News for hackers. Stuff that matters.
Re:IRS will look into setting up a free e-filing system by jjav on Wednesday September 07, 2022 @03:04PM (#32754972)
> Which bunch of shares did you sell? Was it a short term gain or a long term gain? Was it a loss? It depends. Neither your broker or IRS knows the answer, but you do.

Your broker does know because you need to tell them which ones to sell when you sold.

The IRS also knows because that's included in the cost basis reported to them by the broker. (This changed some number of years ago, brokers used to only report the income from the sale but not the cost.)

https://www.spencerlawfirm.com/2011/01/new-cost-basis-report...

Re:IRS will look into setting up a free e-filing system by jjav on Saturday September 10, 2022 @04:48AM (#32788981)
I should add to this, even though the broker reports the cost basis, be proactive in verifying that it is correct.

For reasons I can't comprehend, ETrade reports the costs basis wrong every single year on all my RSU and ESPP sold shares. They do issue a supplemental report which has all the correct info, but the 1099-B has it wrong. It is maddening. I need to send both the 1099 and the supplemental doc to my CPA so things are accounted correctly, otherwise I'd pay a lot more taxes due to ETrade errors.

All other brokers I deal with do it correctly.

Re:IRS will look into setting up a free e-filing system by ryandrake on Wednesday September 07, 2022 @03:06PM (#32755007)
Interesting. I learned something today. Thanks.
Re:IRS will look into setting up a free e-filing system by seanp2k2 on Wednesday September 07, 2022 @03:33PM (#32755514)
...and therefore there is even less reason for the IRS to not pre-fill forms or just have an exception-based filing system vs everyone has to file regardless of exceptions / amendments / challenges etc.
Re:IRS will look into setting up a free e-filing system by spoils19 on Wednesday September 07, 2022 @06:46PM (#32758171)
What about including the free market of tax helper systems and services? You'll be wiping out an entire industry - doesn't seem very conservative to me.
Re:IRS will look into setting up a free e-filing system by oblio on Wednesday September 07, 2022 @09:10PM (#32759729)
We should bring back the entire industry of leech breeders and sellers for bloodletting, too.