For anyone trying to get this achievement on July 2016 and onward, please read:
First, play The Breaking on Legendary (solo is harder and below is how you'll get it).WARNING
DO NOT RELOAD FROM LAST CHECKPOINT. This nullifies the achievement. Here's what you must do.
1. Every once in a while, manually save your game in one of the three save slots.
2. Whenever you die, immediately press START (
) and LEAVE GAME. DO NOT LET THE GAME RELOAD FROM LAST CHECKPOINT OR SHOW A "GAME OVER".
3. Go back to Solo Campaign and click LOAD GAME and select the save file you manually saved. This will place you somewhere near where you saved the game.
4. Repeat every time you die.Edit:
Please turn off all skulls just to be sure nothing goes wrong. I know at least one achievement in Halo 5 can be bugged with skulls turned on so please turn them off for this one as well.