Free Tax Planning Checklist: What to Review in June

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Free Tax Planning Checklist: What to Review in June

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By June, the tax season might feel like a distant memory, but for proactive individuals and business owners, it’s a golden opportunity. Mid-year tax planning is one of the smartest moves you can make to reduce your 2025 tax bill. Waiting until December (or worse, the following April) can mean missing out on deductions, credits, and strategies that could have significantly lowered your liability.

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This free tax planning checklist will guide you through everything you should review in June—from income adjustments to retirement contributions—so you stay ahead of the IRS and maximize your tax efficiency for the rest of the year.

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✅ 1. Review Your Income Sources

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• W-2 income: Are you on track to stay in your expected tax bracket?

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• Side gigs or freelancing? If you're earning income from gig work, it's subject to self-employment tax. Make sure you're saving accordingly.

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• Dividends or capital gains? If you’ve sold assets, calculate gains/losses now.

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• Rental property? Keep a record of your depreciation and expenses.

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➡️ TIP: Use the IRS Tax Withholding Estimator to see if you’re having enough (or too much) withheld from your paycheck.

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✅ 2. Adjust Your Withholding or Estimated Taxes

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If your income has significantly increased or decreased, you may need to:

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• Update your W-4 with your employer.

• Adjust your quarterly estimated tax payments if you're self-employed.

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2025 Estimated Tax Due Dates:

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• April 15, 2025

• June 16, 2025

• September 15, 2025

• January 15, 2026

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➡️ Learn more from the IRS on Estimated Taxes

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✅ 3. Evaluate Retirement Contributions

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Maximizing retirement contributions not only boosts your future wealth—it reduces your taxable income.

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2025 Contribution Limits:

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➡️ Compare IRA vs. 401(k) rules

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✅ 4. Reassess Your Filing Status

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Did your situation change in 2025? Common life events that may impact your filing status:

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• Marriage or divorce

• Having a child

• Death of a spouse

• Becoming a head of household

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Your filing status affects your standard deduction, income tax rates, and eligibility for tax credits.

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➡️ Check the IRS Filing Status Assistant

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✅ 5. Revisit Your Tax Deductions and Credits

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Now is the time to start optimizing deductions. Ask yourself:

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• Are you itemizing or using the standard deduction?

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2025 Standard Deduction:

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• Single: $15,000

• Married Filing Jointly: $30,000

• Head of Household: $22,500

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Common Deductions:

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• State & local taxes (SALT) – capped at $10,000

• Mortgage interest

• Medical expenses (over 7.5% of AGI)

• Charitable donations (to qualified 501(c)(3)s)

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➡️ See IRS Schedule A Instructions

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Key Tax Credits to Consider:

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• Child Tax Credit (CTC): Up to $2,000 per child under 17

• Child and Dependent Care Credit

• Education credits (AOTC & LLC)

• Saver’s Credit for low- to moderate-income earners contributing to retirement

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✅ 6. Plan for Capital Gains and Losses

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Tax-loss harvesting isn’t just for December. In June, review your portfolio:

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• Realized any gains? Offset them by selling underperforming assets.

• Consider holding appreciated assets for over a year to qualify for long-term capital gains (0%, 15%, or 20% depending on income).

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➡️ Capital Gains Tax Rates for 2025

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✅ 7. Update Business Expenses & Depreciation (If Self-Employed)

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Keep meticulous records—digitize receipts and log mileage.

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2025 Deduction Limits:

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• Standard Mileage Rate: 70¢/mile

• Section 179 Deduction: Up to $1,220,000 (phase-out at $3,050,000)

• Bonus Depreciation: 60% for qualified property

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➡️ IRS Publication 946 on Depreciation

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Also review:

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• Home office deduction

• Meals (50% deductible)

• Equipment/software costs

• Contractor payments (file 1099-NECs)

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✅ 8. Health Coverage and HSA Contributions

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2025 HSA Contribution Limits:

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➡️ IRS HSA Rules and Limits

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HSA Contributions Are Triple Tax-Advantaged: Tax-deductible, tax-deferred growth, and tax-free for qualified medical expenses.

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✅ 9. Double-Check IRS Notices or Adjustments

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Received any letters from the IRS? Don’t ignore them. June is a great time to handle:

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• Underpayment notices

• Identity verification requests

• CP2000 mismatches (for unreported income)

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➡️ How to Respond to an IRS Letter

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✅ 10. Start Preparing for Q3 Tax Moves

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Some moves require longer lead time. Begin considering:

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• Charitable contributions or donor-advised funds

• Large purchases eligible for write-offs

• Year-end bonuses or deferred income

• Converting Traditional IRAs to Roth IRAs (check marginal brackets)

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✅ Vincere Tax Pro Tip:

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“The best time to prepare for tax season is when no one else is thinking about it.”
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Tax planning isn't just about avoiding surprises. It’s about building a proactive financial strategy. Use this checklist as your June audit, and consult with a Vincere Tax advisor to dig deeper into opportunities tailored for you.

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Final Words

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June may be halfway through the year, but you still have plenty of time to make adjustments that matter. Whether it’s increasing your retirement savings, reducing your self-employment burden, or capturing tax credits before they expire, now is the time to get organized and ahead.

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Need Expert Help?

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Vincere Tax specializes in year-round proactive tax planning. From individuals to entrepreneurs, we help clients take full control of their financial future.

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➡️ Schedule your free consultation with Vincere Tax

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Frequently Asked Questions (FAQs)

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1. What happens if I underpay my taxes mid-year?

You may face underpayment penalties. Using the IRS Estimated Tax Worksheet can help you avoid surprises.

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2. Should I contribute to a Roth or Traditional IRA?

It depends on your income and future tax bracket. Traditional IRAs offer current-year deductions; Roths offer tax-free growth.

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3. How can I track deductions easily?

Use bookkeeping apps like QuickBooks, Expensify, or custom tracking tools to digitize and categorize your expenses.

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4. Can I still deduct my home office in 2025?

Yes—if you're self-employed. W-2 employees cannot claim the deduction under current law.

5. What’s the best way to plan for tax credits?

Start by identifying eligibility early (children, education, energy upgrades, etc.), and keep receipts/documentation organized for filing.

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I hope this information was helpful! If you have any questions, feel free to reach out to us here. I’d be happy to chat with you. 

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Vincere Tax can help you with the tax implications of business taxes, stocks, bonds, ETFs, cryptocurrency, rental property income, and other investments. 

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Being audited is comparable to being struck by lightning. You don't want to practice pole vaulting in a thunderstorm just because it's unlikely. Making sure your books are accurate and your taxes are filed on time is one of the best ways to keep your head down during tax season. Check out Vincere's take on tax season!

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This post is just for informational purposes and is not meant to be legal, business, or tax advice. Regarding the matters discussed in this post, each individual should consult his or her own attorney, business advisor, or tax advisor. Vincere accepts no responsibility for actions taken in reliance on the information contained in this document.