diff --git a/litellm/proxy/common_utils/fips.py b/litellm/proxy/common_utils/fips.py
index f57f56d3248..671c023bbdb 100644
--- a/litellm/proxy/common_utils/fips.py
+++ b/litellm/proxy/common_utils/fips.py
@@ -31,13 +31,20 @@ def openssl_enforces_fips() -> bool:
 
 
 def cryptography_enforces_fips() -> bool:
-    """The cryptography library's own OpenSSL runs with FIPS-only defaults."""
+    """The cryptography library's own OpenSSL runs with FIPS-only defaults and its FIPS provider can hash SHA-256."""
     try:
+        from cryptography.exceptions import InternalError, UnsupportedAlgorithm
         from cryptography.hazmat.bindings._rust import openssl as rust_openssl
-
-        return rust_openssl.is_fips_enabled()
-    except (ImportError, AttributeError):
+        from cryptography.hazmat.primitives import hashes
+    except ImportError:
         return False
+    try:
+        if not rust_openssl.is_fips_enabled():
+            return False
+        hashes.Hash(hashes.SHA256()).finalize()
+    except (AttributeError, InternalError, UnsupportedAlgorithm):
+        return False
+    return True
 
 
 def enforce_fips_mode() -> None:
@@ -63,6 +70,7 @@ def enforce_fips_mode() -> None:
         )
     if not cryptography_enforces_fips():
         raise FipsModeError(
-            f"{FIPS_MODE_ENV_VAR} is on but the cryptography library's OpenSSL does not enforce FIPS. Build it against "
-            f"the system OpenSSL (pip install --no-binary cryptography cryptography), or unset {FIPS_MODE_ENV_VAR}."
+            f"{FIPS_MODE_ENV_VAR} is on but the cryptography library's OpenSSL has no working FIPS provider. Build it "
+            "against the system OpenSSL (pip install --no-binary cryptography cryptography), or unset "
+            f"{FIPS_MODE_ENV_VAR}."
         )
diff --git a/tests/unit/proxy/common_utils/test_fips.py b/tests/unit/proxy/common_utils/test_fips.py
index 98e95263dcb..bd6834af536 100644
--- a/tests/unit/proxy/common_utils/test_fips.py
+++ b/tests/unit/proxy/common_utils/test_fips.py
@@ -1,8 +1,11 @@
 import _hashlib
 from contextlib import nullcontext
+from unittest.mock import Mock
 
 import pytest
+from cryptography.exceptions import InternalError
 from cryptography.hazmat.bindings._rust import openssl as rust_openssl
+from cryptography.hazmat.primitives import hashes
 
 import litellm
 from litellm.proxy.common_utils.fips import (
@@ -50,10 +53,18 @@ def test_openssl_without_get_fips_mode_does_not_enforce_fips(monkeypatch):
     assert openssl_enforces_fips() is False
 
 
-@pytest.mark.parametrize("fips_enabled", [True, False])
-def test_cryptography_enforces_fips_reads_its_openssl_fips_flag(monkeypatch, fips_enabled):
+@pytest.mark.parametrize(
+    "fips_enabled, sha256_broken, enforces",
+    [(True, False, True), (False, False, False), (True, True, False)],
+    ids=["fips", "fips-flag-off", "sha256-broken"],
+)
+def test_cryptography_enforces_fips_needs_the_fips_flag_and_a_working_sha256(
+    monkeypatch, fips_enabled, sha256_broken, enforces
+):
     monkeypatch.setattr(rust_openssl, "is_fips_enabled", lambda: fips_enabled)
-    assert cryptography_enforces_fips() is fips_enabled
+    if sha256_broken:
+        monkeypatch.setattr(hashes, "Hash", Mock(side_effect=InternalError("Unknown OpenSSL error", [])))
+    assert cryptography_enforces_fips() is enforces
 
 
 def test_cryptography_without_is_fips_enabled_does_not_enforce_fips(monkeypatch):
@@ -78,7 +89,7 @@ def test_this_runners_openssl_does_not_enforce_fips():
         ("true", "false", True, True, True, "TLS certificate verification is disabled"),
         ("true", None, False, True, True, "TLS certificate verification is disabled"),
         ("true", None, True, False, True, "is on but OpenSSL does not enforce FIPS"),
-        ("true", None, True, True, False, "cryptography library's OpenSSL does not enforce FIPS"),
+        ("true", None, True, True, False, "cryptography library's OpenSSL has no working FIPS provider"),
         ("enforced", None, True, True, True, "LITELLM_FIPS_MODE='enforced' is not a boolean"),
     ],
     ids=[