Do you have to report everything you earn to Social Security when receiving disability or retirement benefits?

$500 a month wouldn't affect ss benefits, but is enough that the person would have to report it to the IRS - self employment tax is due if they make over $400 for the YEAR from these. In both cases, there are plenty of ways they can get caught. Somebody reports them.... or maybe an IRS agents needs to get his computer fixed, or wants a t-shirt, and gets curious....... that's just a couple of many ways. Do people commit tax evasion? Sure they do. Do people get caught? Yup.