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Maximize Your Year-End Individual Tax Strategies

The holiday season is quickly approaching, but before you dive into festive cheer, it’s crucial to consider some strategic year-end tax planning for your 2025 tax return. By evaluating your financial situation now, you can make the most of several last-minute tax planning opportunities. Here are some important considerations:

Determining the Necessity of Filing a 2025 Tax Return - If your 2025 income level means you’re not required to file, seize the opportunity to realize more income—tax-free. For example, sell appreciated stock without incurring a tax liability or take a penalty-free IRA distribution if eligible. Even if you’re not mandated to file, submitting a tax return might reveal substantial refundable credits you wouldn’t want to miss out on.

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Managing Unusually Low Income Years - A dip in income can present an ideal moment to convert a traditional IRA to a Roth IRA. The lower tax rates during these years can facilitate significant savings upon conversion, especially if you hold depreciated stocks in the account.

College-Age Children - If you’re eligible for education credits such as the American Opportunity or Lifetime Learning credits, ensure you’ve maximized your qualified tuition payments for 2025. Consider prepaying tuition for the first quarter of 2026 if necessary to heighten your credit claim for this tax year.

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Selling Your Home - If you sold your main residence and meet ownership and occupancy tests, your gains might be tax-exempt up to $250,000 (or $500,000 for joint filers). Failing to meet these criteria doesn’t eliminate your exclusion possibilities. Circumstances like employment relocation or health can qualify you for a partial exclusion.

Health-Related Accounts - If you’ve been eligible to contribute to a Health Savings Account (HSA) or have an underfunded health flexible spending account (FSA), reassess your contributions. Optimize your pre-tax savings by maxing out these accounts where possible, given the 2025 FSA carryover allowance.

Boosting Retirement Contributions - Ensure you’re contributing the maximum allowable amounts to your retirement plans. Missing this window means lost tax-deferred growth potential. Take full advantage of employer contribution matches as well.

Retirement Catch-Up Contributions - If you’re aged 60-64 in 2025, explore enhanced catch-up contribution limits for retirement plans. These amount to 150% of the standard limit and allow significant growth of your retirement nest egg.

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Anticipated Year-End Bonuses - If expecting a job-related bonus, consider deferring the income to next year if it benefits your tax situation by negotiating with your employer.

Required Minimum Distributions (RMDs) - For those aged 73 and older, ensure RMDs from retirement accounts align with the IRS mandates to avoid penalties. If 2025 is your first RMD year, remember you have until early next year to comply, but this could result in dual distributions for 2026, impacting tax liability.

Dealing with Investment Losses - With stocks down, sell underperforming ones to offset capital gains. Mind the wash sale rules to fully leverage these losses.

Appreciated Stocks Strategy - Low-income years might make selling long-held stocks more attractive due to favorable long-term capital gains rates.

Prepaying State and Local Taxes - The raise in the SALT deduction cap allows strategic prepayments of state and property taxes to optimize deductions for 2025.

Strategizing Charitable Contributions - You can boost 2025’s charitable deductions by planning donations carefully. Consider the impeding introduction of a deduction floor in 2026 to determine timing.

Leverage Qualified Charitable Distributions (QCDs) - IRA owners aged 70½ and older can transfer funds directly to charities tax-free, counting toward RMDs but not taxable income.

Maximizing Deduction on Medical Bills - To maximize 2025 deductions, aim to consolidate medical payments exceeding 7.5% of your AGI within this year.

Employing the Annual Gift Tax Exclusion - Utilize the $19,000 per person gift tax exclusion by the end of 2025 to distribute wealth without tax implications.

Avoiding Underpayment Penalties - Assess if there’s been a tax withholding shortfall this year, and if so, increase your withholding promptly to cover potential liabilities.

Claiming Disaster Losses - Utilizing tax claims for unreimbursed disaster-related losses can offer significant relief post-event. Ensure comprehensive assessment for the best year impact.

Our firm, ChesebroCPA, is committed to helping clients implement these strategies to reduce tax stress and increase clarity. Feel free to reach out for personalized advice as we approach the close of the year.

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