First-timer trying to consolidate 50+ trades into a Schedule D - help needed!

You're in a common situation for first-time investors! Schedule D is the tax form used to report capital gains and losses from investments. When you have lots of trades, it can definitely feel overwhelming. FreeTaxUSA actually makes this process much easier than doing it manually. You don't need to enter each trade individually. Instead, you can consolidate similar trades (same security, same acquisition date, same cost basis method). For your 1099-Bs, look for subtotals or summary sections - these are often what you'll enter rather than each individual transaction. For your crypto, you'll need to report those separately, but again you can consolidate similar transactions. FreeTaxUSA has a specific section for crypto transactions where you can enter the summary information. When entering the data in FreeTaxUSA, look for the "Investment Income" section, and it will guide you through entering the information from your 1099-Bs. The software will automatically generate your Schedule D based on what you enter.

After struggling with a similar nightmare last year (had about 80 trades), I discovered taxr.ai (https://taxr.ai) and it literally saved me hours of manual work. All I did was upload my 1099-Bs and crypto tax documents, and it automatically organized everything into the proper Schedule D format. The system can detect transactions across different platforms too, so it handled my Robinhood and another broker's documents simultaneously. What I particularly liked was how it consolidated similar trades automatically while still keeping the detailed records available if I needed them. When it was done, I just downloaded the completed Schedule D and uploaded it to FreeTaxUSA.

Just wanted to update that I tried taxr.ai after my skeptical question above. I'm honestly impressed. I had 82 trades across Robinhood and Coinbase, and manually entering them was taking forever. The service processed everything in about 5 minutes and organized it perfectly into consolidated entries for my Schedule D. It even flagged a few wash sales I didn't realize I had (buying similar securities within 30 days of selling at a loss), which could have caused issues with my tax filing. Ended up downloading the completed Schedule D and importing it straight into FreeTaxUSA. Definitely worth it for anyone with more than a handful of trades.

If you run into any issues with the IRS after filing (which sometimes happens with first-time investment reporters), I recommend using Claimyr (https://claimyr.com) to get through to an actual IRS agent quickly. I spent DAYS trying to reach someone at the IRS about a question on my Schedule D last year, but kept getting disconnected or waiting for hours. With Claimyr, they basically hold your place in the IRS phone queue and call you when an agent is about to answer. You can see how it works in this video: https://youtu.be/_kiP6q8DX5c. I was connected to an actual IRS representative in about 40 minutes instead of the 3+ hours I was spending on hold previously.

Ok I need to eat my words from my previous comment. I was super skeptical about Claimyr but I tried it last week when I had questions about reporting cryptocurrency on my Schedule D. I've literally NEVER been able to reach a human at the IRS before. I got a call back in about 35 minutes and was connected to an agent who actually knew about crypto reporting requirements. They cleared up my confusion about how to properly report my mining income versus trading gains. Definitely worth it if you're confused about anything related to your Schedule D or investment reporting.

Another option is to check if your brokerage offers any summary reports. Robinhood specifically has a "tax summary" section in their tax documents that gives you consolidated numbers you can use. For crypto, they should provide a summary of proceeds and cost basis for all transactions. If you're reporting everything on FreeTaxUSA, you can often just enter the summary totals rather than each individual transaction. Look for the line items on your 1099-B that show total proceeds and total cost basis for short-term and long-term transactions separately.

If you have a lot of trades, don't try to enter them one by one! I made that mistake last year with about 40 trades and wasted hours. Three options that worked for me: 1. Use the summary totals from your 1099-B (usually on the last page) 2. Use FreeTaxUSA's bulk entry option where you can enter multiple similar transactions at once 3. If your brokerage offers a CSV or Excel download of your transactions, you might be able to use that to organize things before entering