ON-DEMAND WEBINAR REPLAY
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Watch the full Q4 Planning Deadlines - Roth Conversions & Tax-Loss Harvesting webinar replay and download the presentation deck from Windward Private Wealth Management. Continue exploring intentional, confident wealth guidance built to last across generations.
Recorded September 22, 2026
SECTION 1 - WATCH
Webinar Replay
Stream the full Q4 Planning Deadlines - Roth Conversions & Tax-Loss Harvesting presentation at your convenience. Pause, rewind, and revisit the moments that mattered most to your financial picture.
SECTION 2 - DOWNLOAD
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Download the full slide deck to review the key strategies, charts, and planning frameworks shared during the webinar. Share with family members, your CPA, or your attorney as you continue the conversation.
SECTION 3 - FAQs
Webinar FAQs
Answers to the questions we hear most about year-end tax strategy — straight from our September webinar on Roth conversions and tax-loss harvesting. If you'd like to talk through how any of this applies to your own situation, we'd welcome the conversation.
Roth Conversions
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What is a Roth conversion?
A Roth conversion moves money from a traditional IRA or 401(k) into a Roth IRA. You pay ordinary income tax on the converted amount in the year you convert. From that point forward, the money grows tax-free, and qualified withdrawals in retirement are tax-free as well.
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The goal is usually to convert enough to use the room remaining in your current tax bracket, without spilling into the next one. Converting a round number without checking your bracket is one of the most common mistakes we see. We model each conversion against your actual year-to-date income rather than a general rule of thumb.
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Yes — December 31st. Unlike an IRA contribution, which can be made up until the following April, a Roth conversion must be fully completed by the last business day of the calendar year. There is no extension.
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It can. Medicare's income-related premium surcharge (IRMAA) is based on income from two years earlier, so a larger conversion this year could affect your premiums two years from now. This is one of the reasons we look at your full picture before recommending a conversion amount, not just the immediate tax bill.
Tax-Loss Harvesting
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If you hold investments in a taxable brokerage account and some positions are worth less than what you paid, you can sell them to realize a loss. That loss offsets capital gains elsewhere in your portfolio, dollar for dollar. If your losses exceed your gains for the year, up to $3,000 of the excess can offset ordinary income, with any remainder carried forward to future years.
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No. You can reinvest the proceeds right away — you just can't buy back the identical investment, or one considered “substantially identical,” within 30 days before or after the sale. That's the wash sale rule, covered next.
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If you sell an investment at a loss and buy the same or a substantially identical investment within 30 days before or after the sale, the loss is disqualified. This trips people up most in late December, when there is little time left to correct it. A similar fund from a different provider can still count as substantially identical, so it's worth checking before you repurchase.
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The trade has to settle within the calendar year to count for that tax year. Most U.S. stock and ETF trades now settle one business day after the trade date (T+1), so earlier is still safer than later — waiting until the last few trading days of December leaves little room to fix a wash sale mistake or absorb an unexpected settlement delay.
How the Two Strategies Connect
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Only partially — and it's a common misconception that it offsets more than it does. A capital loss has to net against capital gains first; only up to $3,000 of any loss left over after that can offset ordinary income, including conversion income, in a given year. The more meaningful connection is less direct: if you're also realizing capital gains that year — from rebalancing a portfolio or selling shares to help cover the conversion's tax bill — those gains and the conversion are competing for the same tax-bracket room. Harvesting losses to absorb those gains frees up more of that room for the conversion.
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Not necessarily. The two strategies work well together when the opportunity exists, but a Roth conversion can make sense entirely on its own. We evaluate each independently, then look at whether pairing them adds value in your specific year.
Next Steps
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Tax situations change year to year — income, portfolio performance, and tax law can all shift what makes sense. We recommend revisiting both conversions and harvesting opportunities annually rather than treating either as a one-time decision.
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Talk with your Windward team well before the holidays. Once wash sale windows, custodian processing times, and busier December calendars are factored in, the actual decision-making runway is shorter than it looks in September or even November.
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This handout is educational, not personalized advice — everyone's tax situation is different. If you'd like to talk through your own numbers, we'd welcome the conversation.
SECTION 4 - CONTINUE
Your Next Step
Have questions inspired by the webinar? Our team is here to listen and help map a plan that's uniquely yours.
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Discovery Meeting
A complimentary, no-pressure conversation about your goals and current plan.
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Ask the Advisors
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Call the Office
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