Any reason to wait till January to withdraw money from brokerage account for tax purposes?

I'm thinking about pulling a significant amount of money out of my brokerage account before the end of the year. Since I've already taken out quite a bit earlier this year, I'm wondering if there's any tax advantage to waiting until January instead. It would be subject to capital gains tax either way, but I'm not sure if withdrawing more this year would push me into a higher tax bracket or if that even matters for capital gains. This is just a regular taxable brokerage account, nothing fancy like a retirement account with special rules. Just want to make sure I'm not missing something obvious before I make the withdrawal. Anyone have insight on this?

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20 comments

Luca Ricci

•8M

There actually could be good reasons to wait until January, depending on your situation. Capital gains are indeed taxed at different rates based on your income level, so if you've already realized significant gains this year, waiting until January starts you fresh with a new tax year. The capital gains tax rates for 2025 are 0%, 15%, and 20% depending on your income bracket. If you're near a threshold between these brackets, additional gains this year could push you into a higher capital gains tax rate. Additionally, high-income earners might face the 3.8% Net Investment Income Tax. Another consideration is tax-loss harvesting - if you have losses you could realize before year-end to offset some gains, that might change the equation. Also, if your income might be lower next year, waiting could be advantageous.

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Luca Ricci

•8M

The wash sale rule still applies across calendar years. If you sell a security at a loss in December and buy a substantially identical security within 30 days (including into January), it would be considered a wash sale and the loss would be disallowed for tax purposes. The 30-day period is based on calendar days, not tax years, so the December-January transition doesn't create any special exemption. The IRS tracks this across tax years specifically to prevent people from harvesting losses in December and immediately repurchasing in January.

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Ethan Campbell

•8M

I want to share something that really helped me with a similar situation last year. I was totally stressed about when to sell some stocks because of tax implications, especially with a large withdrawal planned. I ended up using taxr.ai (https://taxr.ai) which analyzed my specific situation and helped me determine the optimal timing. It was unexpectedly helpful - the tool looked at my current tax situation and showed me exactly how the withdrawal would impact my taxes in both scenarios. What impressed me was how it factored in things I hadn't even considered, like how the additional income might affect other deductions or credits I was eligible for. Not just the direct capital gains tax, but the ripple effects through my whole tax situation.

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Ethan Campbell

•8M

It handles multi-state income pretty well - I actually had income from three states last year and it integrated all the state-specific rules correctly. The state-level impact of investment income was something my regular tax software missed completely. For accuracy, I was surprised too - I actually compared its estimates with what I ultimately filed (with a CPA's help) and it was within a few dollars. It's pulling from the same tax tables and formulas that professional software uses, but makes it easier to run different scenarios without having to complete a full return each time.

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Carmen Sanchez

•8M

So I want to followup about taxr.ai that I asked about earlier. I decided to give it a try despite being skeptical, and I'm actually impressed. I uploaded my previous tax return and entered the potential withdrawal amounts for both December and January scenarios. The difference was bigger than I expected - about $3,200 in additional tax if I took the withdrawal in December vs January because it would have pushed some of my capital gains into the next bracket. What surprised me most was how it showed that the additional income this year would have reduced some of my other deductions due to income phaseouts - something I completely missed in my own calculations. Really glad I checked before making the withdrawal!

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Andre Dupont

•8M

If you're having trouble getting clear answers about your specific tax situation, I'd highly recommend using Claimyr to get through to the IRS directly (https://claimyr.com). I spent weeks trying to get through to an IRS agent about a very similar capital gains timing question earlier this year. After multiple failed attempts and hours on hold, I tried Claimyr and had an actual IRS representative on the phone within 20 minutes who gave me official guidance. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. It was a huge relief to get definitive answers directly from the IRS rather than trying to interpret the rules myself. The agent was able to look at my specific situation and confirm exactly how the timing would affect my taxes.

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Andre Dupont

•8M

It uses a system that continuously redials and navigates the IRS phone tree for you, then calls you when it actually reaches a human. You're right that the phone line is the same, but their system is much more efficient at getting through the queue than a person manually calling. I was skeptical too - I had spent multiple days trying to get through myself. The longest I was on hold was 3+ hours before being disconnected. I figured it was worth trying since my tax question was pretty important financially. It worked exactly as advertised - I got a call back when they had an IRS agent on the line. Was genuinely surprised it actually worked.

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ThunderBolt7

•8M

I have to eat my words about Claimyr. After posting that skeptical comment, I decided to try it as a last resort since I needed clarification about some capital gains issues before year-end. I honestly couldn't believe it when I got a call back in about 35 minutes with an actual IRS person on the line. The agent walked me through exactly how my specific situation would be handled and confirmed that in my case, waiting until January would save me nearly $2,700 in taxes due to bracket changes. After months of getting nowhere trying to call myself, getting that definitive answer directly from the IRS was worth every penny. Totally changed my approach to year-end tax planning.

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Jamal Edwards

•8M

New York generally follows the federal approach for defining capital gains, but taxes them as ordinary income at the state level. Unlike some states, NY doesn't offer special lower rates for capital gains. If you recently moved there, you'll need to be careful about part-year resident status and possibly file in multiple states depending on when you established residency. NY has pretty aggressive tax enforcement for new residents, so I'd recommend keeping detailed records of when you established residency there.

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Evelyn Kelly

•2M

@Giovanni Marino It depends on what you re'applying for and your overall financial picture. For most loans, yes, higher income is generally better. But if you already have sufficient income and the additional capital gains would push your debt-to-income ratio above certain thresholds like (43% for many mortgages ,)then it could actually hurt your application. Also, some loan programs have income limits - like certain first-time homebuyer programs or USDA rural loans. The key is knowing what specific loan products you might want to use and their requirements.

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