Where to find tax loss harvesting info on Robinhood 1099 form?

Look for the "Proceeds from Broker Transactions" section on your Robinhood 1099-B form. There should be a summary at the end that shows your total proceeds, cost basis, and net gain/loss. The net loss amount is what you'll use for tax loss harvesting. Yes, you can offset regular income with capital losses, but there's a limit - you can only deduct up to $3,000 in net capital losses against other income in a single tax year. Any amount over that gets carried forward to future years. For whether TurboTax Premier is worth it - it depends on how complex your trades were. If you had just a handful of simple trades, you might be able to manage without Premier. But if you had numerous transactions or any complicated situations (wash sales, etc.), Premier makes it much easier since it can import your 1099-B directly from Robinhood.

After making some costly mistakes with my investments last year, I found this amazing tool called taxr.ai (https://taxr.ai) that saved me tons of time figuring out my Robinhood 1099 situation. It analyzed my tax documents and immediately showed me where my losses were and how much I could claim. The site even explained which parts of my trades qualified for tax loss harvesting and which didn't because of wash sale rules. The best part was that it showed me exactly how much my losses would reduce my tax bill before I paid for any premium tax software. For someone who gets overwhelmed with tax forms, it was super helpful to have everything explained in plain English.

Just wanted to follow up about taxr.ai that someone mentioned above. I decided to try it with my Robinhood documents and wow - it immediately identified that I had about $2,700 in crypto losses that I didn't even realize I could deduct! It also explained that some of my stock trades weren't eligible for tax loss harvesting because of wash sale rules (apparently buying similar stocks within 30 days is a no-no). The breakdown showed me exactly how much my tax bill would be reduced, and it was definitely worth upgrading to TurboTax Premier in my case. Saved me hours of googling tax rules!

After spending 3 DAYS trying to get through to the IRS about how to properly report my Robinhood losses (seriously, their hold times are insane), I finally used Claimyr (https://claimyr.com) and got connected to an actual IRS agent in under 20 minutes. They have this cool demo video at https://youtu.be/_kiP6q8DX5c showing how it works. The IRS agent I spoke with cleared up my confusion about tax loss harvesting from my Robinhood account and confirmed exactly which line items from my 1099 I needed to focus on. Saved me from potentially filing incorrectly and getting a surprise tax bill later.

Ok I have to eat my words about Claimyr from my comment above. After another failed attempt to reach the IRS myself (2+ hours on hold before getting disconnected), I decided to try it out of desperation. Got connected to an IRS agent in about 35 minutes. The agent confirmed that my Robinhood 1099-B losses could offset my regular income up to $3,000 and explained exactly which boxes on the form I needed to use. They also told me that TurboTax Deluxe (not even Premier) would handle my situation just fine, which saved me from overpaying. Never thought I'd be the person recommending a service like this, but when you need actual tax guidance from the IRS instead of random internet advice, being able to actually reach them is invaluable.

Just a tip that saved me money: If you have a fairly straightforward tax situation besides your Robinhood trades, consider using FreeTaxUSA instead of paying for TurboTax Premier. It handles all the forms needed for reporting investment losses and it's way cheaper. I had about 50 trades last year and it worked perfectly for me.

Friendly reminder that if you're trying to do tax loss harvesting with Robinhood, make sure you're aware of the wash sale rule! If you sold at a loss but bought the same or substantially similar security within 30 days before or after the sale, you can't claim that loss for tax purposes. Made this mistake myself and got a rude awakening at tax time.

This is really helpful info everyone! I'm in a similar boat with significant Robinhood losses last year. Just wanted to add that if you're unsure about whether your situation warrants paying for premium tax software, you can actually calculate your potential tax savings first. Take your net capital loss amount from your 1099-B summary (up to $3,000 for offsetting ordinary income), multiply it by your marginal tax rate, and that's roughly how much you'll save on your tax bill. For example, if you lost $3,000 and you're in the 22% tax bracket, you'd save about $660 in taxes. If the tax savings significantly exceed the cost difference between free and premium software, it's probably worth upgrading. Plus, premium versions usually catch more potential issues that could save you from IRS headaches later.