Quick AnswerIf you pay quarterly estimated taxes late, the IRS may charge an underpayment penalty based on the amount you should have paid, when it was due, and how long it stayed unpaid. Paying late is still usually better than waiting until you file, but it may not...
Key TakeawaysFiling for bankruptcy does not automatically get rid of student loans. You usually have to take an extra legal step and prove repayment would create an undue hardship. If student loan debt is discharged, forgiven, settled, or canceled, the tax result...
Key TakeawaysThe IRS considers all sports betting payouts as ordinary income, regardless of the amount or whether you received a tax form. For the 2026 tax year, you can only deduct 90% of your gambling losses against your winnings, even if you ended the year...
Key TakeawaysA large refund is an interest-free loan to the government, while a big bill suggests you are at risk for IRS underpayment penalties. Updating your Form W-4 by late April allows you to spread adjustments across the majority of the year, minimizing the...
Key TakeawaysAs a W-2 employee, you pay half of Social Security and Medicare tax through withholding. As a self-employed taxpayer, you pay both halves through self-employment tax. Self-employment tax is 15.3% of your adjusted net earnings, and you also pay...
Key TakeawaysBusiness tax debt starts when tax money gets used to solve a cash flow problem somewhere else in the business. Payroll tax debt is especially dangerous because the IRS can sometimes hold owners and other responsible parties personally liable for...
