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I think this might be due to business income, as w2 is usually ok for me each year. This is the first year the business made income and this is the first time i see this underpayment screen. I did not pay any taxes ahead during the year on this business income. That might be the issue? If so how does this work when there are more expenses than income, so in this case should I still be paying quarterly taxes on business income? During the year I knew there will be more expenses than income based on trend so the earning would be offset by losses. Wouldn't that mean there should be no net income and no taxes due?