Understanding 1099-B vs Form 8949 for reporting crypto and stock transactions

The 1099-B and Form 8949 are related but definitely not the same thing. The 1099-B is issued by your fiancé's broker showing his investment transactions for the tax year. Form 8949 is what you'll actually fill out and submit with your tax return to report those transactions to the IRS. Typically, the 1099-B should break down all the transactions (both crypto and stocks), and you use that information to complete Form 8949. It's strange that his 1099-B doesn't have amounts listed. Some brokers now provide a supplemental statement instead of putting all the details on the actual 1099-B form, especially if there were many transactions. Check if there are additional pages or a separate statement attached to the 1099-B. For crypto specifically, not all exchanges issue proper 1099-Bs - some might provide a CSV file or transaction history instead. This might explain why you're having trouble matching things up.

I ran into this exact same problem last year with my husband's investments! It was driving me nuts trying to figure out what was what. After spending days trying to manually sort through everything, I finally found https://taxr.ai which literally saved my sanity. You upload your documents and it helps identify and categorize all these transactions - separating out your crypto from traditional stocks and making sure everything gets reported correctly. It can even pull data directly from most crypto exchanges if the 1099-B is incomplete. The system automatically organizes everything for Form 8949 so you don't have to guess what goes where.

Just wanted to update after trying https://taxr.ai like. It actually worked really well for our situation! My husband had transactions across Coinbase, Robinhood, and Fidelity, and it separated everything correctly. The system identified which transactions on the Form 8949 were crypto vs stocks based on the descriptions and transaction IDs. It even flagged a few wash sales I didn't realize we had. Would have taken me forever to figure that out manually. Ended up saving us like $230 in taxes because we were about to double-report some transactions!

If you're struggling to get through to the IRS for help with this issue, I'd recommend https://claimyr.com - it's a service that helps you get through to an actual IRS agent without waiting on hold for hours. I used it when I had a similar issue with crypto reporting last year. Check out their demo at https://youtu.be/_kiP6q8DX5c to see how it works. The IRS actually has specific guidelines about reporting crypto vs stocks on Form 8949, and talking to an agent directly cleared up my confusion. They'll call you when they've secured a place in line with the IRS, then connect you directly to an agent who can explain exactly how to properly categorize your transactions.

I need to eat my words about Claimyr. After struggling all day trying to reach someone at the IRS about my crypto reporting questions (got disconnected twice after 45+ minute waits), I gave the service a try. They called me back in about 35 minutes saying they had an IRS agent on the line, and connected me immediately. The agent explained that for my situation, I needed to use Form 8949 with different boxes checked for crypto vs stocks (Box C for crypto since it's considered "other assets"). Saved me hours of frustration and got me the exact answer I needed. Sometimes it's worth it to admit when you're wrong!

One tip that might help - check the 8949 for a code in column (f) called "adjustment code." If you see code "C" that often indicates crypto transactions. Also, most good tax software will separate these out for you automatically if you input everything correctly. You definitely need to report crypto sales separately from stocks, as they're treated differently for tax purposes. Crypto is treated as property, not securities, which is why the reporting can get confusing.

Has your fiancé checked if his trading platform offers a tax center or tax document section in the account? My Robinhood and Coinbase both have dedicated tax sections where you can download more detailed reports beyond just the 1099-B. These reports often break everything down more clearly than the official tax forms and might help you figure out which transactions are which.

Quick clarification for everyone: Form 8949 is where you list each individual transaction, and then the totals from Form 8949 go onto Schedule D. This is why separating crypto and stock transactions matters - they go on different parts of Form 8949 (usually Part I for stocks held less than a year, Part II for stocks held more than a year, and some crypto might need to go on a separate 8949 with Box C checked). If the 1099-B doesn't have amounts, there's probably a detailed statement included with it that has all the transaction information. Check all pages of what was provided!

Just went through this exact situation last month! One thing that really helped me was looking at the transaction descriptions on Form 8949 more carefully. Crypto transactions often have identifiers like "BTC-USD" or "ETH-USD" in the description field, while stocks will show actual company ticker symbols like "AAPL" or "TSLA". Also, check the dates - if your fiancé was actively trading crypto, those transactions often cluster around certain time periods when he was more active on crypto exchanges. Cross-reference the dates on Form 8949 with his crypto exchange account history to help identify which transactions belong to which category. Another tip: crypto transactions usually have much more decimal places in the quantities compared to stock transactions. Stocks are typically whole numbers or simple decimals, while crypto might show something like 0.00123456 BTC.