from __future__ import annotations

from packaging.version import Version
from typing import Optional


def parse_version(version_str: str) -> Optional[Version]:
    try:
        return Version(version_str)
    except Exception:
        return None


def compare_versions(v1: str, v2: str) -> int:
    parsed_v1 = parse_version(v1)
    parsed_v2 = parse_version(v2)
    if parsed_v1 is None or parsed_v2 is None:
        return 0
    if parsed_v1 < parsed_v2:
        return -1
    elif parsed_v1 > parsed_v2:
        return 1
    return 0


def is_version_outdated(current: str, latest: str) -> bool:
    return compare_versions(current, latest) < 0


def extract_version_from_specifier(specifier: str) -> Optional[str]:
    if not specifier:
        return None
    operators = ["===", "==", ">=", "<=", "~=", "!=", ">", "<", "^", "~"]
    for op in operators:
        if specifier.startswith(op):
            return specifier[len(op):].strip()
    return specifier.strip()