You can. It would just cost you so much in legal to not be worth it.

The reason it's worth it for these companies is because the number of zeroes involved. The legal costs are a rounding error for them.

Also true for just not paying taxes at all. The number of times I have had people tell me that they just let it float for years so they can settle up for a fraction later is unbelievable.

I know people who didn't pay taxes at all for years and the IRS came after them them several times (put them on payment plans that they didn't pay) before giving up. They now call us chumps for paying taxes. It is pretty absurd.

That sounds off. There's specific situations where the IRS will settle for less than the amount owed and they're not pleasant.

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Not true. It’s really common for 1099 people

What? You have to demonstrate financial hardship or risk getting convicted.

The people that get convicted seems to be either rich people blatantly evading taxes or people that write entire books about not paying taxes. Last I looked at the data for a normal person to get convicted just for running late on payments you basically have to tell the IRS to go fuck themselves and then brag about it publicly and stir up enough people they have to make an example out of you so no one else gets ideas. I'm sure there's odd other examples but they seem to be rare.

By and large the IRS wants to squeeze you for what they can get, not burn up a bunch of public resources convicting people and hindering their ability to earn more money for the IRS.