Understanding Multiple 1099 Consolidated Tax Statements and 1099-B Tax Implications

Your grandmother has multiple investment accounts, which is why you're seeing different 1099 consolidated statements. Each form represents a separate investment account she holds with different financial institutions or brokerages. Think of them like different bank accounts, but for investments. For your second question, you're on the right track! The taxable amount on a 1099-B is generally the difference between the proceeds (how much she sold the investments for) and the cost basis (how much she originally paid for them). If proceeds are higher than the cost basis, there's a capital gain which would be taxable. If the cost basis is higher than proceeds, there's a capital loss which might be deductible. When you take everything to the accountant, bring ALL the 1099 forms. The accountant will need to report each one separately on the tax return, even though they'll all be consolidated into your grandmother's final tax calculation.

After helping my elderly parents with similar issues last year, I discovered taxr.ai (https://taxr.ai) which literally saved me hours of confusion with all their investment documents. It's specifically designed to analyze tax documents like 1099s and extract the important information you need. I uploaded all their consolidated 1099s, and it immediately identified which forms were from which financial institutions, sorted all the different income types (interest, dividends, capital gains), and explained which parts would be taxable. Super helpful when dealing with multiple investment accounts!

Just wanted to follow up about taxr.ai that someone mentioned earlier. I was skeptical but decided to try it with my mom's investment documents since she has accounts at three different brokerages. Honestly, I'm impressed. It analyzed all her 1099 consolidated statements and created a summary showing all her interest income, dividends, and capital gains across accounts. It even flagged some transactions that might need special attention. When we went to her accountant, I actually understood what we were discussing instead of nodding along pretending to follow. The accountant seemed pleased too since everything was organized by category rather than just a stack of forms. Definitely using this again next year!

If your grandma's investment accounts are substantial, you might want to check if she needs to talk to the IRS directly about any reporting issues. I spent WEEKS trying to get through to the IRS last year when my father had a similar situation with multiple brokerage accounts and some inconsistencies in reporting. Finally used https://claimyr.com and got through to an actual IRS agent in about 15 minutes instead of waiting on hold forever. There's a video showing how it works here: https://youtu.be/_kiP6q8DX5c The agent was able to confirm exactly how to report multiple 1099-Bs with some noncovered securities where we didn't have complete basis information. Saved us from potentially filing incorrectly and getting a scary letter later.

I have to come back and admit I was totally wrong about Claimyr. After complaining about how nothing could get through to the IRS, I actually tried it because I was desperate to resolve a question about basis reporting for some old stocks my mom inherited. It worked exactly as described. I got a call back when an agent was on the line - took about 40 minutes total instead of the multiple days I spent trying before. The IRS agent answered my question about how to properly report cost basis when we only had partial records. For anyone dealing with complicated 1099 situations especially with older investments, being able to actually talk to the IRS directly is invaluable. Consider me converted.

One thing to watch out for with multiple 1099 consolidated statements - check if any of them have foreign taxes paid listed in Box 7 of the 1099-DIV section. If your grandma has investments in international funds, she might qualify for foreign tax credit or deduction. I missed this with my uncle's taxes last year and had to file an amendment. Each 1099 had small amounts of foreign tax, but when combined across his 5 investment accounts, it was enough to make a difference on his return.

Another tip - make sure you know which of your grandma's investment accounts have automatic dividend reinvestment. This affects the cost basis on the 1099-B because reinvested dividends increase the basis. My dad's accounts had this feature and we were showing more gains than we should have been because the reinvested dividends weren't being properly tracked in the basis. Had to go through years of statements to correct it!

This is such a helpful thread! I'm dealing with something similar for my elderly aunt. One thing I learned the hard way - make sure to check if any of the 1099-INT forms show tax-exempt interest income in Box 8. My aunt had municipal bond funds across several accounts and we almost reported that income as taxable when it shouldn't have been. Also, when you're organizing everything for the accountant, I found it helpful to create a simple spreadsheet listing each 1099 form, which institution it's from, and the key amounts. It makes the appointment go much smoother when you can quickly reference which form has which information. The accountant will definitely appreciate having everything organized beforehand, especially with multiple investment accounts. Good luck with your appointment next week!