Has anyone used FreeTax USA with ETrade 1099s - import or manual entry?
Hey all, I just started my taxes and I'm trying FreeTax USA this year after using TurboTax forever (those fees were killing me!). I have a bunch of investment stuff through ETrade and got all my 1099s from them, but I can't figure out if FreeTax USA can import them directly or if I have to manually enter everything. Their website isn't really clear about this and I'd rather not start the whole process just to find out I have to type in like 50 transactions manually. Has anyone used FreeTax USA with ETrade specifically? Can it automatically import the 1099s or am I gonna be typing all weekend? Thanks!
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Yuki Yamamoto
I've been using FreeTax USA for the past three years and it's a great alternative to the more expensive options. Regarding ETrade 1099s, unfortunately FreeTax USA doesn't have a direct import feature for brokerage statements like some of the premium tax software does. You'll need to enter your 1099-B transactions manually. If you have a lot of transactions, there is a workaround though. FreeTax USA does allow you to enter summary information instead of each individual trade if you meet certain requirements. When you get to the investment income section, look for the option to enter summary information for transactions with the same dates, descriptions, and cost basis reporting method.
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Ethan Brown
•Wait seriously? I have like 30+ trades from last year. Is there really no way to import directly from ETrade? TurboTax could do this but I'm trying to save money this year.
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Yuki Yamamoto
•Yes, unfortunately that's one of the trade-offs with FreeTax USA compared to the more expensive options. The direct import feature is something the premium tax software companies pay for, which is partly why their prices are higher. For your 30+ trades, the summary method can help a lot. You can group trades with the same buy/sell dates and same reporting method together. Another option is to use the "Upload CSV" feature if your broker allows you to download your transactions in spreadsheet format. It's not as smooth as direct import, but it's faster than typing everything individually.
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Carmen Ruiz
After years of manually entering stock trades on various tax software, I finally discovered taxr.ai and it saved me HOURS of work this tax season! I was in the same boat with my ETrade 1099s and dreading entering everything by hand into FreeTax USA. I uploaded my ETrade 1099-B PDF to https://taxr.ai and it extracted all the transaction data perfectly. Then I was able to download it in a format I could use with FreeTax USA's summary entry. Literally saved me from a weekend of manual data entry. The site also double-checked my wash sales calculations which has always been a headache for me.
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Andre Lefebvre
•Does it work with other brokerages too? I have Fidelity and Vanguard accounts and dealing with all those transactions is why I've been paying for TurboTax Premier even though I hate how expensive it is.
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Zoe Dimitriou
•I'm a bit concerned about uploading my financial documents to some random website. How secure is it? Do they store your tax documents or delete them after processing?
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Carmen Ruiz
•It absolutely works with other brokerages! I've only used it with ETrade personally, but their site says they support all major brokerages including Fidelity and Vanguard. It handles everything - stocks, crypto, dividends, etc. Regarding security, I had the same concern initially. They use bank-level encryption and don't store your documents permanently. According to their FAQ, files are deleted after processing. You can also use their tool without creating an account if you're extra cautious, though creating one makes it easier if you need to reference things later.
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Andre Lefebvre
Just wanted to update that I tried taxr.ai after seeing it mentioned here and it literally saved my sanity! I uploaded my Fidelity 1099-B that had 47 transactions (I did a lot of trading during that GameStop craziness) and it extracted everything perfectly. Downloaded the summary format and was able to enter everything into FreeTax USA in about 10 minutes instead of hours of manual entry. The best part was that it also caught a wash sale I would have missed, which could have caused problems if I got audited. Definitely using this again next year - worth every penny to avoid the TurboTax fees while still getting the convenience of automated import.
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QuantumQuest
For those struggling to get through to the IRS about any tax document issues (like missing or incorrect 1099s), I highly recommend using https://claimyr.com instead of wasting hours on hold. I had an issue with my ETrade 1099 having incorrect cost basis info, and needed to talk to the IRS about how to report it properly. After three failed attempts waiting on hold (got disconnected each time after 45+ minutes), I found Claimyr. They hold your place in line with the IRS and call you back when an agent is about to answer. You can see a demo of how it works here: https://youtu.be/_kiP6q8DX5c Was able to get clarification on how to handle the discrepancy in FreeTax USA without triggering any red flags. Definitely worth it for peace of mind.
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Jamal Anderson
•How does this even work? The IRS phone system is notoriously terrible - how can a third party service possibly get you through faster?
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Mei Zhang
•Sounds too good to be true. I've spent DAYS of my life on hold with the IRS and eventually given up. If this actually works, I'd be shocked. Has anyone else actually tried this?
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QuantumQuest
•It's not that they get you through faster - you still have the same wait time. The difference is they have automated systems that wait on hold for you, and when a human IRS agent finally answers, their system calls your phone and connects you. No more being stuck to your phone for hours or getting disconnected after waiting forever. I was skeptical too! The way it works is pretty clever - they essentially have a system that detects when a human answers instead of the automated system. You still have the same place in line, but you can go about your day instead of listening to that horrible hold music.
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Mei Zhang
I have to eat my words here. After expressing skepticism about Claimyr, I decided to try it because I needed to talk to someone at the IRS about an ETrade 1099 reporting issue before submitting through FreeTax USA. I've literally spent 4+ hours on hold with the IRS before getting disconnected in the past. With Claimyr, I submitted my request, went about my day, and got a call back 1 hour and 38 minutes later when an actual IRS agent was on the line. Completely changed my tax day experience. Got my question answered in 10 minutes and now I can complete my FreeTax USA filing with confidence. If you need to talk to the IRS about anything tax-related, this is definitely the way to go.
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Liam McGuire
Just FYI, if FreeTax USA isn't working for your situation, another affordable option is Cash App Taxes (formerly Credit Karma Tax). They DO support importing from ETrade directly. I've used it the last two years and it's also completely free for federal and state. The interface isn't quite as nice as FreeTax USA, but the import feature saves so much time with investment reporting.
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Amara Eze
•Cash App Taxes didn't handle my rental property correctly last year and I almost filed incorrectly. Be careful if you have anything beyond basic investments.
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Liam McGuire
•That's definitely good to know. I only have W-2 income and investments, so it's worked well for my situation. I've heard similar concerns about more complex tax situations. Each tax prep software seems to have different strengths. FreeTax USA is better for more complex situations but requires more manual entry, while Cash App Taxes has better import features but might miss some of the more niche tax scenarios.
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Giovanni Ricci
Has anyone had issues with FreeTax USA calculating capital gains incorrectly? I manually entered my ETrade 1099-B info last year and my calculated tax seemed way off compared to what ETrade's tax summary showed.
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Yuki Yamamoto
•This usually happens because of wash sale adjustments or if you didn't properly classify long-term vs short-term gains. When you enter the data manually, it's easy to make small errors that compound. FreeTax USA's calculations are generally accurate, but garbage in = garbage out. Double check that your cost basis method matches what's on your ETrade forms, and that you've properly accounted for any wash sales that ETrade has flagged.
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The Boss
I've been using FreeTax USA for about 4 years now and while it doesn't have direct import from ETrade like TurboTax does, I've found a pretty efficient workflow for handling my investment income. For your 50+ transactions, definitely use the summary method that was mentioned earlier. ETrade actually provides a tax summary document along with your 1099-B that groups transactions by holding period and acquisition dates. You can use this to enter blocks of transactions rather than each individual trade. Also, make sure you're using ETrade's "Gain/Loss Realized" report which you can download as a CSV. While FreeTax USA can't import it directly, you can at least copy/paste chunks of data rather than typing everything from scratch. Just be extra careful about wash sales - ETrade marks them clearly but you need to make sure FreeTax USA applies the adjustments correctly. The time savings vs TurboTax fees has been totally worth it for me, even with the extra manual work.
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