Kenneth J. Dean, CPA, CFP®, CFA, MST walks through the tax strategies worth reviewing right now, from capital loss carryforwards and QCDs to the 0% capital gains opportunity most people overlook. If any of these apply to your situation, this is the right time of year to have the conversation.

Tax season is a good time to take stock of where things stand and make sure nothing is being left on the table. Here is what we are focused on with clients right now. 

Capital Loss Carryforwards If your prior year return shows a capital loss carryforward, that number has value. Any capital gains you realize this year can be offset dollar-for-dollar against that carryforward. If losses still exceed gains after the offset, up to $3,000 can be deducted against ordinary income, with the remainder carrying forward into future years. If you have a carryforward sitting on your return and have not talked through how to put it to work, that conversation is worth having. 

Standard Deduction vs. Itemizing Most people take the standard deduction, and for many that is the right call. If your deductible expenses are close to the standard deduction threshold, there is a planning opportunity called bunching. The idea is to concentrate deductible expenses into a single tax year so the total clears the threshold and delivers an actual benefit, then take the standard deduction the following year. It takes some coordination but can add up meaningfully over time. 

QCDs for Clients Age 70½ and Older If you are 70½ or older and own an IRA, a Qualified Charitable Distribution is one of the most tax-efficient ways to give. In 2026, you can direct up to $111,000 from your IRA directly to a qualified charity. The distribution counts toward your required minimum distribution but is excluded from your taxable income entirely. For clients who are charitably inclined, this approach almost always produces a better outcome than writing a personal check. 

Estimated Tax Payments and a Smarter Alternative If you owe estimated taxes, the payment deadlines matter. Missing them triggers penalties. That said, withholding is often a cleaner solution than quarterly estimates for many clients. If you receive wages, Social Security benefits, IRA distributions, or pension income, adjusting the withholding on those payments can cover your liability without the quarterly paperwork. Worth reviewing before the first estimated payment comes due. 

Accelerating Capital Gains at 0% In 2026, if your taxable income falls below $49,450 as a single filer or $98,900 married filing jointly, your long-term capital gains rate is 0%. If your income is near or below those thresholds — or if you have a year where income is unusually low — deliberately realizing gains can be a smart move. You reset the cost basis on appreciated positions without paying tax. It requires some planning to execute correctly, but the opportunity is real.   

Municipal and Treasury Securities Two asset classes worth keeping in mind from a tax efficiency standpoint: municipal bonds are exempt from federal income tax, and Treasury securities are exempt from state income tax. Depending on your state tax rate and income level, the after-tax yield on either can be more attractive than the headline number suggests. This is especially relevant for clients in higher state tax brackets.  Municipal bonds are subject to availability and change in price. They are subject to market and interest rate risk if sold prior to maturity. Bond values will decline as interest rates rise. Interest income may be subject to the alternative minimum tax. Municipal bonds are federally tax-free but other state and local taxes may apply. If sold prior to maturity, capital gains tax could apply. 

The Bigger Picture Tax planning strategies work best, in our opinion, when they are connected to everything else — your investment portfolio, your cash flow, your estate plan, your long-term goals. At Winthrop Wealth, our Total Net Worth Approach philosophy helps us understand a client’s broader financial picture, and when appropriate we may discuss tax considerations as they relate to financial planning and investment decisions, in coordination with the client’s tax professional. 

If any of the above feels relevant to your situation, reach out. This is the right time of year to have the conversation.