Why am I being penalized $165 for underpayment of estimated taxes. I made $18,175 in Miscellaneous Income. Should I have estimated taxes and paid earlier in the year?

[Ashby · Accepted solution]

Unfortunately, yes, that's what the IRS expects you to do. It's considered a "pay-as-you-go" tax system. It's the same reason why people with paychecks get taxes withheld as the money comes in. 

So, if you have income without withholdings, you are expected to send in quarterly tax payments. TurboTax should supply you with 1040-ES payment vouchers based on you "underpaying" last year.

The payment due dates are 4/15, 6/15, 9/15, and 1/15.