<prompt> Human: I work two regular jobs W2s and do extra work as a freelance musician. For tax purposes, I claim 1 exemption at one job, and 0 exemptions at the other as a single guy with no kids, so I should be paying more than I owe overall. Most of my freelance work is paid to me without deductions, and I receive a MISC-1099 at the end of the year.My question is, do I need to make estimated tax payments on the untaxed income? Or will it be alright as long as it all balances out with the taxes Ive paid through my other two jobs? Ive been hit with underpayment penalties before, and hope to avoid that this year.  <response>: Yes, if you over with-hold on your W-2 jobs, then you dont need to make estimated payments for your free lance job. You need to have paid 90 of your current year tax liability come tax time to avoid underpayment penalties its slightly more complicated but thats a general rule and since youll be making regular payments with your W-2 withholding then you should be fine. If you expect your freelance income to increase this year but your W-2 income to stay the same and your deductions to stay the same or decrease - as compared to last year - youll want to make estimated payments, because you will be underpaid. I would suggest that when you get your last paychecks of the year you take your check stubs and do a quick estimate of your taxes with your freelance income and see if you come out OK. If not, make a Q4 estimated payment by 1152016.My SOs dad severely over-withholds on his pension so that he doesnt have to bother with making estimated payments he works 1099 jobs as a security guard and this works for him. 