<prompt> Human: Im paying like 2k in federal and 700 in state per month. As long as I keep my eye on the numbers and have the cash to pay the governments, I should be fine right?  <response>: From the IRSs website: If you didnt pay enough tax throughout the year, either through withholding or by making estimated tax payments, you may have to pay a penalty for underpayment of estimated tax. And: You may have to pay a penalty of 500 if both of the following apply. You make statements or claim withholding allowances on your Form W-4 that reduce the amount of tax withheld. You have no reasonable basis for those statements or allowances at the time you prepare your Form W-4. There is also a criminal penalty for willfully supplying false or fraudulent information on your Form W-4 or for willfully failing to supply information that would increase the amount withheld. The penalty upon conviction can be either a fine of up to 1,000 or imprisonment for up to 1 year, or both. These penalties will apply if you deliberately and knowingly falsify your Form W-4 in an attempt to reduce or eliminate the proper withholding of taxes. 