Failure to make estimated tax payments
One of the most frequent compliance pitfalls for individuals is the failure to make estimated tax payments. This issue often affects self-employed individuals, independent contractors, and those with significant income from sources not subject to withholding. The U.S. tax system operates on a “pay-as-you-go” basis, requiring taxpayers to pay taxes throughout the year rather than solely at filing time. Many individuals mistakenly believe they can settle their entire tax bill when filing their annual return, leading to penalties and interest.