Graph pebbling models the transportation of consumable resources. As two pebbles move across an edge, one reaches its destination while the other is consumed. The $t$-pebbling number is the smallest integer $m$ so that any initially distributed supply of $m$ pebbles can place $t$ pebbles on any target vertex via pebbling moves. The 1-pebbling number of diameter two graphs is well-studied. Here we investigate the $t$-pebbling number of diameter two graphs under the lense of connectivity.