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Assume it is given that you need to itemize trades on, say, Form 8949 (+ any state form(s)). These forms only allow so many transactions per page (14 entries for Form 8949).

How exactly do people who have thousands of transactions to itemize (or tens or hundreds of thousands...) deal with this? Does the IRS really want to receive hundreds or thousands of pages of transactions?

And I suppose people e-file if they are willing and able to, but what about those who prefer to and/or are required to file by mail? Do they send entire reams of paper to the IRS? Or do federal & state governments provide a more practical solution?

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  • Why would anyone who can file electronically prefer to print and mail paper?? It will take many months instead of days to process. – Aganju Apr 1 at 18:47
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    @Aganju: Filing electronically requires disclosing all your personal info to third parties whose privacy practices you may not like. – user541686 Apr 1 at 20:39
  • point taken. Thanks. – Aganju Apr 1 at 22:56
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I think that 2008 was the last year before electronic filing took place. My 8949 form was 832 pages (over a ream and a half of paper!) and it took me all day to print it.

Now, brokerage firms report 1099 and 8949 forms to the IRS and I just report the 8949 totals. I've never had a complaint from the IRS since 2008.

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  • Wow I see, thanks. Could you clarify what you mean by just reporting 8949 totals for brokerages that report to the US? I know TurboTax fills out multiple 8949s, seemingly to account for every stock trade, on top of the 1099-B that it includes in your return. Is this some kind of simplification you can do only if you FIFO everything? – user541686 Apr 1 at 23:05
  • I really don't know much about this other than my broker provides a 1099 and an 8949. When I used to trade heavily, I subscribed to Tradelog, a tax accounting program for traders, mainly because I have found errors in my broker's reports. The disclaimer at the bottom of my broker's reports is heartwarming :->) – Bob Baerker Apr 2 at 0:22
  • Oh wow I see, okay that's still great information, thanks! – user541686 Apr 2 at 0:44
  • If a tax accounting program interests you, also look into Gainskeeper. – Bob Baerker Apr 2 at 1:21
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    In that case, my 2008 8949 information (or equivalent) came from Tradelog. What I learned in 2008 was that if you trade heavily with wash sales and you scale in and out of positions, it's a freaking nightmare to reconcile. Hence the reason that I subscribed to Tradelog. – Bob Baerker Apr 2 at 2:37
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One way to get them there is to import them electronically - many brokers and most tax software support this.
I got 2300 transactions from one broker imported (and submitted to the IRS) without a problem; but I can‘t tell you how TurboTax spread it technically on many pages, I never looked.

Alternatively, you can total them for each category, and enter one total line only, each for short term covered, long term covered, etc.

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  • Interesting, thanks. You can't aggregate long-term though, can you? The only aggregation provision I see here is for short-term: "You may aggregate all short-term transactions reported on Form(s) 1099-B showing basis was reported to the IRS and for which no adjustments or codes are required. Enter the totals directly on Schedule D, line 1a; you aren’t required to report these transactions on Form 8949 (see instructions)." If you have more info you might be able to link to that'd be awesome. – user541686 Apr 1 at 23:08
  • @user541686: I don't know what you're reading, but the Schedule D instructions for lines 1a and 18a clearly specify both short and long. – dave_thompson_085 Apr 2 at 2:01
  • Oh interesting, I was reading form 8949, but I didn't realize the second page says the same thing for long-term. Thanks for pointing it out! – user541686 Apr 2 at 2:05

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