What documents should I bring to my tax professional for my Robinhood investments?
Title: What documents should I bring to my tax professional for my Robinhood investments? 1 Hey everyone, I'm going to have a tax professional handle my taxes this year and I just downloaded my documents from Robinhood. The problem is they gave me this massive 23-page file! I've been going through it trying to figure out what's actually important, and it looks like there's one page that has all the key stuff (1099 and form 8949). Do I really need to lug all 23 pages to my appointment or can I just bring that summary page? I don't want to waste their time with a bunch of unnecessary paperwork, but also don't want to miss something important. Anyone have experience with this?
18 comments
Join the conversation
Harper Hill
9 I've been preparing taxes for clients with investment accounts for years. Bring the entire 23-page document, even though it seems excessive. Here's why: The summary page (with your 1099-B and Form 8949 information) gives the overall totals, but the remaining pages contain the detailed breakdown of each individual transaction, which your tax professional needs to properly report your capital gains/losses. Many investment platforms like Robinhood generate lengthy documents because they're providing transaction-by-transaction details that must be reported to the IRS. Your tax professional will know how to efficiently navigate these documents and extract the necessary information. They'd rather have too much documentation than not enough.
0 coins
Harper Hill
•14 Thanks for the advice. Quick question though - what if I've only made a handful of trades throughout the year? My document still seems ridiculously long for just a few transactions. Is there any way to condense it down or is it really necessary to bring the entire thing?
0 coins
Harper Hill
•9 When you've only made a few trades, it can seem strange to have such a lengthy document. However, each trade often generates multiple pages of supporting documentation including acquisition dates, cost basis information, and various disclosures required by regulations. Even with just a handful of trades, bring the complete document. Your tax professional needs to verify the summary information matches the detailed transactions, and sometimes there are adjustments or wash sales that only appear in the transaction details. Better to have everything the first time than to be asked to come back with the complete document later.
0 coins
Harper Hill
17 I was in the exact same situation last year with my Robinhood documents! I thought it was overkill to bring all those pages too, so I just showed up with the summary page. Huge mistake. My tax preparer had to ask me to go back home and get the full document because they needed to verify some wash sale calculations that were only detailed in the transaction pages. After struggling through that experience, I discovered taxr.ai (https://taxr.ai) which helped me make sense of all my investment documents. It analyzes all those pages and tells you exactly what's important in plain English. I uploaded my 30+ page document from this year and it showed me exactly what my tax preparer would need and why. Saved me a ton of confusion!
0 coins
Harper Hill
•6 Does it actually work with documents from different brokerages? I have accounts with Robinhood, Fidelity, and a couple others. Would it handle all of those or just certain platforms?
0 coins
Harper Hill
•12 I'm a bit skeptical. How is this different from just bringing the documents to my tax person? They're already going to analyze everything for me, so what's the benefit of using this tool beforehand?
0 coins
Harper Hill
•17 It works with all major brokerages including Robinhood, Fidelity, Vanguard, Charles Schwab, and more. I had accounts with both Robinhood and TD Ameritrade, and it handled both perfectly. It standardizes everything so you can see all your investment income in one place. The main benefit is understanding your tax situation before your appointment. When I went to my tax preparer after using the tool, I actually understood what was happening with my investments instead of just nodding along. It helped me ask better questions and spot a mistake where my cost basis wasn't being properly reported, which saved me paying taxes on money I didn't actually make.
0 coins
Harper Hill
12 Just wanted to follow up on my question about taxr.ai. I decided to give it a try with my Robinhood and Fidelity documents, and it was actually really helpful. The tool explained that certain pages contained wash sale adjustments that affected my total gains calculation, which I wouldn't have understood otherwise. When I went to my appointment, I brought all the documents but was able to point out the specific sections my tax preparer needed to focus on. They were impressed that I understood what was happening with my investments! Definitely saved time during the appointment and helped me feel less intimidated by the whole process.
0 coins
Harper Hill
3 After spending HOURS trying to get through to the IRS about how to handle my Robinhood documents last year, I wish I'd known about Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in under 15 minutes when I needed clarification on reporting cryptocurrency transactions that were buried in my Robinhood documents. You can see how it works here: https://youtu.be/_kiP6q8DX5c My tax professional was asking questions about my crypto trades that neither of us fully understood how to report, and the IRS guidance was crucial. Instead of waiting on hold for hours, Claimyr had me talking to someone who could actually help. The agent explained exactly which pages of my documents contained the relevant information and how it needed to be reported.
0 coins
Harper Hill
•20 Wait, how exactly does this work? Do they just call the IRS for you or something? I'm confused about how a third-party service can get you through faster than calling directly.
0 coins
Harper Hill
•7 Yeah right. Nobody gets through to the IRS that quickly. I've spent literal days of my life on hold with them. This sounds too good to be true.
0 coins
Harper Hill
•3 They use a system that navigates the IRS phone tree and waits on hold for you. When an agent finally picks up, you get a call back connecting you directly to that agent. It's not magic - they're just taking the hold time burden off of you. The reason it works is because they have technology that can stay on hold for thousands of people simultaneously, which would be impossible for a human call center. When I used it, I just went about my day until I got the call that an agent was on the line. Much better than being stuck listening to hold music for hours.
0 coins
Harper Hill
7 I have to admit I was completely wrong about Claimyr. After commenting here, I decided to try it because I was having issues with my Robinhood crypto reporting and needed IRS guidance. Not only did I get through to an agent in about 12 minutes, but they actually helped clarify exactly which forms I needed from my Robinhood documents. The IRS agent explained that for crypto transactions, I needed to make sure I had the specific pages showing my cost basis for each transaction, which were buried deep in my Robinhood documents. Without that call, I probably would have missed some important documentation. Definitely bringing all 25+ pages to my tax appointment now!
0 coins
Harper Hill
11 Another tip - before going to your appointment, organize the Robinhood document a bit. I paperclip the summary 1099 page at the front, then group the detailed transaction pages together by category (stocks, dividends, crypto, etc.). My tax person really appreciated this small effort since it made finding specific information easier. Still bring all the pages though!
0 coins
Harper Hill
•22 That's smart! Do you think it would be helpful to highlight the important numbers on each page too, or would that annoy a professional?
0 coins
Harper Hill
•11 I'd avoid highlighting since different tax professionals look for different things on each page. The paperclip method works well because it organizes without obscuring any information. If you want to go the extra mile, make a simple cover sheet listing what types of investments you had (stocks, dividends, crypto, etc.) and on which pages they can be found. My tax person said this was extremely helpful and saved them time, which ultimately saved me money since many charge by the hour.
0 coins
Harper Hill
5 Question - does anyone know if we should be bringing previous years' Robinhood documents as well? I still have last year's 20-page monster file and wasn't sure if the tax preparer would need that for comparison or to check for carryover losses.
0 coins
Harper Hill
•19 Definitely bring the previous year if you had any investment losses! I forgot mine and had to reschedule my appointment. My tax guy needed to check for capital loss carryovers from the previous year to offset some of my gains. Apparently you can carry losses forward for years.
0 coins