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 Tuning Your Social Security Benefit When should you take your Social Security benefit? Deciding When to Take Social Security One of the most common questions people ask about Social Security is when they should start taking benefits. Choose Your Own Retirement Adventure Retirement is one of the greatest adventures you’ll have. Which retirement adventure will you choose?