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Is anyone aware of any services (websites or programs) that allow completely free electronic filing for US form 1040 Tax returns for 2011, that include imports of many 1099-B / Capital Gains & Loss items like stock trades? (Not one-by-one manual entry)

Eg. TaxACTOnline.com doesn't fit the bill because the moment you try to import CSV files/spreadsheets of 1099-B transactions, or import in via Gainskeeper or otherwise from one of your brokerages, you have to pay for a deluxe version upgrade.

Not electing to attach a Form 8949 with the gains & cost basis info that still needs to get mailed separately to the IRS after the 1040 e-filing. I'm trying to avoid snail mail altogether.

I'm used to building my own Schedule D's (Capital Gains and Losses) based on these spreadsheets, or generate with the help of software, but want to file electronically freely as well. The IRS itself doesn't charge for that, rather prefer it to paper mail.

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    (Disclaimer I am a paid blogger at TurboTax' site) - Given the number of transactions you have, this is not the place to save money. Choose the brand, then stick with it, but paying $50 for whichever brand to be able to do what you need is pretty reasonable. A pro would probably be charging you $500+. – JoeTaxpayer Apr 17 '12 at 17:07
  • @JoeTaxpayer Kindly remove such opinions from here. The harm is that not only was it rather subjective and distracts from a very legitimate, timely question, but appears to be a missionary-style service class promotion. – Marcos Apr 17 '12 at 17:28
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    @Marcos - I don't know what was last year, but you CANNOT file with CalFile this year. Capital gains are explicitly excluded. Again, don't confuse "electronic filing" and "free filing". You can file electronically everything, but not for free. – littleadv Apr 17 '12 at 18:51
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    @marcos - there are risks involved with having such a complex return ("hundreds of trades") done via a free online service. Actually, my disclosure was an attempt to avoid the very accusation you launched. If I find such a free offering, I'll provide an answer, but for now my comment remains. – JoeTaxpayer Apr 17 '12 at 21:20
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    @marcos - My comment came from that particular fact. I'm all about squeezing the last cent out of a rock when I can. On the other hand, my time is money, as yours is, too. If you trade that much, time saved is time researching to find the next great trade. If you find the product you seek here, you should let others knows it's available. – JoeTaxpayer Apr 17 '12 at 21:35
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Tax professionals have informed me about indeed being able to file all summary information electronically oneself, and mailing Form 8949 later (eg. within 3 days after by IRS guidelines). Not all keep this timeline for their clients....

This is useful for otherwise simple Schedule D cases like mine in which rarely if ever might I intervene in the actual portfolio management transactions whose tax responsibility I ultimately take. Typically few trades (all performed by machine or outsourced, not by hand) of large lots, say 100 shares apiece, may get broken into volume-weighed equivalents such as even 1 or 2-share trades due to impact on markets, or whatever reasons, whose end result may be longer lists of transactions for current regulatory purposes. Granted, some situations may not apply to most individuals or may be too innovative/still not mainstream. Certainly that is TMI to include with the original question, but not realising different people may have different situations than one's own threw some people off topic.

In short, because something doesn't seem easy to find, it may not be ready yet. At the moment that seems like a possible best answer.

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