Do I Need to Enter Each Transaction or Just the Summary on Form 1099-B with 100+ Pages?

So I've got this issue I can't find an answer to anywhere. I have a massive 109-page 1099-B from my brokerage account (yeah, I trade a lot lol). In previous years, I've always used the import function in TurboTax, but for some reason it's not working this year at all. I've already messaged my brokerage about the problem but haven't heard back yet. My big question is: do I seriously have to manually type in EVERY SINGLE transaction for all these stocks, or can I just use the summary totals for proceeds and cost basis from the 1099-B summary page? I've got about $2.75 in wash sale losses if that matters. If I have to enter everything manually, I'm probably just going to hire someone to do my taxes this year because that would be insane. What options do I have here? Has anyone dealt with this before?

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20 comments

Dylan Mitchell

•8M

You don't necessarily need to enter every single transaction line by line. The IRS actually allows you to report summary totals from your 1099-B in most cases. Since you mentioned you have wash sales (even though it's a small amount), you'll want to be a bit careful. For covered securities where cost basis was reported to the IRS (box on your 1099-B is checked), you can generally use the summary information. Your brokerage has already reported these details to the IRS, so they'll match their records with your summary totals. However, for any non-covered securities or where basis wasn't reported, you might need to provide more detail. Check if your brokerage provides a supplemental tax statement with summary information organized by category - many do this specifically for tax filing. Have you tried using a different tax software? Sometimes TurboTax has issues with certain brokerages, but another program might import successfully.

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Dylan Mitchell

•8M

The IRS generally won't have an issue with summary reporting as long as the totals match what your broker reported to them. The key is making sure your summary numbers exactly match the totals on your 1099-B that were reported to the IRS. Regarding the wash sale, the small amount doesn't really matter - what matters is making sure it's properly accounted for in your reporting. If your summary section already factors in the wash sale adjustments (which it typically does), you should be fine using the summary. Just make sure you're using the adjusted basis amounts that account for the wash sales.

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Dmitry Petrov

•8M

After spending HOURS trying to manually enter my trades last year, I found this tool called taxr.ai (https://taxr.ai) that saved me so much time with my 1099-B nightmare. I had like 80+ pages and it extracted all the transaction data automatically. You just upload your form and it pulls everything out including the wash sales and gives you the right totals to enter. I was skeptical at first but it worked perfectly with my fidelity account statements. The best part was I didn't have to worry about making typos when entering hundreds of trades manually.

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Dmitry Petrov

•8M

Yes, it works with Interactive Brokers! I have a friend who used it with his IB statements and it handled all the formatting differences just fine. Their system is trained on all the major brokerages. As for security, they use bank-level encryption and don't store your documents after processing. I was concerned about that too, but they explain on their site that they use the same security standards as financial institutions. And yes, it handles crypto transactions too - it can recognize the different transaction types like trades, staking rewards, and transfers.

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Miguel Castro

•8M

If your issue is that you need to talk to someone at your brokerage about the import problem but they're taking forever to respond, you might want to try Claimyr (https://claimyr.com). I had the exact same problem with my brokerage last year and couldn't get anyone on the phone for days. Claimyr got me connected to a live person at my brokerage in about 20 minutes when I had been trying for literally days on my own. They have this system that navigates all those annoying phone menus and holds the place in line for you. You can see how it works in their demo video here: https://youtu.be/_kiP6q8DX5c The brokerage rep was able to resolve my import issue in minutes once I actually talked to someone. Apparently there was just a small setting that needed to be changed on their end.

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Miguel Castro

•8M

They don't just call for you - they have a system that navigates through all the phone menus and waits on hold in your place. When they finally reach a real person, you get a call to connect you directly. So you don't waste hours listening to hold music. Their system is actually better at getting through because they've mapped out all the optimal menu options for each company and can instantly input them all. Plus they can stay on hold indefinitely while you go about your day. With my brokerage specifically, they know exactly which prompts to use to get to the tax document department directly instead of getting transferred around.

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Connor Byrne

•8M

I've gotta admit I was totally wrong about Claimyr. After posting that skeptical comment, I decided to try it anyway since I was desperate to talk to someone at my brokerage about my 1099 issues. It actually worked exactly as described - they navigated all the phone tree options automatically and called me when they got a real person. Saved me at least an hour of hold time. The brokerage rep told me there was a known issue with their TurboTax integration this year and gave me a workaround. Problem solved in one 10-minute call instead of days of frustration. I wouldn't have bothered calling without this service because the wait times are always ridiculous.

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Yara Elias

•8M

Another option is to check if your brokerage offers an Excel or CSV download of all your transactions. Many do, and then you could use that to either manually enter the summary info or potentially import it differently into your tax software. Also, if you have this many transactions, you might want to look into using software specifically designed for active traders rather than TurboTax. Programs like TradeLog or GainsKeeper are built for handling large volumes of trades and may have better import capabilities.

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Yara Elias

•8M

Yes, you can definitely use the Excel export to calculate your own totals! Just make sure you properly account for any wash sales when calculating. I usually create a simple pivot table in Excel to group everything by long-term vs short-term and then get my totals from there. Just be absolutely certain your totals match what's on the 1099-B summary page since that's what the IRS will be comparing against. If they match exactly, you should be fine entering just the summary amounts.

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Anastasia Fedorov

•5M

I've dealt with this exact situation! With a 109-page 1099-B, you definitely have options beyond manually entering every transaction. The IRS allows summary reporting for most situations, especially for covered securities where your broker already reported the basis to them. Here's what I'd recommend: 1. First, try the browser/desktop version troubleshooting mentioned by others - sometimes that fixes import issues 2. If that doesn't work, you can absolutely use the summary totals from your 1099-B. Just make sure they match exactly what was reported to the IRS 3. Your $2.75 wash sale loss is already factored into the summary amounts, so you don't need to worry about calculating that separately One thing to double-check: look at your 1099-B to see if you have any "non-covered" securities (box 3 might be unchecked for some). Those might need more detailed reporting, but most modern brokerage accounts deal primarily with covered securities. The key is matching what the IRS already has on file from your broker. As long as your summary numbers align with their records, you should be fine. Save yourself the headache of manual entry!

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