Beyond Tax Deadlines: Smart Strategies for the Months Ahead

As I write this, we're wrapping up one of the busiest stretches of the year in the tax world. September 15 marks the deadline for extended corporate and partnership tax returns, while October 15 is the due date for extended individual tax returns.

For many people, these deadlines pass without much notice. For our higher-net-worth and family office clients, however, this season involves months of gathering information, reviewing strategies, coordinating with multiple professionals, and ensuring every opportunity is properly captured.

In truth, much of my time since July has been devoted to helping clients navigate this process. The work can be complex, but it's also when some of the most valuable planning opportunities are uncovered.

As we move toward year-end, here are a few items worth reviewing for yourself and your family.

Don't Miss the New Above-the-Line Charitable Deduction

One of the more attractive provisions in the One Big Beautiful Bill (OBBB) is the ability to claim up to $2,000 of charitable contributions as an above-the-line deduction.
There is an important catch: the gift must be made in cash directly to a qualified charity. Contributions made through a Donor Advised Fund (DAF) do not qualify for this particular deduction.

My personal approach is simple. I plan to make this gift early in the year, check the box, and then handle the remainder of my charitable giving through my Donor Advised Fund.

If charitable giving is already part of your financial plan, make sure you're structuring gifts in a way that captures every deduction available.

Consider Using a Donor Advised Fund for Appreciated Investments

While a Donor Advised Fund may not qualify for the new above-the-line deduction, it remains one of the most powerful charitable planning tools available.

If you own appreciated stocks, ETFs, mutual funds, or certain private investments, you may be able to contribute those assets directly to a DAF. Doing so can allow you to:

• Receive a charitable deduction
• Avoid paying capital gains tax on the appreciation
• Create a pool of funds for future charitable giving

I personally used this strategy in 2026 after two private investments became publicly traded. Rather than sell and incur capital gains taxes, I contributed a portion of the appreciated shares to my Donor Advised Fund and used those funds for future charitable giving.

For charitable individuals and families, this can be one of the most tax-efficient giving strategies available.

Has Your Income Declined?  It May Be a Great Time to Look at a Roth Conversion

Many people assume Roth conversions are only for retirees, but some of the best opportunities arise when income temporarily declines.
Examples include:

• Retirement of one spouse
• Job loss or career transition
• Sale of a business
• A year with unusually low income
• Reduced consulting or bonus income

A Roth conversion allows you to voluntarily pay tax today at your current tax rate and move assets into a Roth IRA where future qualified withdrawals can be tax-free.
In addition, Roth IRAs are not subject to Required Minimum Distributions (RMDs) during your lifetime. This can help provide greater control over future taxable income and potentially reduce the likelihood of being pushed into higher tax brackets later in retirement.

Every situation is different, but for the right individual, a Roth conversion can be one of the most valuable long-term planning opportunities available.

If you've experienced a change in income this year, it may be worth running the numbers.

Don't Forget the Age 65+ Deduction

One of the simplest planning opportunities is often the easiest to overlook.
If you are age 65 or older, be sure you're taking advantage of the additional deduction available to seniors.

We've already identified several situations where clients were unaware of how the deduction applied to their circumstances. A quick review with your tax professional can ensure you're receiving the full benefit.

A Better Home for Cash?

One final idea that is not tax related.
For years, we've watched many investors leave substantial cash balances sitting in bank accounts earning little to no interest. While rates have improved from the lows of recent years, the average bank continues to pay far less than many available alternatives.

That is one reason we've begun offering cash management solutions to clients.
These programs are designed to provide flexibility, liquidity, and potentially higher yields than traditional checking and savings accounts. Current minimums begin at $25,000, and we're rolling out several options to accommodate different client objectives.

This is a newer offering for our firm, and you'll be hearing more about it in the months ahead.

Final Thoughts

Tax planning isn't something that happens only during tax season. In many cases, the most valuable opportunities are identified long before a return is filed.

Whether it's maximizing charitable deductions, utilizing a Donor Advised Fund, exploring a Roth conversion, capturing new deductions available under current law, or simply earning a more competitive return on cash, a little planning today can often produce meaningful results tomorrow.

If you'd like to discuss any of these strategies and whether they fit your situation, we'd be happy to help.

The best tax return is often the one that started with good planning months before it was filed.

​Important Disclosure: The information contained in this article is for educational purposes only and is not intended as personalized tax, legal, or investment advice. The effectiveness of any tax or financial planning strategy depends on an individual's specific circumstances. Before taking action, consult with your tax advisor, CPA, attorney, or other qualified professional regarding your personal situation. InTrust Advisors does not provide legal or accounting services.
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Tax laws and regulations are subject to change and interpretation.