Money Here’s why your Social Security taxes might go up in 2019: A Foolish Take October 23, 2018 Dan Caplinger, The Motley Fool Comments Off on Here’s why your Social Security taxes might go up in 2019: A Foolish Take Some taxpayers will see as much as a $279 jump in the amount of tax they have to pay on Social Security. Find out if you're one of them.