[bojo]

Not the OP, however, I haven't found a product that's easy to drop options trading data into. I'd love to switch off of TurboTax, but I'm not putting hundreds of trades into a system manually - their import function makes it a breeze.

Perhaps it's time to hire an accountant?

[tedyoung]

Except for the 2nd year in a row, TurboTax fails to understand how to handle short put positions (of which I have many, many trades). It doesn't understand how the cost basis could be 0.

I'll have to short-circuit it _again_, and this will be the last year I use TurboTax: if I'm going to have to manually work around these things, I may as well not pay for the privilege. Prior years made it trivial to import the data from the 10 different financial firms that provide 1099s.

[xivzgrev]

do you have to document every trade?

At the end of the day the IRS cares about your net loss or gain, and what's short term vs long term gains.

So I typically sum up my various investments into those 2 buckets, by broker. if i ever get audited, i have the individual trades i can share if needed.

[bcrosby95]

It's right in the instructions for a 1040 that you must complete form 8949 if you have any capital gains or losses, and form 8949 says to list out each sale.

[junar]

This is not true for most folks, who can use one of two exceptions that allow summarizing. Exception 1 allows you to simply report totals on Schedule D. Exception 2 has you file Form 8949 with summarized rows, as long as you attach a statement with the detailed transaction info (the brokerage 1099-B generally suffices).

https://www.irs.gov/instructions/i8949#en_US_2021_publink594...

These are the very same exceptions that tax software uses.

[deathanatos]

Exception 1, I grant, and TIL. I sort of presume I can take that (in my situation), although this directive is confusing:

> The Ordinary box in box 2 isn’t checked

There is no "box 2" on the 1099-Bs I have. It is on the standardized IRS one, so the instruction from the IRS seems fine … but this is a great commentary on the state of the American tax system and how complicated it is.

(Variations on this theme cropped up multiple times during this year's prep, too…)

Exception 2 doesn't seem to list out what the conditions to qualify for it are, it only lists the procedure for the exception. I'm not sure how anyone is supposed to take it, for that reason.

> These are the very same exceptions that tax software uses.

TurboTax does not appear to take advantage of Exception 1. It would appear to have applied to my situation this year, and yet, TurboTax filled out a complete Form 8949, with each transaction, just like the parent comments hint at.

[junar]

If a particular box is not there, you can generally assume it was blank. Brokerages tend to produced a condensed 1099-B to save space: it would be very cumbersome parsing hundreds of pages of a full-IRS-layout 1099-B.

In practice, the condition for Exception 2 is "the 1099-B is already correct and you don't need to make further adjustments". Because if it isn't, you might as well fill out Form 8949.

It's definitely possible to have tax software summarize, although I suppose they might not do it by default.

https://ttlc.intuit.com/community/entering-importing/help/ho...

[deathanatos]

> If a particular box is not there, you can generally assume it was blank.

The tax code is just sufficiently complex enough that I don't feel safe making that assumption. You're probably right, but "probably" is too low a bar here.

> Brokerages tend to produced a condensed 1099-B to save space: it would be very cumbersome parsing hundreds of pages of a full-IRS-layout 1099-B.

… but like, isn't that the problem? If nobody uses the standardized form because it's too cumbersome … simplify the tax code.

Or standardize the data format and stop using PDF & human toil as a data transfer layer/format.

> It's definitely possible to have tax software summarize

Certainly it is possible. I was responding to the comment that it happens in practice, at least for the largest such software.

[formerkrogemp]

Yeah, I usually recommend freetaxusa but it sucks for putting in trade data.

[jandrese]

What do day traders and quants do? If you regularly trade hundreds of thousands of times per day do you end up submitting a semi-trailer worth of paper to the IRS every year?

[res0nat0r]

I'd recommend freetaxusa for everyone, I've been using that for years now. E-filing federal taxes is free, and state income tax E-filing are only something like $15 total. The interface is generally the same as TurboTax and is nice and easy.