-related changes enacted by last year’s legislation. Some of those changes will automatically flow through your return. For instance, the senior bonus deduction. Individuals age 65 or older can deduct an additional $6,000 of income, and married couples age 65 or older can deduct an additional $12,000 of income from their federal taxable income if their modified adjusted gross income is less than $75,000 for individuals or $150,000 for joint filers. Because it’s age-based, tax-filing software will catch this automatically, assuming you list that correctly. 

However, there are three (3) new tax deductions that your tax-filing software may NOT catch automatically and may require additional information or documentation.

  • Overtime Pay Deduction 

  • Tip Deduction

  • Car Loan Interest Deduction

Overtime Pay Deduction: What to Know

If you receive compensation for overtime hours, most commonly “time and a half”, you are likely eligible for the overtime pay deduction unless your household income is too high, as noted below. 

Overview

  • Effective for Tax Years 2025 – 2028
  • Maximum Annual Deduction
    • Individuals: $12,500
    • Married Filing Jointly: $25,000
  • Income Phaseout
    • Individuals: $150,000
    • Married Filing Jointly: $300,000

Eligibility

  • Employees with a Social Security number who are covered by the Fair Labor Standards Act and considered overtime-eligible (non-exempt). 

Employer Reporting Requirements

Because of the mid-year legislative changes, employers are NOT required to itemize overtime compensation on employee W-2s for 2025. However, this is a requirement for tax years 2026 – 2028. If your employer added this to your 2025 Form W-2, it would be listed in Box 14. However, there’s no need to fret if you know you worked eligible overtime and Box 14 is blank. You can refer back to your last pay stub of the calendar year, which will provide you with your Year-To-Date (YTD) total overtime compensation for 2025. 

Claiming the Overtime Pay Deduction

The most important note about claiming the overtime pay deduction is that only the overtime premium is tax-deductible, not the full amount. 

Example: Jon is an individual filer with less than $150,000 of modified adjusted gross income. His normal hourly rate of pay is $30. His overtime premium is “time and a half”, and he receives $45/hr as compensation. He worked 250 hours of overtime in 2025, for a total overtime compensation of $11,250. To calculate how much he can deduct from his federal taxable income, Jon can either take his overtime premium of $15 ($45 – 30) and multiply it by the number of hours worked, or divide the total compensation of $11,250 by 3. Either way, the result is that Jon can now deduct $3,750 of his overtime pay against his 2025 federal income. Suppose Jon can deduct that amount against income in the 22% marginal tax bracket, that would save him approximately $825 in federal taxes. 

To see if the overtime pay deduction made it onto your tax return, taxpayers can refer to page 2 of their Form 1040, Line 13b. And more specifically, they should look directly at Schedule 1-A, Part III, labeled “No Tax on Overtime.” Box 14 will ask you to list your qualified overtime compensation.

So, using the example above, Jon would list $3,750 in Box 14a. This would flow through to boxes 14c and 21.

Tip Deduction: What to Know

Overview

  • Effective for Tax Years 2025 – 2028
  • Maximum Annual Deduction
    • Individuals or Married Filing Jointly: $25,000
  • Income Phaseout
    • Individuals: $150,000
    • Married Filing Jointly: $300,000

Eligibility

  • See the IRS-compiled list of occupations that are eligible because they “customarily and regularly receive tips.”
  • Tips must be voluntary and in cash or charged to a credit or debit card. They include your share of any pooled tips. One notable exception is that mandatory service charges are NOT considered qualified tips for this deduction. 

Employer Reporting Requirements

  • For employees, your employer is supposed to record your income from tips on your Form W-2, and this should be itemized in either Box 7 or 14. 
  • For independent contractors, your 1099 will likely not show tips separately. 

Note that reporting requirements are a two-way street. Employees are required to maintain a daily record of cash and noncash tips and submit them to their employer monthly when the total exceeds $20 for that month. If employers allocate tips to employees in Box 8 of their Form W-2, it’s the employees’ responsibility to maintain records proving they received less income and do not owe taxes on the full amount. For self-employed individuals and 1099 independent contractors, you also have a responsibility to maintain daily records of tip income received, even though this income is not reported to the business where services are rendered. Any tips not reported by your employer on your W-2 must be reported on Form 4137 when you file. In 2026, this will be required to qualify for deducting those tip amounts. 

Claiming the Tip Deduction

To see if the tip deduction made it onto your tax return, taxpayers can refer to page 2 of their Form 1040, Line 13b. And more specifically, they should look directly at Schedule 1-A, Part II, labeled “No Tax on Tips.”

Car Loan Interest Deduction: What to Know

Overview

  • Effective for Tax Years 2025 – 2028
  • Maximum Annual Deduction
    • Individuals or Married Filing Jointly: $10,000
  • Income Phaseout
    • Individuals: $100,000
    • Married Filing Jointly: $200,000

Eligibility

  • Qualified vehicle purchased with a loan originated after December 31, 2024
  • Must have undergone final assembly in the United States, as verified by the National Traffic Highway Safety Administration
  • Vehicle must be for personal use with the taxpayer as the original purchaser

Claiming the Car Loan Interest Deduction

Taxpayers must include the VIN number. You do not need to itemize your deductions to claim the car loan interest deduction. 

To see if the tip deduction made it onto your tax return, taxpayers can refer to page 2 of their Form 1040, Line 13b. And more specifically, they should look directly at Schedule 1-A, Part IV, labeled “No Tax on Car Loan Interest.” 

Example: Stevie and David are joint filers with an adjusted gross income below $200,000. They purchased a qualified vehicle in 2025 for $50,000 and financed $40,000 at 5%. They paid $5,291 in annual interest. Assuming a 22% marginal tax rate, deducting this interest from their adjusted gross income would save them $1,164 in federal taxes owed.

Other Common Tax Return Errors

The remaining common errors are unrelated to the OBBBA legislation but occur all too often. These aren’t just warnings for taxpayers who file their own taxes. Remember, your CPA may not automatically identify some of these issues, as their work relies on receiving accurate documentation.

Missing Mortgage Interest (Multiple 1098s)

This is a big one for taxpayers who itemize their deductions. Each year, you’ll receive a Form 1098: Mortgage Interest Statement from your lender detailing the amount of interest you paid. But what if your lender changes mid-year because your loan was sold? You’ll now receive two (2) Form 1098s, one from your previous lender and one from your current lender. You have to submit or upload both forms to deduct the full amount of mortgage interest paid that year from all lenders, as that number does not carry over to each form! 

Medical Expense Deduction

Another deduction that households that itemize can miss is in years with large healthcare expenses. Different than the self-employed healthcare deduction, taxpayers can deduct eligible expenses that exceed 7.5% of their gross income for the year. This is common in years when you have surgical procedures, undergo IVF treatments, or give birth. These expenses don’t live on any issued tax form, so you have to manually enter them or let your tax professional know.

Filing Duplicate 1099s

If you have a non-qualified brokerage account with a custodian such as Charles Schwab, Fidelity, or Vanguard, you’ll likely receive a 1099 by the end of February detailing any capital gains, dividends, and interest for the year. However, sometimes your custodian receives additional information from the fund companies that requires them to *correct* your 1099. They will then issue you a separate, corrected version of the 1099 in March. Do not upload both to your tax return! Doing so will ultimately double your tax liability as you’ll find yourself paying on duplicate information. 

Misreporting Cost Basis of Restricted Stock Units (RSUs)

Upon receiving RSUs, you’ll likely have the compensation added to your ordinary income for the year on your Form W-2. However, the custodian (the investment company that facilitates your RSUs) will provide you with a tax form called a 1099-B that shows whether you sold any of your stock. The cost basis on this document will likely read $0, which is incorrect. Your custodian will also send you a document called a “Supplemental Information Sheet,” which will list the correct cost basis information for your RSUs. This sheet allows you to properly report it on your tax return and avoid any potential double taxation. 

Backdoor Roth Mistakes

Mechanically, this topic deserves its own post on how to correctly make a nondeductible Traditional IRA contribution and convert it to a Roth IRA. The outputs of Form 8606, which documents this transaction, are rather simple. But for taxpayers who file their own taxes using DIY software, we see recording errors more often than not. Furthermore, making contributions and doing conversions across different tax and/or calendar years introduces an additional layer of complexity. 

Excess Health Savings Account (HSA) Contributions

This isn’t a tax prep error, but rather a coordination error among spouses. When both spouses are taking advantage of their HSAs through their respective workplaces, it can lead to contributions that exceed the household IRS limit. For two (2) reasons, the first being that the combined individual limits are MORE than the household limit. The second being, if one spouse has dependents on their High-Deductible Health Plan, they may already be making the full family contribution. So any contribution (employee or employer) that is added to the spouse’s plan will also exceed the IRS household contribution limit. If you do not catch or correct this, you’ll pay a 6% excise tax year-over-year as long as the overcontributed amount remains in the account or isn’t applied to a future year contribution limit.

Filing an Amended Return

If you missed a deduction, you can file an amended return within three years to correct it and get a refund. While these are some common errors we’ve seen on client tax returns, please note this is not an exhaustive list. Always consult with your tax professional before making decisions related to your personal situation.

For helpful tools when it comes to tax planning and filing, check out the Free Resources page on our website. 

Currently working? Here’s a separate, helpful guide for reviewing your 2025 tax return.

Frequently Asked Questions About Missed Tax Deductions

Q1: How do I know if I missed a tax deduction on my 2025 return?
A1: Check Form 1040, Line 13b and review Schedule 1-A for specific deductions like overtime pay, tips, and car loan interest. Compare your return against your income documents (W-2, 1099s, loan statements) to confirm nothing was overlooked. 
Q2: Can I deduct overtime pay on my taxes in 2025? 
A2: Yes, but only the overtime premium portion (the extra pay above your standard rate) is deductible. The deduction is subject to income limits and must be calculated manually in many cases. 
Q3: Are tips tax-deductible in 2025? 
A3: Qualified tips may be deductible if they are voluntary and properly reported. However, service charges do not qualify, and you must maintain accurate records to claim the deduction. 
Q4: Is car loan interest deductible for personal vehicles? 
A4: Under 2025 rules, yes—if the vehicle meets eligibility requirements, including U.S. final assembly and a qualifying loan. You do not need to itemize deductions to claim it. 
Q5: Can I fix a mistake after filing my taxes? 
A5: Yes. You can file an amended return (Form 1040-X) to correct errors or claim missed deductions, typically within three years of the original filing date.
Fiduciary, fee-only, Certified Financial Planner, Mike Turi

Mike Turi, CFP® APMA™ is the Founder and a Lead Financial Planner at Upbeat Wealth, a fee-only firm based in New Orleans and serving clients virtually across the country. He specializes in providing straightforward financial guidance to ambitious young families as they navigate life’s many milestones.

Do you have questions about what we shared in this post, or anything else in general? Feel free to schedule a free consultation or drop us a line!

Sign up for our newsletter (at the bottom of this page) to stay up to speed on our Upbeat Insight.

Disclaimer: All content in this article is provided for educational, general information, and illustration purposes only. None of the information is intended as investment, tax, accounting, or legal advice. Nor is it a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult with a financial planner, accountant, and/or legal professional for advice on your specific situation. Read our full disclaimer here.

Traditional vs Roth 401(k): How to Choose the Right Contribution Strategy

The Simple Framework for 401(k) Contributions

Not to sandbag our version of this question right out of the gate, but this blog/article/education exists on every personal finance resource on the interwebs. Yet, it’s still one of the most common questions that people standing around at a bar, looking for free financial advice clients ask us. 

The math is really quite simple. If you’re in a lower tax bracket when making withdrawals in retirement, you’d want to make Pre-Tax Contributions now. If your funds are subject to a higher tax rate later, you’d be thankful you made Roth contributions now. But that’s where the simplicity ends. You might not even know what you’re having for dinner, let alone what life might look like in 40 years. And even if you had that crystal ball, there’s no telling what federal and state tax rates might be. If you’re an actual wizard and do know what the tax brackets will be, there are still scenarios where having access to both Traditional (Pre-Tax) and Roth buckets would be beneficial. 

And I won’t bury the lede any further: Here’s a simple way to view the timing of Traditional and Roth contributions. 

  • Early Career: Roth 

  • Mid Career: 50/50 Split

  • Peak Earning Years: Traditional

But if you want some additional guidance on the full considerations between the two, keep reading!
Because, as mentioned, you are probably somewhat uncertain about:

  • Retirement Age
  • Reduced Income Prior to Retirement (Back to School, Sabbatical) 
  • State of Residence
  • Expected Federal Tax Brackets
  • If You’ll Need a Large Sum of Money Suddenly (Home, Health, Grandkid’s Education)
  • Tax Brackets for Your Kids Upon Inheriting Money
  • If You’ll Inherit Money and If That Will Be Pre-Tax or Roth
  • Needing Health Insurance Before Medicare-eligibility

Explain 401(k) Contributions To Me Like I’m Five

401(k) plans are employer-sponsored retirement accounts that enable employees to contribute through automatic payroll deductions. You might hear a 401(k) called a “Traditional 401(k)” or a “Roth 401(k),” but they are the same employer-sponsored plan. It’s a single 401(k) that accepts two different contribution types. Also, “Traditional” Contributions refer to Pre-Tax Contributions, and these terms can be used interchangeably. Some 401(k) plans even offer a third type of 401(k) contribution known as After-Tax Contributions, which should not be confused with Roth contributions. We’ll skip the After-Tax Contribution bucket for the purposes of this blog.

Understanding How 401(k) Contributions Are Taxed

The key difference between Traditional and Roth contributions is the timing of taxation.

  • Traditional 401(k) Contributions: Defer tax now, pay taxes later

  • Roth 401(k) Contributions: Pay tax now, withdraw tax-free later

A popular metaphor is “the seed vs. the harvest.” The seed is taxed when you make Roth Contributions. The harvest is taxed when you make Traditional or Pre-Tax Contributions. Mathematically, if you’re subject to the same tax rate on contributions and withdrawals, it doesn’t matter whether you’re taxed today (the seed) or in the future (the harvest). 

An example:

When the tax rate is flat, the math – maths. Even though you paid more in cumulative taxes by deferring them, your net distribution remains unchanged.

Won’t My Tax Rate Always Be Lower In Retirement?

“I’m not making any money, so why would I be paying more in taxes?” right? RIGHT!? It certainly makes sense, but it’s not that straightforward. Here are some reasons you might end up subject to a higher tax rate or face higher costs later on, even without any earnings. 

Future Federal Marginal Tax Rates and Brackets

When it comes to future tax rates, we are purely speculating. Here is a chart of the historical highest and lowest marginal tax rates since its inception. 

And this chart doesn’t even fully capture how difficult it is to predict how future rates may move across different income levels. The highest marginal rate may apply to only a small number of taxpayers. More specifically, it will come down to how each income threshold is taxed at what rate and where you will fall in comparison. However, if you were to speculate that our low maximum marginal tax rate, combined with increasing national debt, might result in higher future tax rates, I certainly wouldn’t stop you! But note that’s been a popular thesis for decades, and current tax rates have actually decreased relative to certain periods.  

State Tax Rates

The next biggest reason your tax rate may increase is a change in your state of residence. See how your state or desired home in retirement stacks up!

Thinking about retiring in California after working in Louisiana? That’s a big jump in state taxes paid on distributions. Therefore, you might think twice about making traditional contributions today, since you’ll pay a good bit extra at the state level later. But then you might hit your 50s, and your entire personality could be honoring the late, great Jimmy Buffett. So now you’re riding motorcycles and drinking pina coladas (not at the same time, of course!) and eyeing a move to Florida. Well, then you might be kicking yourself a little for not saving pre-tax in Louisiana, since Florida has no income tax. 

Obscure Taxes, Penalties, and Costs

Based on current tax rules, there are additional financial *consequences* such as the Net Investment Income Tax (NIIT), the Medicare Income-Related Monthly Adjustment Amount (IRMAA), and how health insurance premiums are determined if you go through the Healthcare.gov exchange without access to an employer-sponsored plan or Medicare and have too much income to qualify for Medicaid. Being forced to make a large amount of pre-tax distributions within a calendar year could result in additional money owed, even if it’s not directly tied to the tax rate on the retirement income itself. 

Required Minimum Distributions (RMDs)

Some people are naturally great savers. And if you’re great at saving, you might have a hard time spending money, too. Therefore, you may build a substantial pre-tax nest egg. Based on your birthdate, the government says you must start taking withdrawals from this money between the ages of 70.5 and 75. These mandatory Required Minimum Distributions could exceed what you were earning while working. 

You Inherit Money, or Your Kids Inherit Your Money

If you are around my age or most of our clients’ ages, you have boomer parents. And if you have boomer parents, you know they just don’t talk about money. It’s not in their DNA. You’ll get what you get when you get it. But if you are fortunate enough to get *something* and it’s pre-tax money, you’ll have ten (10) years to empty the account to $0. It’s a GOOD problem to have, but it still affects how much you get to keep. There’s a lot of tax planning involved. And if your money is already tied up in 100% pre-tax accounts and the government is forcing you to take distributions, you might find yourself with very little flexibility on what tax rate it’s subject to. You’ll just owe what you owe. 

Or, if you are the one saving now and building a 100% pre-tax allocation with the goal of passing money to your own kids, they might actually be fulfilling the American dream of doing better than you! And now you have deferred taxes on money your kids will realize at a higher rate. 

That’s A Lot of *Stuff*

That’s not even an all-encompassing list. But it’s worth listing some of the main reasons it’s never as simple as anyone wants to make it. A lot of these things, we just don’t know. And that’s okay! A financial planner can certainly help you address some of these blind spots and make educated guesses/assumptions around tax planning. But if you’re doing it yourself, I’d suggest focusing on what seems best now rather than overthinking every future multiverse scenario. 

Emotional Benefits of Roth vs Traditional Contributions

Traditional (Pre-Tax) Contributions Provide CONTROL

I’ll start with pre-tax contributions because I just spent the last couple of minutes of your time making you second-guess whether you should even make pre-tax contributions at all. While we’ll give further financial guidance on when you should consider making pre-tax contributions later in this article, here’s a softer reason. For the most part, you maintain control over your tax consequences. By deferring taxes now, you have control over when you make distributions based on your tax rate at that time. While the government tries to force your hand with RMDs, that may be decades away. 

But aren’t there rules and penalties that prevent you from making distributions before Age 59.5? Yes, but you could do what’s known as Roth Conversions. As the name suggests, Roth Conversions allow you to convert Pre-Tax funds to Roth funds beforehand and avoid the 10% early withdrawal penalty. There are a few other considerations and *gotchas* that I won’t go into here, but you should definitely look into them if you’re considering making Roth Conversions. Here’s an educational piece from Schwab that outlines them. I mention Roth Conversions because they are a great tax-planning tool for those who are going back to school, taking a sabbatical, on track for early retirement, or have an opportunity to fill lower tax-rate thresholds before RMDs.

Roth Contributions Provide Peace of Mind

While you lose control over how your money is taxed, the good news is you don’t have to worry about it anymore! Assuming certain holding periods and age thresholds are met, the money in this bucket is 100% unequivocally yours! Taxes have already been paid at the time of contribution, and distributions are not included in your gross income. Therefore, you don’t have to worry about obscure tax laws or rules that tax you more, reduce certain credits, or penalize you as your Adjusted Gross Income or Modified Adjusted Gross Income increases.

Even if you don’t end up with the highest tax-adjusted balance, understanding how much money truly belongs to you can make retirement planning easier.

How Life Events Can Influence Contribution Strategy

There isn’t a better graphic to illustrate this than the one in this Kitces.com article, which I’ve included below.

Above, you’ll see reasons you may contribute to a Traditional IRA, split contributions 50/50, or contribute to a Roth IRA, based on life events that affect your tax rate. Here’s the synopsis:

Contributions by Tax Rate

  • 12% or Lower: Roth Contributions

  • 22% – 24%: 50/50 Split

  • 32%+: Pre-Tax Contributions

While the future is important, it’s often more practical to concentrate on today’s events and adjust accordingly. As your life changes, so should your 401(k) contribution method. This approach helps you systematically build your allocations across different tax buckets, offering you maximum control and flexibility when taking distributions before retirement, during retirement, or passing on an inheritance to your family. 

Ultimately, a balanced approach to your 401(k) contributions will help you make the most of your funds as you near or enter retirement.

Frequently Asked Questions About 401(k) Contributions

Q1: Should I choose Roth or Traditional 401(k) contributions?
Choose Roth contributions if you expect your tax rate to be higher in retirement. Choose Traditional contributions if you expect your tax rate to be lower later. Many investors benefit from using both to create tax flexibility.
Q2: Is it better to pay taxes now or in retirement?
It depends on your future tax bracket. Paying taxes now (Roth) is better if tax rates rise or your income increases later. Deferring taxes (Traditional) is better if you expect lower income in retirement.
Q3: Can I make both Roth and Traditional 401(k) contributions?
Yes. Most employer plans allow you to split contributions between both types, helping create tax diversification for retirement withdrawals.
Q4: Why should I have both Roth and Traditional retirement savings?
Having both creates flexibility. You can withdraw from different accounts strategically to manage taxes, avoid Medicare premium increases, and reduce required minimum distribution impacts.
Q5: Can Roth conversions help later?
Yes. Roth conversions allow you to move Traditional savings into Roth accounts during low-income years, helping manage taxes before retirement or RMD age.
Fiduciary, fee-only, Certified Financial Planner, Mike Turi

Mike Turi, CFP® APMA™ is the Founder and a Lead Financial Planner at Upbeat Wealth, a fee-only firm based in New Orleans and serving clients virtually across the country. He specializes in providing straightforward financial guidance to ambitious young families as they navigate life’s many milestones.

Do you have questions about what we shared in this post, or anything else in general? Feel free to schedule a free consultation or drop us a line!

Sign up for our newsletter (at the bottom of this page) to stay up to speed on our Upbeat Insight.

Disclaimer: All content in this article is provided for educational, general information, and illustration purposes only. None of the information is intended as investment, tax, accounting, or legal advice. Nor is it a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult with a financial planner, accountant, and/or legal professional for advice on your specific situation. Read our full disclaimer here.

Year-End Tax Planning: Smart Moves to Save You Money

Year-End Tax Planning Smart Moves to Save You Money

Ever feel like the holiday season is too quiet? Maybe not enough going on? Boring, even?

Well, I have a little gift for you. It’s the perfect time to add some year-end tax planning to your life!

And for a few reasons...

  • As the year comes to a close, you have a pretty good idea of what your actual income will look like, along with other variables that impact your tax outcome.
  • With the new year just around the corner, you likely have a sense of how things will look in comparison to the one that’s closing out.
  • Occasionally, in years such as this, there is new legislation that creates opportunities and/or hurdles to consider from one year to the next.

Here are 7 end-of-year tax planning strategies to consider as 12/31 approaches:

  1. Compare your total estimated tax bill to your actual taxes paid
  2. Top off tax-advantaged investment accounts
  3. Optimize 529s for state income tax deductions or credits
  4. Explore opportunities for tax-loss harvesting
  5. Consider tax-gain harvesting
  6. Assess the potential for Roth conversions
  7. Maximize your charitable donation strategy

Compare Your Total Estimated Tax Bill to Your Actual Taxes Paid Before December 31st

For starters, it’s helpful to have a heads-up on where you stand with Uncle Sam. Have you overpaid, putting you on pace for a large refund? Have you not paid enough to the IRS, potentially even exposing yourself to an underpayment penalty? Not only do we want to eliminate surprises, but also allow for enough time to make some final adjustments before the year closes. 

Most people – as employees of a company – have money automatically taken out of their paychecks to cover federal taxes and state taxes. But simply having it withheld doesn’t mean it’s the right amount, especially if you have other types of income aside from your salary. Other individuals, such as business owners, those with large amounts of investment income, or people with supplemental income like RSUs, may be making quarterly estimated tax payments. But again, as things shift throughout the year, it’s necessary to confirm you’ve been paying an appropriate amount.

End-of-year projections can be very powerful

Here at Upbeat Wealth, we run tax projections for all of our planning clients toward the end of the year to assess where they stand with the IRS. If you want to give it a shot on your own, check out the IRS’s tax withholding estimator tool.

At a minimum, you’ll want to be sure you’re going to cross over the Safe Harbor threshold

If you don’t give the IRS enough of your total tax liability during the calendar year, they will assess an underpayment penalty. The key here is that the IRS likes to get its taxes when the income is earned. To avoid a penalty, the IRS (and states) have the Safe Harbor rule for determining the minimum you need to pay. You won’t be penalized if you meet at least one of the following:

  • Owe less than $1,000 in tax for the current year.
  • Pay at least 90% of the total tax bill for the current year.
  • Pay at least 100% of the tax you owed for the previous year. This bumps up to 110% of the previous year’s tax bill for those with an AGI over $150k (over $75k if married filing separately).

Making sure you’re in the clear with this rule can protect you from paying any extra amount to the IRS in the form of penalties.

Top Off Tax-Advantaged Investment Accounts

Now is a great time to see how you’re doing with contributions to certain investment accounts that have a December 31st deadline for the tax year. These include:

  • Employee contributions to workplace retirement plans, such as a 401k, 403b, etc.
  • Health Savings Account (to make the contributions via payroll deductions, which allows you to avoid FICA taxes on the amount contributed)

These accounts have a maximum annual contribution limit set by the IRS (which is typically adjusted every year or two). If you’re not already on a path to hit that amount, consider adjusting your payroll deferral percentage to direct surplus cash flow into any of these accounts you have access to so you can get there by year’s end.

What are the annual IRS contribution limits?

  • 2025 Max for 401ks and 403bs
    • $23,500
    • + $7,500 for age 50+ ($31,000 total)
    • + $11,250 for ages 60-63 ($34,750 total)
  • 2025 Max for HSAs
    • Self-Only: $4,300 (+ $1,000 for age 55+)
    • Family: $8,550 (+ $1,000 per eligible spouse age 55+)

On a separate note, keep an eye on the balance in any Flexible Spending Accounts since these are of the “use-it-or-lose-it” variety. 

Optimize 529s for State Income Tax Deductions or Credits

If you’re saving into a 529 for your child’s education, or plan to, take a close look at your home state’s tax rules. Over 30 states offer either an income tax deduction or credit for contributions made to a 529 if it’s established through their own program. The available benefits are different from state to state.

Explore Opportunities for Tax-Loss Harvesting

If you have any losses in a taxable brokerage account, you can benefit from “capturing” (or harvesting) those investment losses. By selling a position that is in the red, you “realize” that loss (considered “unrealized” until a sale occurs) and can use it to offset other investment gains you may have realized during the year. If you don’t have any gains to knock down (or if your losses exceed your gains), you can use up to $3,000 of investment losses ($1,500 if filing MFS) to reduce your ordinary income for the year, carrying any remaining losses into future years for use.

Example:

Let’s say Marcus sold “investment X” earlier in the year for a gain of $5,000.

At the end of the year, he sells “investment Y” and realizes a loss of $12,000.

When preparing his taxes, he can use his $12k in losses to “offset” his $5k in gains. This results in a net $0 of investment gains for the year, thus no taxes on that investment income.

Now, he still has $7k of unused losses. He can use $3k of that to reduce his income for the year. Finally, he has $4k in losses that will carry forward to the next tax year.

The Finer Details

When doing the math, you have to first net short-term capital losses against short-term capital gains. Then, separately do the same with long-term capital losses and long-term capital gains. Next, you net those two amounts against each other (if you have a gain/loss for each).

At tax time, Form 8949 and Schedule D are used to report your capital gains and/or losses.

Be careful with the Wash Sale Rule

What the rule says: If you buy the same investment, or a “substantially identical” security, within a 30-day window before or after selling it at a loss, then that loss is disallowed. That means you miss out on the tax benefit. In other words, you cannot use that loss to reduce other investment gains or income. An important note is that the rule applies across all accounts that both you and your spouse own, if you’re married.

Crypto is different

Notably, the wash sale rule does not apply to cryptocurrency. Therefore, you could sell a cryptocurrency at a loss and then immediately repurchase it that same day while still being able to use that captured loss against other gains or income.

Consider Tax-Gain Harvesting

If your income is relatively lower this year compared to others (think: sabbatical, time between jobs, back in school, etc.), and you’ve moved down to a lower long-term capital gains tax bracket, then you may have a nice opportunity to sell appreciated taxable investments and pay taxes at a lower rate.

Did you know? In 2025, if your income is under $48,350 (single) or $96,700 (MFJ), you are in the 0% long-term capital gains tax bracket. Meaning you’d have the chance to sell some investments with a gain at a 0% tax rate!

2025 Long-Term Capital Gains Brackets

  • Single Filers
    • 0%: ≤ $48,350
    • 15%: $48,351 – $533,400
    • 20%: > $533,400
  • Married Filing Jointly
    • 0%: ≤ $96,700
    • 15%: $96,701 – $600,050
    • 20%: > $600,050

Assess the Potential for Roth Conversions

Do you have money in a pre-tax retirement account that you’d like to move over to a Roth? If so, there are a couple of times where doing so can make even more sense from a tax standpoint:

  • When you’re in a relatively lower-income year
  • When the stock market is down

Here’s another case where a lower-income year may bring some opportunity. In this case, you’ll want to focus on your ordinary income tax bracket, since this is what’s applied to any amounts converted from a pre-tax retirement account to a Roth. If you do find yourself in this position, you could consider taking advantage of any room left in that relatively lower tax bracket to pay less taxes on the conversion than you would in more “typical” years.

And if the stock market is down, resulting in a lower balance in the account, there’s simply less income produced in the process of converting, compared to when the account balance is higher. In other words, it makes the tax on the conversion cheaper.

If you plan on executing a Roth conversion, make sure you have the cash on hand to pay the tax bill.

Maximize Your Charitable Donation Strategy

If charitable giving is part of your routine, then it pays to examine your strategy through a tax lens as we near year’s end, especially in 2025. In particular, the passage of the OBBBA over the summer came with a handful of specific updates impacting how you should think about charitable donations. Let’s look at each here:

The standard deduction for this tax year is $15,750 (single) and $31,500 (MFJ).

  • Therefore, your total itemized deductions (which can include donations to charity) would need to exceed those levels in order for itemizing to save on taxes. 
  • If your typical single-year donation amount doesn’t move the needle on your total itemized deductions above the standard amount, then “bunching” might be worth exploring. This involves combining the amount you would normally donate across multiple years into a single one.

The cap for the state and local tax (SALT) deduction was raised from $10,000 to $40,000 (though it phases out for those with a MAGI of $500k and goes back down to $10k when MAGI hits $600k).

  • So for those with higher state and local taxes, that can much more easily push you into itemizing territory when adding in charitable contributions.

Beginning in 2026, you’ll only be able to deduct contributions that surpass 0.5% of your Adjusted Gross Income (AGI).

  • This means the same contribution will count for less on your taxes in 2026 than it will this year.
  • This is another reason for some filers to consider the “bunching” approach mentioned above. More specifically, moving what you’d normally donate in 2026 forward into 2025 and combining it with this year’s annual giving could easily produce a better tax outcome.

Also starting in 2026, itemized deductions will be capped at 35% for those in the 37% marginal bracket.

  • Therefore, charitable donations will be slightly less impactful from a tax standpoint for those in the top bracket after this year.
  • Yet another reason for those in the highest bracket to bunch into 2025.

For those who don’t itemize, starting in 2026, you will be able to deduct up to $1k (single) and $2k (MFJ) for donations directly to charity.

  • If your typical donation amount doesn’t move the needle with itemizing over taking the standard deduction, and you haven’t yet completed your giving for 2025, consider delaying to January. 
  • If you don’t itemize, you can take a deduction in 2026 that you wouldn’t get this year.

Lastly, here’s a general refresher on how to make the most of charitable donations, including the details on donating appreciated investments to a donor-advised fund, another fantastic tax-planning move!

Year-End Tax Planning FAQ

Q1: Why is tax planning so important at the end of the year?

The end of the calendar year is when you have the most complete picture of your income, deductions, credits, investment performance, and so on. You should also have a general idea of what those same variables will look like in the coming year for comparison. This allows you to make the most tax-informed decisions within your financial plan. 

Q2: What is year-end tax planning?

Year-end tax planning is the process of running projections and making adjustments before December 31st to reduce your current tax bill and avoid surprises at filing time.

Q3: Which accounts have a funding deadline of December 31st?

Any “employee” contributions to workplace retirement plans, such as 401ks and 403bs. Additionally, payroll deductions made to HSAs only count for the current year when made by 12/31 (though direct contributions can be made up until the tax filing deadline with FICA taxes owed on these amounts).

Q4: How do I avoid an IRS underpayment penalty?

You can avoid an underpayment penalty by meeting the IRS “safe harbor rule”, which can be done by paying at least 90% of your total current year tax liability, or at least 100% of the tax owed for the previous year. This jumps to 110% of the prior year’s tax bill if your AGI was over $150k (over $75k if married filing separately).

Q5: Is tax-loss harvesting worth it if I don’t have gains to offset?

Yes. If you don’t have capital gains, you can use up to $3,000 of investment losses each year to reduce ordinary income, with “unused” losses carried forward for use in future years.

Q6: When does a Roth conversion make sense?

Roth conversions often make the most sense in lower-income years or during market downturns, when the tax cost of converting those pre-tax dollars is relatively lower than it may be in other years (as long as you have the cash to pay the taxes).

Fiduciary, fee-only, Certified Financial Planner, Eddy Jurgielewicz

Eddy Jurgielewicz, CFP® is a Partner and Lead Financial Planner at Upbeat Wealth, a fee-only firm based in New Orleans and serving clients virtually across the country. He specializes in providing straightforward financial guidance to ambitious young families as they navigate life’s many milestones.

Do you have questions about what we shared in this post, or anything else in general? Feel free to schedule a free consultation or drop us a line!

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Disclaimer: All content in this article is provided for educational, general information, and illustration purposes only. None of the information is intended as investment, tax, accounting, or legal advice. Nor is it a recommendation for purchase or sale of any security, or investment advisory services. We encourage you to consult with a financial planner, accountant, and/or legal professional for advice on your specific situation. Read our full disclaimer here.