diff --git a/tests/code_coverage_tests/check_licenses.py b/tests/code_coverage_tests/check_licenses.py
index 668aefa802..5fb2b495c2 100644
--- a/tests/code_coverage_tests/check_licenses.py
+++ b/tests/code_coverage_tests/check_licenses.py
@@ -31,6 +31,13 @@ DEFAULT_TRANSITIVE_PIN_PACKAGES = (
     "wheel",
 )
 
+# SPDX license expressions (PEP 639 "License-Expression") join identifiers with
+# the uppercase operators OR / AND / WITH. The split is case-sensitive: the
+# lowercase "-or-later" inside an identifier such as "GPL-2.0-or-later" is part
+# of the identifier, not an operator.
+_SPDX_OPERATOR_SPLIT = re.compile(r"\s+(?:OR|AND)\s+")
+_SPDX_WITH_SUFFIX = re.compile(r"\s+WITH\s+.*", re.DOTALL)
+
 
 @dataclass
 class PackageLicense:
@@ -109,21 +116,86 @@ class LicenseChecker:
     def get_package_license_from_pypi(
         self, package_name: str, version: str
     ) -> Optional[str]:
-        """Fetch license information for a package from PyPI."""
+        """Fetch license information for a package from PyPI.
+
+        Prefers the PEP 639 SPDX expression (``info.license_expression``),
+        falls back to the legacy free-text ``info.license`` field, and as a
+        last resort derives the license from the ``License :: OSI Approved ::
+        ...`` trove classifiers.
+        """
         try:
             url = f"https://pypi.org/pypi/{package_name}/{version}/json"
             response = requests.get(url, timeout=10)
             response.raise_for_status()
-            data = response.json()
-            return data.get("info", {}).get("license")
+            info = response.json().get("info", {}) or {}
+            return (
+                info.get("license_expression")
+                or info.get("license")
+                or self._license_from_classifiers(info.get("classifiers") or [])
+            )
         except Exception as e:
             print(
                 f"Warning: Failed to fetch license for {package_name} {version}: {str(e)}"
             )
             return None
 
-    def is_license_acceptable(self, license_str: str) -> Tuple[bool, str]:
-        """Check if a license is acceptable based on configured lists."""
+    @staticmethod
+    def _license_from_classifiers(classifiers: List[str]) -> Optional[str]:
+        """Derive a license name from the ``License :: OSI Approved :: ...`` trove classifiers."""
+        prefix = "License :: OSI Approved :: "
+        for classifier in classifiers:
+            if classifier.startswith(prefix):
+                license_name = classifier[len(prefix) :].strip()
+                if license_name:
+                    return license_name
+        return None
+
+    @staticmethod
+    def _split_spdx_expression(license_str: str) -> Optional[List[str]]:
+        """Split an SPDX license expression into its component identifiers.
+
+        Returns ``None`` when the string is not a recognizable SPDX expression
+        (for example a free-text license blob), so callers fall back to
+        whole-string matching.
+        """
+        if "OR" not in license_str and "AND" not in license_str:
+            return None
+
+        components: List[str] = []
+        normalized = license_str.replace("(", " ").replace(")", " ")
+        for part in _SPDX_OPERATOR_SPLIT.split(normalized):
+            # Drop any "WITH <exception>" suffix: the exception qualifies the
+            # preceding license, it is not itself a license to authorize.
+            identifier = _SPDX_WITH_SUFFIX.sub("", part).strip()
+            if not identifier:
+                continue
+            # SPDX short-form identifiers are single whitespace-free tokens; a
+            # component with internal whitespace means this is free text.
+            if any(char.isspace() for char in identifier):
+                return None
+            components.append(identifier)
+
+        return components if len(components) > 1 else None
+
+    def is_license_acceptable(self, license_str: Optional[str]) -> Tuple[bool, str]:
+        """Check if a license (or compound SPDX expression) is acceptable."""
+        if not license_str:
+            return False, "Unknown license"
+
+        components = self._split_spdx_expression(license_str)
+        if components is None:
+            return self._is_single_license_acceptable(license_str)
+
+        # Compound SPDX expression: conservatively require every component to
+        # be acceptable on its own (the safe direction for a CI gate).
+        for component in components:
+            is_acceptable, reason = self._is_single_license_acceptable(component)
+            if not is_acceptable:
+                return False, f"{reason} (in SPDX expression '{license_str}')"
+        return True, f"All SPDX components authorized: {', '.join(components)}"
+
+    def _is_single_license_acceptable(self, license_str: str) -> Tuple[bool, str]:
+        """Check if a single license identifier is acceptable based on configured lists."""
         if not license_str:
             return False, "Unknown license"
 
diff --git a/tests/code_coverage_tests/liccheck.ini b/tests/code_coverage_tests/liccheck.ini
index 0d1a6f0b04..5a09403c57 100644
--- a/tests/code_coverage_tests/liccheck.ini
+++ b/tests/code_coverage_tests/liccheck.ini
@@ -90,7 +90,6 @@ jinja2: >=3.1.4 # BSD 3-Clause License
 litellm-proxy-extras: >=0.1.1 # MIT License
 litellm-enterprise: >=0.1.1 # LiteLLM Enterprise License
 a2a-sdk: >=0.3.22 # Apache 2.0 license
-pydantic-settings: >=2.14.1 # MIT License manually verified (uses PEP 639 License-Expression: MIT, not the legacy License field, so liccheck reports it as unknown)
 anyio: >=4.5.0 # Unknown license
 httpx-aiohttp: >=0.1.4 # Unknown license
 backoff: >=2.2.1 # Unknown license
@@ -156,7 +155,6 @@ pytest: >=9.0.3 # MIT license
 pytest-postgresql: >=7.0.2 # LGPLv3+ license
 pytest-xdist: >=3.8.0 # MIT License
 ruff: >=0.15.3 # MIT License
-black: >=26.3.1 # MIT License manually verified (uses PEP 639 License-Expression: MIT, not the legacy License field, so liccheck reports it as unknown)
 types-requests: >=2.32.4.20260107 # Apache 2.0 license (typeshed)
 types-pyyaml: >=6.0.12.20250915 # Apache 2.0 license (typeshed)
 fakeredis: >=2.34.1 # BSD license
diff --git a/tests/test_litellm/test_check_licenses.py b/tests/test_litellm/test_check_licenses.py
new file mode 100644
index 0000000000..4d72f185a2
--- /dev/null
+++ b/tests/test_litellm/test_check_licenses.py
@@ -0,0 +1,211 @@
+"""Tests for the dependency license checker at tests/code_coverage_tests/check_licenses.py.
+
+Focus: PEP 639 license metadata. Packages that adopt PEP 639 publish their
+license as an SPDX expression in ``info.license_expression`` and often leave the
+legacy ``info.license`` field null, so the checker must read the new field (and
+fall back to trove classifiers) instead of reporting "Unknown license".
+
+PyPI HTTP responses are mocked — these tests never hit the network.
+"""
+
+import os
+import sys
+from pathlib import Path
+
+_CODE_COVERAGE_DIR = os.path.join(
+    os.path.dirname(os.path.abspath(__file__)), "..", "code_coverage_tests"
+)
+sys.path.insert(0, _CODE_COVERAGE_DIR)
+
+import check_licenses  # noqa: E402
+
+_LICCHECK_INI = Path(_CODE_COVERAGE_DIR) / "liccheck.ini"
+
+
+class _FakeResponse:
+    def __init__(self, payload):
+        self._payload = payload
+
+    def raise_for_status(self):
+        return None
+
+    def json(self):
+        return self._payload
+
+
+def _make_checker():
+    return check_licenses.LicenseChecker(config_file=_LICCHECK_INI)
+
+
+def _patch_pypi(monkeypatch, info):
+    """Make PyPI return a JSON response with the given ``info`` block."""
+
+    def _fake_get(url, timeout=None):
+        return _FakeResponse({"info": info})
+
+    monkeypatch.setattr(check_licenses.requests, "get", _fake_get)
+
+
+# --------------------------------------------------------------------------
+# get_package_license_from_pypi: license metadata resolution
+# --------------------------------------------------------------------------
+
+
+def test_get_license_prefers_license_expression(monkeypatch):
+    """(a) PEP 639 packages publish the SPDX expression in license_expression."""
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": "MIT", "license": None, "classifiers": []},
+    )
+    checker = _make_checker()
+    assert checker.get_package_license_from_pypi("black", "26.3.1") == "MIT"
+
+
+def test_license_expression_wins_when_both_present(monkeypatch):
+    """license_expression takes precedence over the legacy license field."""
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": "Apache-2.0", "license": "stale free text"},
+    )
+    checker = _make_checker()
+    assert checker.get_package_license_from_pypi("pkg", "1.0.0") == "Apache-2.0"
+
+
+def test_get_license_falls_back_to_legacy_license(monkeypatch):
+    """(b) Pre-PEP-639 packages only set the legacy free-text license field."""
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": None, "license": "MIT License", "classifiers": []},
+    )
+    checker = _make_checker()
+    assert checker.get_package_license_from_pypi("pkg", "1.0.0") == "MIT License"
+
+
+def test_get_license_falls_back_to_classifiers(monkeypatch):
+    """(c) Some packages express the license only through trove classifiers."""
+    _patch_pypi(
+        monkeypatch,
+        {
+            "license_expression": None,
+            "license": None,
+            "classifiers": [
+                "Programming Language :: Python :: 3",
+                "License :: OSI Approved :: Apache Software License",
+            ],
+        },
+    )
+    checker = _make_checker()
+    assert (
+        checker.get_package_license_from_pypi("pkg", "1.0.0")
+        == "Apache Software License"
+    )
+
+
+def test_get_license_returns_none_when_unset(monkeypatch):
+    """(d) With no license metadata at all the license stays unknown."""
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": None, "license": None, "classifiers": []},
+    )
+    checker = _make_checker()
+    assert checker.get_package_license_from_pypi("pkg", "1.0.0") is None
+
+
+def test_get_license_returns_none_on_request_failure(monkeypatch):
+    """Network/HTTP failures are swallowed and reported as unknown."""
+
+    def _boom(url, timeout=None):
+        raise RuntimeError("network down")
+
+    monkeypatch.setattr(check_licenses.requests, "get", _boom)
+    checker = _make_checker()
+    assert checker.get_package_license_from_pypi("pkg", "1.0.0") is None
+
+
+# --------------------------------------------------------------------------
+# is_license_acceptable: SPDX identifiers and compound expressions
+# --------------------------------------------------------------------------
+
+
+def test_spdx_identifiers_are_authorized():
+    """Plain SPDX identifiers match the legacy-spelled authorized list as-is."""
+    checker = _make_checker()
+    for identifier in ("MIT", "Apache-2.0", "BSD-3-Clause"):
+        is_ok, reason = checker.is_license_acceptable(identifier)
+        assert is_ok is True, f"{identifier}: {reason}"
+
+
+def test_spdx_compound_or_expression_is_authorized():
+    checker = _make_checker()
+    is_ok, reason = checker.is_license_acceptable("MIT OR Apache-2.0")
+    assert is_ok is True, reason
+
+
+def test_spdx_with_exception_in_compound_is_authorized():
+    """The 'WITH <exception>' suffix is stripped; the base license is checked."""
+    checker = _make_checker()
+    is_ok, reason = checker.is_license_acceptable(
+        "Apache-2.0 WITH LLVM-exception OR MIT"
+    )
+    assert is_ok is True, reason
+
+
+def test_spdx_gpl3_is_rejected():
+    """GPL-3.0 spellings must fail — they match no authorized license."""
+    checker = _make_checker()
+    for expr in ("GPL-3.0-only", "GPL-3.0-or-later"):
+        is_ok, reason = checker.is_license_acceptable(expr)
+        assert is_ok is False, f"{expr} unexpectedly accepted: {reason}"
+
+
+def test_spdx_compound_with_copyleft_component_is_rejected():
+    """A permissive-OR-copyleft expression is conservatively rejected."""
+    checker = _make_checker()
+    is_ok, _ = checker.is_license_acceptable("MIT OR GPL-3.0-only")
+    assert is_ok is False
+
+
+def test_or_later_identifier_is_not_split_as_operator():
+    """The lowercase '-or-later' inside an identifier is not the SPDX OR operator."""
+    assert (
+        check_licenses.LicenseChecker._split_spdx_expression("GPL-2.0-or-later") is None
+    )
+
+
+def test_free_text_license_is_not_treated_as_spdx():
+    """Free-text license blobs fall back to whole-string substring matching."""
+    free_text = "MIT License AND additional redistribution permissions"
+    assert check_licenses.LicenseChecker._split_spdx_expression(free_text) is None
+    checker = _make_checker()
+    assert checker.is_license_acceptable(free_text)[0] is True
+
+
+def test_unknown_license_is_reported():
+    checker = _make_checker()
+    is_ok, reason = checker.is_license_acceptable(None)
+    assert is_ok is False
+    assert reason == "Unknown license"
+
+
+# --------------------------------------------------------------------------
+# check_package: end-to-end resolution + acceptability
+# --------------------------------------------------------------------------
+
+
+def test_check_package_accepts_pep639_package(monkeypatch):
+    """A PEP 639 package whose license lives only in license_expression passes."""
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": "MIT", "license": None, "classifiers": []},
+    )
+    checker = _make_checker()
+    assert checker.check_package("some-pep639-pkg", "1.0.0") is True
+
+
+def test_check_package_rejects_package_without_license(monkeypatch):
+    _patch_pypi(
+        monkeypatch,
+        {"license_expression": None, "license": None, "classifiers": []},
+    )
+    checker = _make_checker()
+    assert checker.check_package("mystery-pkg", "1.0.0") is False