Julia, 3
A simple one just to get the ball rolling...
Initial program:
inquisition
Error 1:
inquisition not defined
It may not be defined, but if it's Spanish, it's also unexpected. Nobody expects the Spanish Inquisition.
Error 2:
syntax: extra token "not" after end of expression
Error 3:
syntax: extra token "token" after end of expression
The third error message, when submitted as a program, produces that same error, hence the score of 3.
Work in progress! Surely I can do better than 3.