How do Cash App Stocks affect my tax return?

Thanks for the info! Quick question - what if I never got a 1099-B form from Cash App? Should I just guess what my gains were or do I need to hunt down that form before filing?

If you haven't received your 1099-B, first check your Cash App account - they often provide them electronically through the app or website under tax documents. You can also contact Cash App support to request a copy if you can't find it. Don't guess at your gains. You need accurate information about each transaction including purchase date, sale date, cost basis, and sale proceeds. Cash App should have all this information available in your account history even if you can't find the actual 1099-B form.

Does it work with other investment platforms too? I've got stuff on Robinhood and Webull that's a complete mess tax-wise.

Sounds interesting but I'm kinda nervous about uploading my financial docs to some random website. How secure is it? Do they store your tax documents?

Yes, it works with all the major investment platforms! I've used it with both Cash App and Robinhood docs, and it handles them perfectly. It recognizes the format automatically and extracts all the data. They use bank-level encryption for all uploads and don't permanently store your documents. They explain on their site that they process your documents temporarily just to analyze them, then the data gets deleted from their servers. I was skeptical at first too but they have really detailed security info on their site.

How exactly does this work? Do they just call and wait on hold for you? I'm confused how a service could get through faster than me calling directly.

This sounds like a scam tbh. No way some random service can magically get you to the front of the line when calling customer service. They probably just take your money and you still wait the same amount of time.

They use a system that navigates phone trees and waits on hold for you. When a real person answers, you get a call connecting you directly to that representative. So you don't have to waste time listening to the hold music and automated messages. It's definitely not a scam. They don't promise to put you at the "front of the line" - they just handle the waiting part so you don't have to sit there with a phone to your ear for hours. I was skeptical too until I tried it. The time savings was absolutely worth it especially when I was desperate to get my tax documents before the filing deadline.

Do you know what the threshold is for Cash App to send a 1099-B? Like if I only made $20 in profits do they still have to send one?

There's no minimum threshold for reporting capital gains on your taxes - you need to report all gains regardless of amount. However, brokers are only required to issue a 1099-B if you had proceeds from stock sales (not necessarily gains). For 2024 taxes, even if you only made $20 in profits, if you sold stocks through Cash App, they should issue you a 1099-B showing those transactions. If your total proceeds (not profits, but total sales amount) were very small, there's a tiny chance they might not issue one, but this is rare and doesn't exempt you from reporting.

They have until February 15th to send 1099-B forms legally, so they're probably just waiting until the deadline. You can usually download them directly from the app though - go to Profile > Documents > Tax Statements instead of waiting for an email.

This is really helpful advice! I'm also new to investing and didn't realize there was a difference between short-term and long-term capital gains tax rates. Since most of my Cash App trades were quick buys and sells (those meme stocks moved fast!), I'm guessing mine will all be short-term. Is there a big difference in the tax rates? And do you know if there's an easy way to see the holding period for each trade in the Cash App transaction history?

Yes, there's a significant difference! Short-term capital gains (assets held less than a year) are taxed at your regular income tax rate, which can be anywhere from 10% to 37% depending on your total income. Long-term capital gains (assets held more than a year) get preferential rates - usually 0%, 15%, or 20% for most people. For Cash App transaction history, you can see the buy and sell dates for each trade in your activity feed. Just go to the Investing tab and look at your transaction history - it should show both the purchase date and sale date for each stock. You can calculate the holding period from there. If you bought on January 15th and sold on January 10th of the next year, that's less than a year so it would be short-term. Since you mentioned quick meme stock trades, you're probably right that most will be short-term gains taxed at your regular rate!

This is super helpful, thank you! I'm definitely feeling less anxious about the whole thing now. Quick question about the cost basis errors you mentioned - how would I know if something looks wrong on the 1099-B? Like what should I be looking for specifically? I did do a lot of buying and selling of the same stocks (especially GameStop and AMC) so I'm worried the calculations might be messed up.

Great question! With frequent trading of the same stocks like GameStop and AMC, you definitely want to watch out for potential cost basis errors. Here's what to look for on your 1099-B: 1. **Wash sale adjustments** - If you sold a stock at a loss and bought it back within 30 days, the IRS considers this a "wash sale" and you can't claim the loss immediately. Your 1099-B should show these adjustments, but sometimes brokers miss them. 2. **FIFO vs actual method** - Cash App typically uses FIFO (first in, first out) to calculate which shares you sold, but if you made specific lot selections, make sure that's reflected correctly. 3. **Missing transactions** - Compare your 1099-B against your actual transaction history in the app to make sure every buy and sell is accounted for. The easiest way to check is to pull up your Cash App transaction history and cross-reference it with what's on the 1099-B. If you see big discrepancies in the proceeds or cost basis amounts, that's when you'd want to dig deeper. Most small differences are normal, but if something is off by hundreds of dollars, definitely investigate!

This is really solid advice, especially about the quarterly payments! I hadn't even thought about that part. Quick question - do you know what the threshold is for needing to make quarterly payments? Like if I make similar gains next year (around $800-1000), would that trigger the quarterly payment requirement? I'm trying to figure out if this is something I need to worry about or if it's only for people making much bigger gains. Also love the spreadsheet idea. I've been pretty lazy about tracking my trades but you're right that having my own backup records would probably save me headaches down the road.

Good question! The quarterly payment requirement generally kicks in if you expect to owe $1,000 or more in taxes when you file your return. With gains around $800-1000, you probably wouldn't hit that threshold unless you're in a higher tax bracket or have other income sources. Here's the basic rule: if you expect to owe less than $1,000 in total tax (after withholding and credits), OR if you've paid at least 90% of this year's tax liability through withholding/previous payments, you typically won't face underpayment penalties. Since you mentioned you're a W-2 retail employee, your regular job probably withholds enough to cover most of your tax liability. The extra tax on $1,000 in short-term capital gains might only be $120-220 depending on your bracket, so your regular payroll withholding would likely cover it. That said, definitely worth running the numbers or asking a tax pro if your trading activity increases significantly. Better to be safe than get hit with penalties later!