Bug fixes
In the solution for runner.py runner.consecutive_wins is not defined and it should be reset if a wrong answer is given.
Furthermore, I get a NameError if I type 'y' to continue playing so I would suggest using raw_input() in both the excercise and the solution.
I also faced this error while trying this tutorial and as per @ckiefer0's suggestion using raw_input will obviously fix it for python 2.x versions but will break it for python 3 as raw_input() is completely replaced by input() and will end up raising NameError: name 'raw_input' is not defined.
The solution also does not reroll the dice. It may be better to remove solutions entirely if it doesn't work. It only confuses the readers.