First timer - How do I go about Consolidating Trades into a Schedule D with tons of transactions?

The good news is that FreeTaxUSA handles this pretty well! Schedule D is just the tax form where you report capital gains and losses from your investments. Here's a simplified explanation: When you have lots of transactions (like your 50-60 trades), you don't need to list each one separately on your tax return. You can consolidate similar transactions into summary lines on Schedule D. This means grouping together trades with the same characteristics - like short-term vs long-term, covered vs non-covered transactions. Your 1099-Bs from Webull and SoFi should indicate which transactions are "covered" (meaning the broker reported the cost basis to the IRS) and "non-covered" (where you're responsible for reporting the correct basis). You'll want to group these separately. FreeTaxUSA will walk you through entering this information section by section. You'll just need to input summary information from your 1099-Bs rather than each individual trade. The dividends will be reported separately on Schedule B and flow to your 1040.

After dealing with a similar situation (I had 70+ trades last year!), I found a tool called taxr.ai that literally saved me hours of headache. The thing about consolidating trades into Schedule D is that you still need to make sure your totals match exactly what's on your 1099-B forms, and manually adding everything up is prone to errors. I uploaded my 1099-Bs to https://taxr.ai and it automatically parsed all the transactions, categorized them correctly (short-term vs long-term), calculated my wash sales properly, and gave me the exact summary figures to put on Schedule D. Then I just entered those totals into FreeTaxUSA instead of trying to reconcile everything manually. The best part was that it caught a discrepancy between what my broker reported and my own records, which saved me from a potential audit trigger. Definitely worth checking out if you're dealing with lots of transactions!

I want to follow up about my experience with taxr.ai since I decided to try it despite my initial skepticism. I'm genuinely impressed. My situation was similar with multiple brokers (Fidelity, Robinhood, and Coinbase) and about 40 trades throughout the year. The tool organized everything clearly and gave me exactly what I needed for Schedule D - it separated short-term from long-term gains, properly handled my wash sales (which I didn't even know I had), and even flagged some transactions that my broker had incorrectly categorized. I was able to enter the consolidated information into FreeTaxUSA in about 15 minutes, whereas I had spent 3 hours the previous day trying to organize everything manually and got nowhere. Just wanted to share since this thread helped me find a solution!

If you're planning to call the IRS for help with Schedule D questions (which I tried to do), save yourself hours of waiting on hold and use Claimyr. After spending literally 3 hours on hold with the IRS trying to get clarification about reporting crypto trades correctly, I found https://claimyr.com and watched their demo at https://youtu.be/_kiP6q8DX5c. The service basically holds your place in the IRS phone queue and calls you when an agent is about to answer. I got through to an actual IRS person who walked me through exactly how to report my consolidated trades on Schedule D. They even explained how to handle the crypto transactions that didn't appear on my 1099-B. Best $20 I've spent during tax season, considering I was about to give up and just guess on my tax return.

I need to apologize and correct myself. After dismissing the Claimyr service as "BS" in my previous comment, I decided to try it myself when I needed to call the IRS about some confusion on my Schedule D reporting. It actually works exactly as described. I went to the website, entered my info, and went about my day. About 2 hours later (which is probably how long I would have been on hold anyway), I got a call telling me an IRS agent was about to connect - and within seconds I was talking to a real person who helped clarify my questions about consolidating crypto trades. I was wrong and I'm genuinely impressed. For anyone dealing with complicated Schedule D issues who needs IRS guidance, this service is legit and saved me from an afternoon of hold music. Thanks to the person who recommended it.

Something that really helped me with Schedule D consolidation was using the "Gain/Loss Report" feature in my brokerage account. Most brokers (including Webull and SoFi) have a tax reporting section where you can download a spreadsheet of all your transactions already categorized by short-term and long-term. I imported this into Excel, created some simple SUM formulas for each category, and then entered those totals into FreeTaxUSA. The key is making sure your totals match EXACTLY what's reported on your 1099-B forms, down to the penny. If they don't match, the IRS computer will flag your return. For the crypto, those are reported slightly differently but the same consolidation concept applies. Just make sure you're keeping them separate from your regular securities.

Don't forget about Form 8949! A lot of new investors miss this. Schedule D is actually a summary form, and Form 8949 is where you list the details. If your 1099-B is complete and accurate (with all cost basis reported to the IRS), you might be able to skip detailed reporting on 8949 and just put the totals directly on Schedule D. But if you have any transactions where the cost basis wasn't reported to the IRS, or if you need to make adjustments to what your broker reported, you'll need to complete Form 8949 as well. FreeTaxUSA should walk you through this, but just be aware of it. For cryptocurrency specifically, most brokers don't report cost basis to the IRS yet, so you'll likely need to report those transactions in a separate section of Form 8949.

As someone who went through this exact nightmare last year with about 80 trades across multiple platforms, I feel your pain! Here's what I wish someone had told me from the start: First, don't panic - FreeTaxUSA really does handle this well once you understand the process. The key thing to remember is that Schedule D is just a summary of your gains and losses, grouped by categories (short-term vs long-term, covered vs non-covered). Here's my step-by-step approach that worked: 1. Download all your 1099-B forms and any supplemental statements from your brokers 2. Separate transactions into the four main buckets: short-term covered, short-term non-covered, long-term covered, long-term non-covered 3. For each bucket, add up total proceeds, total cost basis, and any wash sale adjustments 4. Enter these summary totals into FreeTaxUSA For your crypto transactions, those will likely be in the "non-covered" category since most brokers don't report crypto cost basis to the IRS yet. Make sure to keep those separate from your stock trades. The dividends you mentioned are reported separately on Schedule B, so don't worry about mixing those with your Schedule D calculations. One last tip: double and triple-check that your final totals match exactly what's on your 1099-B forms. Even a penny difference can trigger IRS correspondence later. Take your time - it's better to be accurate than fast!