Why do I need to mail my stock broker's 1099-B and Form 8949 to the IRS when I already filed electronically via TurboTax?
So I day trade stock options and just received my 1099-B from my broker (processed by APEX Clearing) and it's a MONSTER - over 900 freaking pages! I use TurboTax Premier download version and when I tried to electronically upload the 1099-B, TurboTax basically laughed at me and said it was too large. I ended up just manually entering the summary information into TurboTax and submitted my return electronically. The IRS accepted it right away, so I thought I was good. But then TurboTax tells me I still need to print out and physically mail my entire 900+ page 1099-B to the IRS office in Texas, along with Form 8949 and Form 8453 transmittal. I've been checking shipping rates with USPS, FedEx and UPS because this thing is huge. USPS medium flat-rate priority seems like the best option for this paper monster. But I'm confused - if my electronic return was already accepted, why do I need to send all this extra paperwork? Isn't the whole point of e-filing to avoid sending paper? Has anyone dealt with this before? Is there any way around sending this giant stack of papers?
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Ava Garcia
When you e-file but have a large transaction list like yours, the IRS still needs the detailed records, even though they accepted the summary data electronically. This is because while your e-filed return contains the summary totals, the IRS may need to verify individual transactions during a review or audit. The Form 8453 is specifically designed as a transmittal document for supporting information that can't be included in your electronic filing. Form 8949 is required when you have capital gains/losses from securities transactions. Since your 1099-B is too large to transmit electronically through TurboTax, you need to send the paper documentation. I would definitely use tracking when you ship it, and keep proof of mailing. Also make copies of everything for your records before sending it in. Despite the inconvenience, it's important to comply with this requirement to avoid potential issues later.
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StarSailor}
•Does the IRS actually go through all 900 pages though? Seems like a waste of resources. And how long should we keep copies of these massive documents? My tax files are already taking up a whole cabinet!
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Ava Garcia
•The IRS typically doesn't review every page unless they conduct an audit, but they need access to the complete information if they do decide to verify your transactions. They use automated systems to check much of the data. You should keep copies of all tax documents for at least 3 years from the date you filed, as that's the standard period for the IRS to audit a return. However, if they suspect substantial errors, they can go back 6 years, and there's no time limit for fraudulent returns, so many tax professionals recommend keeping records for 7 years to be safe.
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Miguel Silva
I went through this exact nightmare last year and discovered taxr.ai (https://taxr.ai) after spending hours trying to reconcile my massive 1099-B with what I needed to report. Their system actually handled my 1200+ page document when TurboTax choked on it. It extracted all the transaction data and organized it properly so I could e-file everything without having to mail physical copies. The best part was that it flagged several wash sales I would've missed that saved me from potential IRS questions. I still had to send in a Form 8453, but didn't need to mail the entire 1099-B package since taxr.ai processed it into a format the IRS could accept electronically. Saved me a ton of headache and shipping costs.
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Zainab Ismail
•Sounds interesting but skeptical... How does it work with the IRS requirements? I thought they specifically required mailing physical copies when the transaction list is too large?
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Connor O'Neill
•Does it work with other tax software besides TurboTax? I use H&R Block online and have similar issues with my trading documents.
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Miguel Silva
•It works by processing your 1099-B and creating a proper electronic file format that meets IRS requirements. The IRS actually prefers electronic data when possible - they just need a complete record in a format they can process. What they don't want is just summary data without the supporting transactions. Yes, it works with most major tax software including H&R Block, TaxAct, and FreeTaxUSA. It creates standardized outputs that you can import directly. I switched from TurboTax to H&R Block this year and was still able to use the processed data without issues.
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Connor O'Neill
Just wanted to follow up - I took the plunge and tried taxr.ai after posting here. Honestly wish I'd known about this years ago! Uploaded my 800+ page nightmare from Fidelity and it processed everything in about 20 minutes. The system caught several incorrect cost basis entries my broker had reported and flagged them for me to review. I was able to import everything right into H&R Block and e-file the complete return without having to mail anything physical. The time saved was worth every penny, and knowing I won't have to deal with the potential audit risk of manual entry mistakes gives me serious peace of mind. If you're a frequent trader, definitely check it out!
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Yara Nassar
Another option to consider is Claimyr (https://claimyr.com) for dealing with IRS questions about large trading documents. I had to mail in my massive 1099-B last year and got a notice from the IRS questioning some of my transactions months later. Trying to call the IRS was impossible - kept getting disconnected or waiting for hours. I used Claimyr's service (there's a demo video at https://youtu.be/_kiP6q8DX5c) and they got me connected to an actual IRS agent in about 15 minutes instead of the hours I wasted trying on my own. The agent was able to look up my file and confirm they had received my paperwork but flagged several transactions for review. Saved me weeks of back-and-forth letters.
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Keisha Robinson
•How does this actually work? Is it just connecting you to the regular IRS line or do they have some special access? Seems too good to be true considering how impossible it is to get through.
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GalaxyGuardian
•I call BS on this. Nobody gets through to the IRS in 15 minutes. I've been trying for months to resolve an issue and can never get past the automated system. If this worked, everyone would be using it.
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Yara Nassar
•They use a system that navigates the IRS phone tree and waits on hold for you, then calls you when an actual agent is on the line. It's like having someone wait on hold for you so you don't waste hours of your day. It's the same IRS line everyone else calls, they just have technology that efficiently handles the waiting part. I was skeptical too, but after wasting an entire day trying to get through myself, I gave it a shot. Different experiences may vary, but it worked exactly as advertised for me - took about 15 minutes that day, though I imagine wait times depend on when you call and current IRS volumes.
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GalaxyGuardian
Alright, I need to apologize and follow up. After posting my skeptical comment, I decided to try Claimyr as a last resort for my ongoing IRS issue about missing stock sale documentation. I was honestly shocked when I got a call back with an actual IRS agent on the line in about 25 minutes. The agent was able to pull up my file immediately and confirmed they never received my mailed 1099-B package (even though I had delivery confirmation from USPS!). She gave me a fax number to send the documentation directly and notated my account. Problem solved in one call after months of frustration. Definitely eating my words on this one.
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Paolo Ricci
Just a practical shipping tip - don't use USPS flat rate for this if you care about tracking. I sent my 700+ page 1099-B package last year via flat rate and it got "lost" for weeks. The tracking just stopped updating. Eventually it arrived at the IRS but I was stressing the whole time. FedEx or UPS costs more but their tracking is way more reliable. And definitely keep a scanned copy of everything you send. The peace of mind is worth the extra cost in my opinion.
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Dmitry Popov
•Thanks for the shipping advice! Did you need to include anything special with your package or just the forms and 1099-B? I'm worried about it getting separated from my e-filed return somehow.
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Paolo Ricci
•Make sure Form 8453 is on top as it's the transmittal form that connects your paper documents to your e-filed return. It has your name, SSN, and a special e-file number that links everything together. Also write your SSN at the top of each form (not each page, just each form type) in case pages get separated. I also included a brief cover letter with my name, SSN, tax year, and exactly what was enclosed just to be extra careful. And yes, definitely scan everything before sending - I used a fast scanner app on my phone since there were so many pages.
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Amina Toure
Has anyone actually been audited because of trading activity? I'm in the same boat with hundreds of pages of transactions and wondering if the IRS really looks at this stuff or if it's just a formality.
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Oliver Zimmermann
•Yes, I got audited two years ago specifically for options trading. They questioned several wash sales and some transactions where my reported cost basis didn't match what my broker reported. Had to provide all documentation and ended up owing an additional $3800 plus interest. Don't mess around with this stuff.
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Paolo Moretti
I feel your pain with the massive 1099-B! I'm a day trader too and dealt with this exact situation last year with my broker's 600+ page document. One thing I learned is that you should definitely keep a copy of your certified mail receipt or delivery confirmation - the IRS processing centers can be slow to update their systems, and having proof of delivery saved me when I got a notice months later claiming they never received my documents. Also, make sure you're sending it to the correct IRS processing center address listed in your TurboTax instructions - different states have different mailing addresses for Form 8453 submissions. I initially sent mine to the wrong center and had to resend everything, which was a nightmare. The good news is that once they process it (which can take 6-8 weeks), you shouldn't have any issues as long as your summary data matches what you e-filed. Just budget for the shipping costs as part of your trading expenses - it's deductible!
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Dyllan Nantx
•Great point about the certified mail receipt! I'm definitely going to use that when I send mine in. Quick question - when you say it's deductible as a trading expense, do you mean I can write off the shipping costs on Schedule C or is it somewhere else on the return? I'm still learning all the ins and outs of tax deductions for active trading.
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