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Re:IRS Reforms Free File Program, Drops Agreement Not to Com... by adventured on Wednesday January 01, 2020 @02:46AM (#21927124)
Ever performed a lot of stock trades in a single year and had the IRS believe that you owe them $5 million in income taxes because they assume every sale you made was all profit? That's always fun, especially when they think they're right and they're entirely wrong.

The IRS information is at times comically incorrect in fact.

Re:IRS Reforms Free File Program, Drops Agreement Not to Com... by fountainofage on Wednesday January 01, 2020 @04:16AM (#21927341)
If you're trading more than $20 million a year in stocks, you are in the vast minority that everyone here acknowledges would need to adjust and file your taxes manually.

99.999% of the US population is not trading $20 million a year in stocks, and everyone else here is merely talking about the 95% of the population that has straightforward tax returns.

Re:IRS Reforms Free File Program, Drops Agreement Not to Com... by phonon on Wednesday January 01, 2020 @11:03AM (#21928563)
Cost basis reporting from brokers to the IRS has been around for several years.
Re:IRS Reforms Free File Program, Drops Agreement Not to Com... by azinman2 on Wednesday January 01, 2020 @06:07AM (#21927592)
Which is why most countries have a system that shows you what they think, and you can accept or not. It’s not like the majority of people are in such a situation, and likely over time that will become less common as its often a byproduct of legacy systems / mergers that lose the original transaction.