Does

  constraint_factory.create_from_chain(
      ForEach(Shift)
      | Filter(lambda shift: shift.required_skill not in shift.employee.skills)
      | Penalize(HardSoftScore.ONE_HARD)
      | AsConstraint("Missing required skill")
  )

Feel more Pythonic than

  (
      constraint_factory.for_each(Shift)
      .filter(lambda shift: shift.required_skill not in shift.employee.skills)
      .penalize(HardSoftScore.ONE_HARD)
      .as_constraint("Missing required skill")
  )

?