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This question came to me from over thinking the "Angulimala" story. He had to "repent" to some extent for the murders he committed, by being scolded an hit by stones. However, the effect of the karma seems to be quite mild for 999 murders and even the intention to kill the Buddha.
So my question is this: Does your karma have to be neutral or positive to become enlightened? And if not, what happens to the negative karma after attaining enlightenment?
While some of the past karma may fruit as obstacles to liberation, not all karma has to fruit before liberation, as even Buddha himself famously experienced results of his past karma after his enlightenment (e.g. when Devadatta wounded the Buddha's foot with a rock).
As I explained in https://buddhism.stackexchange.com/a/1672/43 Buddha rejected the theory of intentionally "burning" past karma through exertion and austerity. Instead, liberation is achieved by "abandoning of unskillful mental qualities and the attainment of skillful mental qualities in the here-&-now".
Basically, Buddha's advice to people of difficult backgrounds has usually been to leave the past in the past, and focus on the choices to be made and the state of mind to be maintained from now on.
No, you don't need to deplete all your good or bad kamma to become enlightened, it does happen with "remaining" kamma.
Regarding Angulimala, there is a beautiful simile the Buddha gave that might help you understand:
Imagine you take some salt with your hands and put it in a glass of water, the water will be salty, terrible to drink
Now imagine you take the same amount of salt and throw it in the river, the water in the river will not taste bad. The salt is the bad kamma and the water the good kamma, so if you do a lot of good kamma, that will positively impact your future even if you have lots of bad kamma, Angulimala became a monk and did a lot of good kamma, neutralizing (at least partially) the impacts of his terrible bad kamma.
You have to deplete all your Karma giving rebirth in the 4 lower realms to gain the 1st stage of sainthood. To be a fully enlightened person you have to deplete all Karma leading to rebirth.
This does not mean you deplete all Karma. Some Karma are only effective after rebirth can remain as a residue but all Karma which would give a rebirth should be removed.
The process of Vippassana is the process of un working of Karma / removing fabrications where by which you remove the effects of Karma. The Karma surfaces as a sensation and passes away.
Also note there 5 grave offences which will always give result in the next life. As Angulimala has not committed such Karma the others will pass away through the practice of Vippassana.
In vipassana meditation, the practitioner have to stop the arising of unwholesome consciousness by jhana meditation. If unwholesome consciousness still arise between vipassana meditation, the practitioner can not enlighten.
Another the resultant of unwholesome consciousness will not arise anymore after arahanta die.
