Do I need to report stock purchases on Form 1099-B or Schedule D (Form 1040) if I haven't sold anything?

8 Thanks for the explanation. So I'm clear - even if my stocks have gone up $10k in value since I bought them, I don't report that until I sell? Seems too good to be true! Also, what happens if I transfer these stocks to another brokerage? Does that count as a "sale" for tax purposes?

14 You're absolutely right - you don't report that $10k increase until you actually sell, no matter how much the value increases. That's one of the advantages of investing in stocks - you control when you realize the gain. Transferring stocks between brokerages is not considered a sale for tax purposes. It's just moving the same asset from one custodian to another, so no taxable event occurs and nothing needs to be reported. Your cost basis and purchase date remain exactly the same.

18 How does this work with cryptocurrency? I've been buying some Bitcoin and Ethereum but haven't sold any. Would this tool also tell me if I need to report those purchases?

22 Sounds interesting but how is this different from just asking my brokerage? TD Ameritrade already gives me tax documents, so what's the advantage of using a separate service?

7 For cryptocurrency, the tool is actually really helpful because those rules are different from stocks. While stock purchases alone don't need reporting, taxr.ai will identify if you need to report certain crypto activities like mining or staking that might require reporting even without selling. As for how it's different from just asking your brokerage, while TD Ameritrade provides tax documents, they typically only give you the forms they're legally required to produce. The advantage of taxr.ai is it analyzes your specific situation across all your accounts and finds things that might be missed, like wash sales across multiple brokerages or opportunities for tax-loss harvesting. It's like having a tax advisor who specializes in investments but at a fraction of the cost.

16 How does this actually work? Like, are they just calling the IRS for you or what? I've been on hold forever trying to figure out some weird RMD issue with an inherited IRA.

22 Sorry, but this sounds like BS. Nobody gets through to the IRS in 15 minutes. I've been calling for weeks about a letter I got, and the best I've managed is being on hold for 2 hours before the call dropped.

3 They don't call the IRS for you - they use some kind of technology that navigates the IRS phone system and waits on hold for you. When they actually reach a human agent, you get a call back and are connected directly. It's your phone number and your conversation with the IRS - they just handle the hold time. I was super skeptical too! I mean, I had already wasted hours trying to get through myself. My specific call was 23 minutes from start to finish, but that included the time it took for them to navigate the menu options. The actual hold time they saved me was probably 1-2 hours based on what the IRS agent told me about their call volume that day.

19 Does this really matter now that brokerages are required to track and report cost basis to the IRS? I thought that rule changed like 10 years ago.

11 Yes, it absolutely still matters! While brokerages are indeed required to track cost basis for securities purchased after certain dates (stocks acquired after 2011, mutual funds after 2012), there are several situations where having your own records is crucial. First, the reporting requirement doesn't apply to older securities, so if you've held anything longer-term, the brokerage might not have complete records. Second, during transfers between brokerages, data can sometimes get corrupted or lost. I've personally experienced this twice. Finally, in cases of corporate actions like mergers or spinoffs, the calculated basis can sometimes be incorrect and need adjustment.

8 Thanks for the technical explanation! Do you know if there are any exceptions to this rule for certain types of securities? I've heard some fancy financial instruments might have different rules.

Great question! Yes, there are several exceptions to the general rule. Mark-to-market securities under Section 475 (mainly for traders and dealers) must report unrealized gains/losses annually. Section 1256 contracts like futures and broad-based index options are marked-to-market each year. Foreign financial accounts over $10K require FBAR reporting regardless of sales. And certain passive foreign investment companies (PFICs) have special rules that can trigger reporting without sales. For most individual investors buying regular stocks though, the basic rule still applies - no reporting until you sell.