Many Americans face large unexpected tax bills in the spring due to insufficient planning. A late summer or early fall tax checkup can help avoid IRS penalties. Key questions to ask include: Did you take on a seasonal job? Earn freelance or gig income? Receive other untaxed income, such as interest or dividends? Sell valuable assets like stocks or cryptocurrency? Experience a filing status change (e.g., marriage)? If any of these apply, your tax withholding may not be enough. Use the IRS Withholding Estimator to check if adjustments are needed. IRS Withholding Estimator: Check Your Withholding.
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