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Last-Minute Tax Strategies to Maximize Deductions Before Tax Day

As the tax deadline looms, it’s not too late to make smart financial moves that could lower your taxable income and keep more money in your pocket. Whether you're a small business owner, a freelancer, or simply looking to reduce your personal tax liability, these last-minute tax strategies can help you finish strong.
 
1. Max Out Retirement Contributions
If you haven’t already done so, consider contributing to a Traditional IRA. For 2024 taxes (filed in 2025), you can contribute up to:
  • $6,500 if you're under 50
  • $7,500 if you're 50 or older
Contributions made before April 15, 2025, can still count toward your 2024 tax return and may be deductible depending on your income and whether you’re covered by a retirement plan at work.
If you're self-employed, consider contributing to a SEP IRA—up to 25% of compensation or $66,000, whichever is less.
 
2. Fund a Health Savings Account (HSA)
If you’re enrolled in a high-deductible health plan (HDHP), you can contribute to an HSA until the tax filing deadline:
  • $3,850 for individuals
  • $7,750 for families
  • Additional $1,000 catch-up contribution if you're 55 or older
HSA contributions are tax-deductible, grow tax-free, and can be withdrawn tax-free for qualified medical expenses. It’s one of the most powerful tax-advantaged tools available—not just for covering healthcare costs today, but also for planning future care in retirement.
What You Can Pay for With Your HSA (That May Surprise You)
Many people don’t realize how expansive the list of eligible expenses is—especially for those prioritizing long-term health, mobility, and active living.
Fitness, Recovery & Mobility Support
  • Physical therapy and rehabilitation programs
  • Massage therapy (when prescribed for a medical condition)
  • Chiropractic care
  • Acupuncture and cupping treatments
  • Orthopedic shoes and custom orthotics
  • Compression socks and sleeves (for circulation or varicose veins)
  • Mobility aids such as canes, walkers, and wheelchairs
  • Exercise equipment (when prescribed by a doctor)
  • Balance training devices, posture correctors, and ergonomic supports
Wellness & Preventative Care
  • Mental health counseling and therapy
  • Sleep studies, CPAP machines, and medically necessary sleep aids
  • Nutritional counseling (if related to a diagnosed condition)
  • Dental and vision care (including exams, glasses, contacts, and procedures)
  • Travel for medical care, including lodging (up to $50/night) and transportation
  • LASIK eye surgery
  • Weight-loss programs (when prescribed for a medical condition)
  • Health coaching (if medically recommended)
  • Over-the-counter items such as first-aid kits, joint braces, hot/cold therapy packs, and thermometers
  • Medical cannabis (where legally prescribed)
  • Long-term care insurance premiums (within IRS limits)
  • Home modifications (such as grab bars or widened doorways, if medically necessary)
Pro Tip: Even if you don’t use your HSA this year, you can reimburse yourself years later for qualified expenses—as long as the HSA was open at the time and you keep your receipts.
 
3. Deduct Charitable Contributions
If you itemize deductions, don’t forget to tally up any charitable donations made in 2024. Last-minute gifts to qualified nonprofits—whether cash, appreciated assets, or goods—can reduce your taxable income.
Tip: For donated clothing, furniture, or other goods, be sure to have a receipt and estimate the fair market value.
 
4. Prepay Certain Expenses
If you're self-employed or own a small business, consider prepaying deductible expenses such as:
  • Business insurance
  • Office supplies
  • Subscriptions or marketing services
As long as the payment is made before the end of the tax year, you can deduct it for 2024.
 
5. Harvest Capital Losses
If you sold investments at a loss, those losses can offset capital gains—and up to $3,000 of ordinary income if your losses exceed your gains.
Be mindful of the wash sale rule: you cannot repurchase the same (or a substantially identical) investment within 30 days, or the loss will be disallowed.
 
6. Review Energy-Efficient Home Upgrades
If you made qualifying improvements—like installing solar panels, high-efficiency HVAC systems, or heat pumps—you may be eligible for energy tax credits under the Inflation Reduction Act. These credits reduce your tax liability dollar-for-dollar.
 
7. Contribute to a 529 Plan (State-Specific)
While not deductible on your federal return, many states offer deductions or credits for contributions to 529 college savings plans—and they may count if made before your state’s tax deadline.
Creative and Lesser-Known Uses for 529 Funds
  • K–12 tuition (up to $10,000 per year)
  • Registered apprenticeship programs (tools, books, fees)
  • Student loan repayment (up to $10,000 per beneficiary, plus $10,000 per sibling)
  • Accredited online or trade schools
  • Room and board, even off-campus (if student is enrolled at least half-time)
  • Technology and equipment required for school (laptops, printers, internet access)
Tip: If the funds aren’t used, you can change the beneficiary to another qualifying family member—including siblings, cousins, or even yourself—without penalty.
 
8. Gather All Eligible Deductions
Before filing, make sure you’ve accounted for:
  • Mortgage interest and property taxes
  • Medical expenses (if they exceed 7.5% of your adjusted gross income)
  • Educator expenses (up to $300 per teacher or $600 for two qualifying spouses)
  • Student loan interest (up to $2,500)
 
9. Use the Home Office Deduction (If You Qualify)
If you're self-employed and work from home, you may be able to deduct a portion of your rent or mortgage, utilities, insurance, and internet.
Choose from:
  • Simplified method: $5 per square foot (up to 300 sq. ft.)
  • Actual expense method: a percentage of actual home expenses
Note: This deduction is not available to W-2 employees, even if working remotely.
 
10. Deduct Business Mileage
If you used your personal vehicle for business in 2024, the IRS allows a deduction of 65.5 cents per mile.
Make sure you’ve kept a mileage log that includes:
  • Date
  • Purpose of the trip
  • Miles driven
11. Revisit the Qualified Business Income (QBI) Deduction
The QBI deduction allows many sole proprietors, LLCs, and S-corp owners to deduct up to 20% of their net business income on their personal return.
However, eligibility depends on income level, business type, and whether your business pays wages or owns qualifying property. For 2024, phaseouts begin at $191,950 (single) and $383,900 (married filing jointly). A tax advisor can help you structure your business to maximize this powerful deduction.
 
12. Explore the Saver’s Credit
If you contributed to a retirement plan and your income falls within the IRS thresholds, you may qualify for the Saver’s Credit—up to $1,000 ($2,000 if married filing jointly). This is a credit, not a deduction, meaning it directly reduces your tax bill.
 
Bonus Tip: File an Extension—But Don’t Delay Payment
You can file for a six-month extension using IRS Form 4868. This gives you more time to file your return—but not more time to pay. Estimate your liability and submit payment by April 15 to avoid penalties and interest.
 
Final Thoughts
Taxes don’t have to be stressful—especially when you approach them strategically. These last-minute moves can help reduce what you owe, fund your future, and keep more of your money working for you. If you’re unsure where to start or if you want to maximize your deductions safely, it’s well worth speaking with a trusted tax advisor before the deadline.

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