Strategic Roth conversions (December 31 deadline)

What it is: Converting pre-tax IRA money to a Roth IRA. You pay taxes on the conversion now, but the money grows tax-free and you never pay taxes on it again—including your heirs if they inherit it.

Why coordination matters: Your CPA can project your taxable income for the year and identify how much room you have before hitting the next tax bracket. Your advisor can model how much to convert based on your investment timeline, estate planning goals, and future RMD obligations. If your income is unusually low one year—maybe you retired mid-year or had a business loss—that's the time to convert aggressively. But only if someone is watching both your tax return and your investment accounts.

Timing: Conversions must be completed by December 31. Once the year ends, the opportunity is gone. You can't go back in January and say "I should have converted more last year."

Qualified charitable distributions (age 70½+, December 31 deadline)

What it is: If you're over 70½, you can donate up to $100,000 directly from your IRA to charity. The distribution counts toward your RMD, but it's not included in your taxable income.

Why coordination matters: Most retirees take their RMD as cash, pay taxes on it, and then write a check to charity. That's backwards. If your CPA knows you're charitably inclined and your advisor knows you need to take an RMD, the QCD strategy becomes obvious. But if no one's coordinating, you miss it.

Timing: The distribution must come out of your IRA by December 31 to count for that tax year. If you wait until January, you've missed the window for the prior year.

Timing capital gains to avoid the Net Investment Income Tax (planning throughout the year)

What it is: The Net Investment Income Tax (NIIT) is a 3.8% surtax on investment income (capital gains, dividends, interest, rental income) for individuals with modified adjusted gross income over $200,000 (single) or $250,000 (married filing jointly). If you're over the threshold, you're paying an extra 3.8% on top of your regular capital gains rate.

Why coordination matters: Your CPA can track where you stand relative to the NIIT threshold throughout the year. Your advisor can control when capital gains are realized—by timing asset sales, managing rebalancing, and coordinating distributions. If you're close to the threshold, your advisor can delay realizing gains until the following year, or harvest losses to offset gains and keep you under the limit.

Let's say you're married and your income is $240,000. You're $10,000 below the NIIT threshold. If your advisor rebalances in November and realizes $50,000 in capital gains without knowing your income situation, you've just triggered the 3.8% surtax on $40,000 of those gains—costing you an extra $1,520 in taxes that could have been avoided by waiting until January.

Your CPA sees the problem in April when preparing your return, but by then it's too late. Your advisor had no idea you were close to the threshold because they weren't looking at your tax return. That's what happens when no one's coordinating.

Timing: Capital gains are recognized in the year the sale settles. If you sell on December 30 and it settles January 2, that's next year's tax return. You have flexibility on when to realize gains throughout the year, but once December 31 hits, it's locked in. The goal is to manage gains proactively so you're not surprised by the NIIT in April.

Bunching itemized deductions (state and local taxes, charitable giving, medical expenses)

What it is: Instead of spreading deductions evenly across years, you concentrate them into a single year to exceed the standard deduction, then take the standard deduction in other years.

Why coordination matters: Your CPA can model whether bunching makes sense based on your income and deductions. Your advisor can help you bunch charitable contributions by front-loading multiple years of giving into a donor-advised fund in one year, taking the big deduction, and then distributing the funds to charities over time.

Timing: Charitable contributions must be made by December 31. Prepaying state taxes only works if the taxes are assessed in the current year (you can't prepay 2026 taxes in 2025 just to get the deduction early). Medical expenses need to be paid by December 31, not just incurred.

Tax-efficient asset location (ongoing strategy, implemented when investing)

What it is: Holding tax-inefficient investments (like bonds or high-dividend stocks) in tax-deferred accounts, and holding tax-efficient investments (like index funds or growth stocks) in taxable accounts.

Why coordination matters: Your advisor should know which accounts to use for which investments. Your CPA should be reviewing your tax return to see if you're paying unnecessary taxes on interest or dividends that could have been sheltered. If you're holding bonds in a taxable brokerage account and index funds in your IRA, you're doing it backwards.

Timing: This isn't deadline-driven, but it matters every year. The longer you hold tax-inefficient assets in the wrong accounts, the more you're paying in unnecessary taxes.

Timing Social Security and pension withdrawals (before you start, not after)

What it is: Deciding when to start Social Security (age 62, full retirement age, or 70) and how to coordinate that with pension income, IRA withdrawals, and other income sources.

Why coordination matters: Starting Social Security early reduces your monthly benefit, but it might make sense if it allows you to delay IRA withdrawals and do more Roth conversions in lower-tax years. Your CPA can model the tax impact of different strategies. Your advisor can model the investment and longevity implications. The right answer is somewhere in the middle, and you only get there if both are involved.

Timing: Once you start Social Security, you can't easily undo it (you have a 12-month window to reverse, but after that you're locked in). This decision needs to be made before you file, not after.

Net unrealized appreciation (NUA) for company stock (at retirement or separation, one-time decision)

What it is: If you have highly appreciated company stock in your 401(k), you can move it to a taxable account and pay ordinary income tax only on your cost basis. The appreciation is taxed at capital gains rates when you eventually sell, which can save a lot compared to rolling everything into an IRA and paying ordinary income tax on all of it.

Why coordination matters: Your CPA needs to model the immediate tax hit versus the long-term savings. Your advisor needs to evaluate whether holding concentrated company stock makes sense from a risk perspective. If no one's coordinating, you'll probably just roll everything into an IRA by default and lose the option forever.

Timing: NUA must be elected at the time of distribution from the 401(k). Once you roll the stock into an IRA, you can't go back and use NUA later. This is a one-time decision that has to be made correctly the first time.

Required minimum distributions (RMDs) and the tax torpedo (starts at age 73, December 31 deadline)

What it is: Once you turn 73, you're required to start taking distributions from pre-tax retirement accounts. Those distributions are taxed as ordinary income and can push you into higher brackets, increase Medicare premiums, and cause more of your Social Security to be taxed.

Why coordination matters: Your CPA can calculate your RMD. Your advisor can help you plan for it—by doing Roth conversions earlier to reduce future RMDs, by positioning assets to generate the distributions tax-efficiently, and by coordinating RMDs with other income sources to manage your bracket.

Timing: RMDs must be taken by December 31 each year (except your first RMD, which can be delayed until April 1 of the following year—but that means taking two RMDs in one year, which usually makes your tax situation worse). Miss the deadline and you owe a 25% penalty on the amount you should have withdrawn.

Medicare IRMAA—the hidden tax on high earners in retirement (based on prior year income)

What it is: IRMAA stands for Income-Related Monthly Adjustment Amount. If your modified adjusted gross income exceeds certain thresholds, you pay significantly higher premiums for Medicare Part B and Part D. Most people pay the standard Medicare premium (around $174/month for Part B in 2024), but IRMAA can push that to $244, $349, $454, $559, or even $628 per month per person depending on your income.

For a married couple at the highest IRMAA tier, that's an extra $10,000+ per year in Medicare premiums on top of what they'd normally pay. And it's based on your income from two years prior—so what you do in 2024 affects your 2026 Medicare premiums.

Why coordination matters: IRMAA is triggered by the same things that show up on your tax return: Roth conversions, capital gains, RMDs, pension income, rental income. Your CPA can model where you stand relative to the IRMAA cliffs. Your advisor can help you time income to avoid pushing over the threshold unnecessarily.

Let's say you're married and your MAGI is $204,000. You're $2,000 below the first IRMAA threshold of $206,000. If your advisor rebalances your portfolio and realizes $10,000 in capital gains without knowing your income situation, you've just pushed yourself into the next IRMAA tier—costing you an extra $1,400 per year (per person) in Medicare premiums for the next year. That's $2,800 total for a couple, and it recurs every time you cross the threshold.

The IRMAA brackets create cliffs where an extra dollar of income can cost you thousands in Medicare premiums. The thresholds (for 2024, based on 2022 income) are:

• $103,000 (single) / $206,000 (married): First tier, adds ~$70/month per person

• $129,000 / $258,000: Second tier

• $161,000 / $322,000: Third tier

• $193,000 / $386,000: Fourth tier

• $500,000+ / $750,000+: Top tier

If you're planning a large Roth conversion, selling a business, or taking a big distribution, your CPA and advisor need to model the IRMAA impact. Sometimes it makes sense to spread the income over multiple years to avoid the higher premiums. Sometimes it's worth paying the premium to get the tax benefit. But you can't make that decision if no one's looking at both sides.

Timing: IRMAA is based on your income from two years ago. So if you want to avoid higher premiums in 2026, you need to manage your 2024 income now. If your income drops significantly (retirement, loss of pension, etc.), you can appeal to Social Security for a reduction, but it's easier to plan proactively than fix it retroactively.

Estimated tax payments (quarterly deadlines: April 15, June 15, September 15, January 15)

What it is: If you have income that isn't subject to withholding (capital gains, business income, rental income), you're supposed to pay estimated taxes quarterly to avoid underpayment penalties.

Why coordination matters: Your advisor knows when you're realizing capital gains from portfolio rebalancing or selling assets. Your CPA knows how much you owe and when payments are due. If they're not talking, you either overpay (tying up cash unnecessarily) or underpay (and owe penalties).

Who calculates and sends them? Here's where coordination becomes critical. Your CPA knows your total tax liability. Your advisor knows your investment income, capital gains, and when distributions happen. But who's responsible for making sure quarterly payments are calculated correctly and sent on time?

In most cases, your CPA calculates what you owe based on the prior year's return and current year projections. But by the time they see your Q1 investment income or capital gains, the Q1 payment deadline (April 15) might have already passed. If your advisor executes a large Roth conversion in November, does your CPA know to adjust your Q4 payment before the January 15 deadline?

When your CPA and advisor work together, this coordination happens proactively. Your advisor shares investment activity throughout the year—capital gains realized, Roth conversions executed, income distributions taken. Your CPA uses this information to adjust estimated payment calculations before deadlines pass. You're not scrambling in December to figure out if you've paid enough. You're not getting penalty notices in April because a Q2 payment was calculated based on outdated information.

Timing: Estimated taxes are due four times a year. If you realize a big capital gain in November, you can't wait until January to make the payment—you need to adjust your Q4 estimate by January 15 or you'll owe a penalty.

Tax-loss harvesting (ongoing, year-round with December 31 deadline)

What it is: Selling investments that have declined in value to realize losses that offset capital gains dollar-for-dollar. Any excess losses can offset up to $3,000 of ordinary income per year, and remaining losses carry forward indefinitely to future years. You can immediately reinvest in a similar (but not identical) asset to maintain your market exposure.

Why coordination matters: Most people think of tax-loss harvesting as a way to save $3,000 in ordinary income—which at a 24% tax bracket saves you $720. That's fine, but it's missing the bigger opportunity.

The real value comes from offsetting capital gains. Let's say you sold a rental property in March and realized a $200,000 capital gain. Without coordination, your advisor has no idea this happened. They manage your portfolio, see that some positions are down, but don't harvest the losses because there's no immediate need.

Meanwhile, you're about to owe capital gains tax on $200,000 at 15% federal ($30,000) plus 3.8% NIIT ($7,600) plus state taxes. If your advisor had known about the rental property sale, they could have harvested $200,000 in losses from your portfolio throughout the year to completely offset the gain. That's $37,600+ in federal taxes alone that you didn't need to pay.

Even if you don't have gains this year, harvested losses carry forward. If you harvest $50,000 in losses during a market downturn, you're building a "tax loss bank" that can offset future gains from rebalancing, required minimum distributions, or the sale of appreciated assets. Your CPA knows if you have loss carryforwards sitting on your return. Your advisor needs to know that so they can be strategic about when to realize gains.

Timing: Losses can be harvested throughout the year whenever positions are down, but the trades must settle by December 31 to count for the current tax year. The best practice is to monitor for opportunities year-round, not just wait until December when you might have fewer loss positions available or face year-end trading deadlines.

Year-end tax planning meetings (October–November, before it's too late)

Here's what almost never happens: in October or November, your CPA and financial advisor get on a call together, review your current-year income and tax situation, and identify opportunities that still have time to be executed before December 31.

Here's what usually happens: your CPA prepares your return in March, tells you what you owe, and says "let's try to do better next year." Your advisor manages your portfolio throughout the year without knowing your tax situation. And nobody realizes until April that you could have harvested losses, converted to a Roth, made a QCD, or bunched charitable contributions—but now it's too late.

The strategies that lower your taxes don't happen automatically. They require someone to look at your tax return, look at your investment accounts, model out scenarios, and execute on the strategies that make sense before the deadlines pass.

What coordination actually looks like

When your CPA and financial advisor work together, here's what changes:

Your advisor isn't just managing a portfolio—they're managing it with your tax situation in mind. They know when to harvest losses, when to realize gains, and which accounts to pull from based on what's happening on your tax return.

Your CPA isn't just preparing a return—they're proactively identifying strategies throughout the year and coordinating with your advisor to implement them before deadlines pass.

And you're not the middleman trying to remember what your CPA said and relay it to your advisor, or vice versa. The professionals are talking directly, and you're benefiting from strategies that only work when both sides are involved.

The difference isn't small. For someone with a few million in assets, the tax savings from proper coordination can easily be $20,000–$50,000+ per year. Multiply that over a decade or two, and it's one of the highest-return "investments" you'll ever make.

If you're paying a lot in taxes and suspect your CPA and advisor aren't coordinating, let's talk.