Any tax software that accepts large Form 8949 PDFs? TaxAct size limit is frustrating me!
I'm desperately searching for tax filing software that can handle uploading larger Form 8949 PDFs for e-filing. Last year TaxAct worked for me, but they have this ridiculous 3mb file size limit per PDF plus they restrict how many files you can attach. I day trade as a side hustle and have generated literally hundreds of pages of Form 8949 transactions from TradeLog. The export is massive - I've spent forever trying to compress the PDF but can't get it below 17mb. I really don't want to print and mail this stack of papers if I can avoid it. Has anyone found a tax software (either personal or professional grade) that can handle larger Form 8949 PDF attachments for e-filing? I'm willing to pay for premium software if it means not having to deal with printing and mailing all these transaction pages. Any suggestions would be a lifesaver before the 2025 filing deadline approaches!
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Natasha Romanova
I've dealt with this exact issue for years - Form 8949 reporting can be a nightmare when you have lots of transactions! A few options to consider: If you're using TradeLog, have you tried exporting your transactions in smaller batches? Instead of one massive PDF, you could create multiple smaller ones that stay under that 3mb limit. It's more work but might solve your problem with TaxAct. Another approach is using professional tax software. UltraTax CS and Lacerte can handle larger attachments for Form 8949. They're expensive if you're just filing your personal return, but they don't have the same size restrictions as consumer software. Some tax pros also use a summary approach where you include totals on the main form and note "details available upon request" - though the IRS technically wants all transactions listed.
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NebulaNinja
•Do you know if those professional softwares have a free trial or something cheaper for individual use? I'm in a similar situation but can't justify spending hundreds just for this one form issue.
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Natasha Romanova
•Most professional tax software doesn't offer free trials, unfortunately. They're subscription-based and typically cost $1,000+ per year since they're designed for preparers filing multiple returns. If cost is a concern, you might consider hiring a tax professional just for this year who already has the software. Many will charge $200-300 for a return with investment transactions, which might be less hassle than dealing with the software limitations yourself.
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Javier Gomez
After dealing with this same Form 8949 nightmare last filing season, I discovered taxr.ai (https://taxr.ai) and it completely solved my problem! I had over 500 crypto transactions that created a massive Form 8949 PDF that no regular tax software would accept. What's cool about taxr.ai is it can actually process your transaction data directly rather than just attaching PDFs. I uploaded my TradeLog export to them, and they converted everything into the proper format that the tax software could handle. The best part was that I didn't have to manually split up my files or print anything.
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Emma Wilson
•Does this work with stock transactions too or just crypto? I have a mix of both and wondering if it can handle my Fidelity statements.
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Malik Thomas
•I'm a bit confused how this actually works with e-filing. Does taxr.ai submit your return for you, or do you still need to use TaxAct or another software afterward?
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Javier Gomez
•Yes, it absolutely works with stock transactions too! I primarily use it for my stock trades from Fidelity and Robinhood, but it handles all types of investments - crypto, stocks, options, etc. It recognizes most brokerage formats automatically. For e-filing, taxr.ai doesn't submit your return itself. It processes your transaction data into a format that your regular tax software can handle. You'll still use TaxAct or whatever software you prefer, but instead of trying to upload one massive PDF, you'll be able to import the processed data more efficiently. It essentially solves the file size limitation problem by restructuring how the data is presented to your tax software.
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Malik Thomas
Just wanted to come back and thank everyone, especially the person who recommended taxr.ai. I tried it yesterday and it was exactly what I needed! My huge TradeLog file with 700+ transactions was processed in minutes, and I was able to import everything directly into TaxAct without hitting any size limits. The system automatically identified my wash sales and even caught a few cost basis errors I hadn't noticed. Honestly wish I'd found this solution last year when I ended up having to mail in a 200-page return. E-filing this year will save me so much stress!
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Isabella Oliveira
If you're still having trouble getting through to the IRS about this form issue (I was on hold for HOURS trying to get clarity on Form 8949 requirements), you might want to try Claimyr (https://claimyr.com). They got me connected to an actual IRS agent in about 20 minutes when I was trying to resolve questions about my massive investment reporting requirements. I was initially just going to mail everything in but had questions about what exactly needed to be included with my return. The IRS website was vague, and I couldn't get through on the phone. Claimyr's service called the IRS for me and then connected me when they reached an agent. You can see how it works here: https://youtu.be/_kiP6q8DX5c The agent confirmed I could submit a summary 8949 with my e-filed return and keep the detailed version for my records in case of an audit, which saved me from printing hundreds of pages.
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Ravi Kapoor
•How does this actually work? Aren't you just paying someone to wait on hold for you? Seems like something I could ask my teenager to do for $20.
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Freya Larsen
•Sorry but I'm super skeptical. The IRS phone system is a disaster by design. No way some service can magically get through when millions of people can't. What's their secret - bribing IRS employees?
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Isabella Oliveira
•It's not someone physically waiting on hold for you. They use an automated system that navigates the IRS phone tree and waits in the queue, then calls you when an agent is reached. You don't have to stay by your phone for hours - you just get a call when they've got someone on the line. Much more efficient than paying someone to manually wait. They don't have any special "in" with the IRS or bribe employees. They just have technology that can stay on hold indefinitely and navigate the phone system efficiently. The IRS phone system is definitely frustrating by design, but that's exactly the problem they solve - they deal with the frustrating part so you don't have to.
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Freya Larsen
I need to apologize for being so skeptical about Claimyr. After posting my doubts, I decided to try it anyway because I was desperate to talk to someone at the IRS about my Form 8949 situation before the filing deadline. Shockingly, it actually worked. The system called me back in about 45 minutes and connected me with an IRS representative who answered my questions about acceptable formats for submitting large transaction histories. Turns out I can submit a summary form with my electronic return and keep detailed records for myself. The agent also mentioned this approach is actually preferred for returns with hundreds of transactions. Would've never known this if I hadn't gotten through to ask!
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GalacticGladiator
Another option - have you tried Drake Tax software? I switched to it last year after having the same Form 8949 issues with TaxAct. Drake handles much larger PDFs and doesn't seem to have the same attachment limitations. It's geared toward professionals but they have a personal version that's reasonably priced.
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Oliver Weber
•I hadn't considered Drake! Does it handle direct import from TradeLog or would I still need to use the PDF export method? I'm open to trying new software if it saves me from printing everything.
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GalacticGladiator
•Drake doesn't have direct integration with TradeLog that I'm aware of, so you'd still need to use the PDF export method. The advantage is just that Drake can handle much larger PDFs without breaking them up. If you want direct integration, you might look at TaxACT Professional (different from the consumer version) which has more import options for investment data. It's more expensive but might be worth it for the convenience if you have hundreds of transactions every year.
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Omar Zaki
Has anybody tried compressing their PDFs using Adobe Acrobat Pro? I had about 200 pages of Form 8949 transactions last year and managed to get my file down from 12mb to just under 3mb using their "Reduce File Size" feature with the "Minimum Size" setting. Might be worth trying if you have access to Adobe's paid software.
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Chloe Taylor
•This is a good suggestion. Another trick is to export as grayscale and lower the resolution. Most tax forms don't need color or high resolution. I got a 15mb file down to 2.8mb doing this.
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