Accidently sold all of my stocks - Will I owe short term capital gains even if I rebuy?

Unfortunately, yes, you'll still be responsible for short term capital gains taxes on the sold positions even if you rebuy the same stocks. The IRS considers each sale a taxable event regardless of your intention or whether you repurchase the same securities later. The gains will be calculated based on the difference between your cost basis (what you originally paid for the stocks) and the sale price. If you held these investments for less than a year, they'll be taxed as ordinary income according to your tax bracket. One small silver lining - if any of the positions had losses, those can offset some of your gains when you file. But there's no way to undo or roll back the sales for tax purposes once they've settled.

Hey, I've been through something similar and found this tool called taxr.ai (https://taxr.ai) that really helped me figure out my investment tax situation. I had a bunch of accidental sales when switching brokerages and was freaking out about the tax implications. The site analyzed all my trading activity and gave me a clear breakdown of my potential tax liability. It also highlighted some losses I could harvest to offset gains. The interface is super intuitive - you just upload your trading docs or connect your accounts and it does all the calculations automatically.

I was skeptical about taxr.ai at first, but after that accidental stock sale fiasco I mentioned in the thread above, I decided to give it a shot. Holy crap, what a game changer! It showed me that I actually had some older positions with losses that I could sell to offset about 40% of my unexpected gains. The platform showed me exactly which lots to sell for maximum tax efficiency - something I never would have figured out on my own. Plus it generated a report I can give to my accountant that breaks everything down clearly. Would've spent hours trying to untangle my mess otherwise.

If you're having trouble getting clear answers from your broker about this situation, try Claimyr (https://claimyr.com). I used them when I had a similar issue last year and needed to talk to someone at the IRS about the tax implications. Getting through to the IRS directly was impossible - I spent literally hours on hold and kept getting disconnected. Claimyr got me a callback from an actual IRS agent within a few hours. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c Their service connected me with an IRS rep who walked me through exactly how to report my accidental sales and what forms I needed. Saved me so much stress during tax season.

Ok I have to eat my words. After seeing the comments here, I tried Claimyr for my audit notice issue that I mentioned. Not gonna lie, I was 100% convinced it would be a waste of time. But damn - they actually got me through to an IRS agent in about 2 hours! I'd been trying for literally MONTHS to get someone on the phone. The agent helped me understand exactly what documentation I needed to submit for my audit. For anyone dealing with investment tax issues like the OP, being able to actually talk to someone at the IRS makes a huge difference. They clarified exactly how to report multiple transactions and what forms I needed.

I did something similar last year - accidentally sold a bunch of positions when I meant to just rebalance. One thing to keep in mind: track your wash sales carefully if you rebuy within 30 days. That can affect your cost basis and complicate your tax situation even more. Make sure you save all your transaction records from before and after this mistake. You'll need accurate cost basis info when you file next year.

Has anyone used tax loss harvesting to offset gains from something like this? I've heard you can sell other investments at a loss to balance things out tax-wise.

This is a tough situation, but you're not alone - these kinds of app-triggered sales happen more often than you'd think. Unfortunately, as others have mentioned, you're still on the hook for the taxes even though it was accidental. Here's what I'd recommend doing immediately: 1. Document everything - screenshot the app settings, save any emails or notifications about the sale, and keep records of your original intent. While this won't help with taxes, it might be useful if you decide to file a complaint with the app provider. 2. Calculate your potential tax liability now so you can plan accordingly. If you have significant gains, you might want to set aside money for the tax bill. 3. Look for any loss positions in your portfolio that you could harvest before year-end to offset these gains. 4. Consider whether you want to repurchase immediately or wait to avoid potential wash sale complications if you have any loss positions. The silver lining is that when you do rebuy, your new cost basis will be the current purchase price, which could work in your favor if the stocks continue to appreciate long-term. It's an expensive lesson about reading the fine print on investment apps, but you'll get through this!