Social Security Taxes Estimate how much of your Social Security benefit may be considered taxable. You are viewing this website at a small screen resolution which doesn't support calculators. Click here to view this calculator. Have A Question About This Topic? Name Email Address Message Thank you! Oops! Related Content When Life Insurance Becomes Taxable Life insurance proceeds are generally tax-free. But not in all cases. Investment Challenges of the Affluent Investor Affluent investors face unique challenges when putting together an investment strategy. Make sure you keep these in mind. Protecting Your Business from the Loss of a Key Person Business owners may be able to protect themselves from the financial consequences of losing a key employee.