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This might help annotating accumuated_sum:
from django.db.models import Subquery, IntegerField
class SQSum(Subquery):
output_field = IntegerField()
template = "(SELECT sum(outcome) from (%(subquery)s) _sum)"
accumulated_subquery = SQSum(
Roll.objects.filter(
pk__lte=OuterRef('pk')
).values("outcome")
)
Roll.objects.annotate(accumulated_sum=accumulated_subquery).filter(accumulated_sum__gte=amount)
Source:stackexchange.com