<prompt> Human: I am trying to determine if it makes financial sense for me to make quarterly tax payments to the IRS.I have a full-time job making 100k. Last year I made a decent amount on the side from stocks, about 75k. I qualify for safe harbor this year since my withholding was 100 of my prior years tax liability. So I owe a fairly significant amount for my 2016 taxes about 18k.I anticipate making at least as much, if not more, this year through trading. I am trying to determine what my penalty will be if I dont make estimated quarterly payments this year vs. what I could do with that money through investing.If I make quarterly payments, they would be about 5k-5.5k per quarter. Thats about 21k for the year. If the penalty is only 3 about 700 I know that I can use that money to make a ton more to cover the penalty and then some.So am I missing something here? Why wouldnt everyone just pay the penalty who is in this type of situation?EDIT:The comments seem to be focusing on my confidence to make more than 3. Lets just go on the assumption that Im guaranteed to make say 20 or more. Does it make sense to make quarterly payments in that scenario? Is there some pitfall that Im not aware of?Assistant: Many do, and thats the reason why tax attorneys have jobs. The way this typically plays out is that investors operate in a market where you cant swing a dead cat without slamming into three or four stocks that will make a profitable return over the course of a year. Because people have short memories and a terrible sense of history, they expect that this will continue. Something happens, the market crashes on 02JAN18 or some similarly timed event and the taxpayer is out of liquidity. You then need to sell off a huge position or go into debt to pay the tax bill. This was very common in 2008 and 1999. Quarterly estimates are intelligent to pay if for no other reason than because youre limiting risk in an already outrageously risky enterprise.Human: Im not an investor. Im a trader. My strategy is pretty immune to crashes.Assistant: Yeah, okay. Im sure you found the one trick that banks hate. Unless youre making markets and youre not, since youre not making enough and dont have the assets to accomplish that, youve got exposure to macroeconomic trends.Human: Not to beat a dead horse, but I know what Im doing. Ive spent years perfecting what I do. My strategy actually performs better during crashes.This is going off on a tangent. Lets just assume that I know Ill make way more than 3 this year and will have the liquidity to pay my tax bill every April.  <response>: If youre making that much money and are impervious to everything and know something that multibillion dollar corporations dont, you should still pay the quarterly estimates because the marginal gain associated with not paying them is minimal and tax compliance issues will ruin your life. There is a reason why GS doesnt screw around with taxes and it isnt because they are hunting for 1 arbitrage gains. 