First, we need to convert the mixed number 2 3/8 to an improper fraction:
2 3/8 = (2 x 8 + 3) / 8 = 19/8
To find out how many times Craig needs to fill a 1/3 cup measuring cup, we can divide 19/8 by 1/3:
(19/8) / (1/3) = (19/8) x (3/1) = 57/8
Therefore, Craig needs to fill a 1/3 cup measuring cup 57/8 times to measure 2 3/8 cups.