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Grace Johnson

Do I owe taxes on profits from a $71,000 loss due to wash sales?

So I'm freaking out a bit over my tax situation. Been trading pretty actively this year in my brokerage account. Made some good trades but also got caught in a pattern of buying and selling the same stocks within 30 days. Just got my tax docs and apparently I've got around $71,000 in wash sale losses that were disallowed. The thing is, my actual portfolio is DOWN for the year. I definitely didn't make any real money - I'm sitting on paper losses. But my 1099-B from the broker is showing I have some "realized gains" that I need to pay taxes on because of these wash sales. How is this even possible? I literally have less money than I started with. Do I really have to pay taxes on "phantom gains" when I'm actually at a loss overall? I'm trying to understand if there's anything I can do at this point since it's tax filing season, or if I'm just screwed and need to pay taxes on money I don't actually have. Has anyone dealt with this wash sale nightmare before? Any advice on how to handle this situation? I'm really confused about how to properly report this on my taxes.

Jayden Reed

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This is a common misunderstanding with wash sales. When you have disallowed losses due to wash sales, those losses don't disappear completely - they get added to the cost basis of the replacement shares you purchased. Let me explain: When you sell a stock at a loss and then buy it back within 30 days before or after the sale, that's a wash sale. The IRS doesn't allow you to claim that loss immediately. Instead, the disallowed loss gets added to the cost basis of your replacement shares. So while your 1099-B might show realized gains because some losses were disallowed, those disallowed losses are actually just deferred until you ultimately sell the replacement shares (as long as you don't trigger another wash sale). What you need to determine is whether you still own the replacement shares at year-end. If you sold all positions by December 31st and didn't repurchase within the wash sale window, then all your true economic losses should eventually be reflected.

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Nora Brooks

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But what if you DO still own the replacement shares at the end of the year? Are you just stuck paying taxes on "profits" even though your portfolio is down overall? Also, does this mean I should sell everything by Dec 31 next time to avoid this?

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Jayden Reed

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If you still own the replacement shares at year-end, then yes, you might need to pay taxes on paper gains for that tax year even though your portfolio is down overall. This is because those deferred losses are now built into the cost basis of your current holdings and won't be recognized until you sell those positions (without triggering another wash sale). For future tax planning, selling positions by December 31st can help ensure all your economic activity is captured in one tax year, but be careful not to make investment decisions solely for tax purposes. Sometimes it makes more sense to hold a position based on your investment thesis rather than selling just to recognize a tax loss.

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Eli Wang

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Hey there! I went through almost the exact same situation last year. I was day trading and ended up with about $45,000 in wash sale disallowed losses while my actual portfolio was down like $15,000. It was maddening! I found this really helpful tax analysis tool called taxr.ai (https://taxr.ai) that helped me understand my situation better. It basically analyzed all my trading activity and showed me which specific trades triggered the wash sales and how the disallowed losses affected my tax situation. The tool helped me realize I still had a bunch of replacement shares with adjusted cost basis at year end. Once I understood how the mechanics worked, I was able to properly report everything on my Schedule D and Form 8949.

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Does this tool connect directly to your brokerage account? My trading data is a mess and I have hundreds of transactions. Really don't want to manually input everything.

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I'm skeptical of any service claiming to help with this. Wash sales are complicated and my accountant charges me $500 just to sort through this stuff. How accurate is it really and can it handle complex situations with multiple brokerages?

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Eli Wang

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The tool can import your trading history directly from most major brokerages, so no manual entry needed. You just upload your 1099-B or trading history export and it does the rest. Saved me hours of spreadsheet work. The accuracy has been solid in my experience. It handles complex situations including multiple brokerages and even crypto transactions. It specifically flagged all my wash sales across different accounts that my broker's reporting had missed. My accountant was actually impressed with how detailed the analysis was.

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Alright, I need to follow up on my skeptical comment. I actually tried taxr.ai after posting and I'm legitimately surprised. It correctly identified several wash sales that happened across my two different brokerage accounts that neither broker had caught because they don't talk to each other. The visualization of my trading patterns was eye-opening - I could literally see when I was panic selling and rebuying the same securities. The tax impact analysis showed me exactly why my 1099 was showing gains despite my portfolio being down. For anyone dealing with wash sale headaches, this saved me a ton of confusion. I was able to export everything properly formatted for my tax filing and my accountant said it saved him at least 2 hours of work untangling my mess.

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If you need to talk to the IRS about this situation (which might be a good idea), let me save you some time and frustration. I spent THREE DAYS trying to get through to someone at the IRS about a similar wash sale issue last year. Finally discovered this service called Claimyr (https://claimyr.com) that got me through to an actual IRS agent in about 20 minutes instead of endless hold times. They have a demo video at https://youtu.be/_kiP6q8DX5c that shows how it works. The IRS agent I spoke with was able to explain exactly how to report my wash sales properly and confirmed that yes, sometimes you do have to pay taxes on "phantom gains" in one year even when your portfolio is down overall. At least I got a clear answer instead of stressing for weeks.

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Ethan Scott

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How does this even work? The IRS phone system is notoriously impossible to get through. Is this just paying someone to sit on hold for you?

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Lola Perez

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Yeah right. Nothing gets you through to the IRS faster. They're permanently understaffed and overwhelmed. This sounds like a scam to get desperate people's money during tax season.

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It's not someone sitting on hold for you - it's an automated system that navigates the IRS phone tree and holds your place in line. When an agent finally picks up, you get a call connecting you directly to them. It's basically using technology to beat the phone system. It's definitely not a scam. The service doesn't claim to get you special treatment or move you ahead in line - it just handles the ridiculous wait times so you don't have to keep your phone tied up for hours. You still talk directly to the same IRS agents everyone else does, you just don't waste your day listening to the hold music.

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Lola Perez

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I have to eat my words about Claimyr. After complaining it sounded like a scam, I was desperate enough to try it for my wash sale situation. No joke - I got through to an IRS tax specialist in about 15 minutes after trying unsuccessfully for days on my own. The agent walked me through exactly how to handle reporting my wash sales on Form 8949. She explained that I needed to make sure all my adjustments were properly noted with the correct codes and that my cost basis matched what was on my corrected 1099-B. For what it's worth, she confirmed what others here said - those disallowed wash sale losses aren't gone forever, they're just deferred by being added to the basis of replacement shares. Once I sell those shares (without triggering another wash sale), I'll finally get the tax benefit of those losses.

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Listen, wash sales are the absolute WORST for active traders. I learned this the hard way too. Here's what I do now to avoid this situation: 1. I use the specific identification method for all my trades 2. I track my 30-day windows carefully for any securities I've sold at a loss 3. I consider using different but similar securities (like trading between different ETFs in the same sector) 4. Most importantly - in December I evaluate all my positions and make strategic sales to capture losses where appropriate The key thing to remember is that if you close ALL positions that had wash sales before year-end and don't repurchase within 30 days, you should ultimately get all your economic losses recognized in the current tax year.

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Riya Sharma

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Can you explain a bit more about the "specific identification method"? I just let my broker handle everything and I'm realizing that might be a mistake.

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The specific identification method means you specifically identify which shares you're selling when you have multiple lots of the same security purchased at different times and prices. Instead of using methods like FIFO (first in, first out) or average cost, you choose exactly which shares to sell. Most brokers allow you to select which tax lot you want to sell at the time of the trade. This gives you control over your cost basis and can help manage your tax situation. For example, you might choose to sell your highest cost basis shares for a loss to offset other gains, or sell your lowest cost basis shares if you're in a low tax bracket year.

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Santiago Diaz

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Has anyone considered using a traditional IRA or Roth IRA for active trading instead of a taxable account? I switched to doing most of my active trading in my IRA specifically to avoid wash sale headaches.

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Millie Long

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That's a smart approach, but be careful - wash sales can still apply ACROSS accounts. If you sell at a loss in your taxable account and buy in your IRA within 30 days, the loss in your taxable account can be disallowed. The worst part is you never get that loss back since the basis adjustment happens in the IRA where it doesn't matter for tax purposes!

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Santiago Diaz

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Thanks for that warning! I didn't realize wash sales could apply between taxable and IRA accounts. That's a really important distinction that could have caused me problems. I'll make sure to coordinate my trading across all accounts to avoid accidentally triggering wash sales.

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Caden Nguyen

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I feel your pain - went through something very similar last year and it's incredibly frustrating to owe taxes when your portfolio is actually down. One thing that helped me understand my situation better was creating a simple spreadsheet tracking all my wash sale adjustments. I listed each disallowed loss and which replacement shares got the basis adjustment. This helped me see exactly where my "missing" losses went and gave me confidence that I'd eventually get them back when I sell those positions. Also, don't panic about owing taxes on phantom gains - while it sucks in the short term, those deferred losses are sitting in your replacement shares' cost basis. As long as you eventually sell those shares without triggering another wash sale, you'll get the tax benefit. The timing just gets shifted around. For this year's filing, make sure you're reporting everything correctly on Form 8949 with the proper wash sale codes. If your broker didn't catch all the wash sales (especially if you trade across multiple accounts), you might need to make additional adjustments. The IRS takes wash sale reporting seriously, so getting it right is important. Hang in there - once you get through this tax year, you can plan better strategies to avoid this mess in the future!

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This is really helpful advice, especially the spreadsheet idea! I'm definitely going to try that to track where all my disallowed losses went. One quick question though - you mentioned that brokers might not catch all wash sales, especially across multiple accounts. How would I even know if my broker missed some? Is there a way to double-check their wash sale calculations, or do I need to manually go through every single trade?

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Logan Chiang

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I went through this exact nightmare two years ago and it nearly gave me a panic attack! Had about $55K in disallowed wash sale losses while my actual portfolio was down around $20K. The "phantom gains" tax bill was brutal. Here's what I learned that might help you: First, double-check that your broker correctly identified ALL wash sales. Mine missed several because I had some trades in a second account with them. Wash sales apply across all your accounts with the same SSN, not just individual accounts. Second, if you're still holding any of those replacement shares from the wash sales, consider whether it makes sense to sell them before year-end (as long as you don't repurchase within 30 days). This would finally allow you to recognize those deferred losses. The most important thing though - keep detailed records of everything. I created a master spreadsheet showing every wash sale, which replacement shares got the basis adjustment, and which ones I still owned. This saved me when I got audited the following year. One last tip: if your situation is really complex, consider getting professional help. I ended up paying a CPA who specializes in trader taxes about $800, but they found an additional $12K in losses I had missed and properly structured everything for the IRS. Sometimes it's worth the investment to get it right. You're not alone in this - wash sales catch a lot of active traders off guard. The silver lining is that those losses aren't gone forever, just deferred. Hang in there!

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Thank you so much for sharing your experience - it's reassuring to know I'm not the only one who's been through this mess! Your point about brokers missing wash sales across accounts is really important. I actually do have positions spread across two different brokerages, so I'm wondering if that could be part of my problem. When you mentioned getting audited the following year, that's terrifying! Was the audit specifically because of the wash sale situation, or was it just bad luck? I'm already stressed about filing correctly this year, and the thought of an audit on top of everything else is making me even more anxious. The idea of selling replacement shares before year-end to recognize the losses is interesting, but I'm worried about making any moves right now without fully understanding the consequences. Did you end up doing that, and if so, how did you decide which positions to sell? I'm definitely considering getting professional help at this point. The $800 you paid sounds worth it if they found an additional $12K in losses! Do you have any advice on finding a CPA who specializes in trader taxes? I don't want to go to just anyone and have them mess this up even worse.

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