diff --git a/sdk/identity/azure-identity/CHANGELOG.md b/sdk/identity/azure-identity/CHANGELOG.md
index 061a653e837e..157821d16612 100644
--- a/sdk/identity/azure-identity/CHANGELOG.md
+++ b/sdk/identity/azure-identity/CHANGELOG.md
@@ -13,6 +13,7 @@
 ### Bugs Fixed
 
 - Fixed the `AZURE_REGIONAL_AUTHORITY_NAME` environment variable not being respected in certain credentials. ([#44347](https://github.com/Azure/azure-sdk-for-python/pull/44347))
+- Fixed an issue with certain credentials not bypassing the token cache when claims are provided in `get_token` or `get_token_info` calls. ([#44552](https://github.com/Azure/azure-sdk-for-python/pull/44552))
 
 ### Other Changes
 
diff --git a/sdk/identity/azure-identity/azure/identity/_credentials/shared_cache.py b/sdk/identity/azure-identity/azure/identity/_credentials/shared_cache.py
index 0ef0e5b6d3da..4ee7aa187ee7 100644
--- a/sdk/identity/azure-identity/azure/identity/_credentials/shared_cache.py
+++ b/sdk/identity/azure-identity/azure/identity/_credentials/shared_cache.py
@@ -185,9 +185,10 @@ def _get_token_base(
 
         account = self._get_account(self._username, self._tenant_id, is_cae=is_cae)
 
-        token = self._get_cached_access_token(scopes, account, is_cae=is_cae)
-        if token:
-            return token
+        if not claims:
+            token = self._get_cached_access_token(scopes, account, is_cae=is_cae)
+            if token:
+                return token
 
         # try each refresh token, returning the first access token acquired
         for refresh_token in self._get_refresh_tokens(account, is_cae=is_cae):
diff --git a/sdk/identity/azure-identity/azure/identity/_internal/aad_client_base.py b/sdk/identity/azure-identity/azure/identity/_internal/aad_client_base.py
index 876ba56a5c7e..b40574d8f2e6 100644
--- a/sdk/identity/azure-identity/azure/identity/_internal/aad_client_base.py
+++ b/sdk/identity/azure-identity/azure/identity/_internal/aad_client_base.py
@@ -92,6 +92,9 @@ def _initialize_cache(self, is_cae: bool = False) -> TokenCache:
         return cast(TokenCache, self._cae_cache if is_cae else self._cache)
 
     def get_cached_access_token(self, scopes: Iterable[str], **kwargs: Any) -> Optional[AccessTokenInfo]:
+        # Do not return a cached token if claims are provided.
+        if kwargs.get("claims"):
+            return None
         tenant = resolve_tenant(
             self._tenant_id, additionally_allowed_tenants=self._additionally_allowed_tenants, **kwargs
         )
diff --git a/sdk/identity/azure-identity/azure/identity/aio/_credentials/shared_cache.py b/sdk/identity/azure-identity/azure/identity/aio/_credentials/shared_cache.py
index 0d14c508ec9b..2c27af171517 100644
--- a/sdk/identity/azure-identity/azure/identity/aio/_credentials/shared_cache.py
+++ b/sdk/identity/azure-identity/azure/identity/aio/_credentials/shared_cache.py
@@ -138,9 +138,10 @@ async def _get_token_base(
 
         account = self._get_account(self._username, self._tenant_id, is_cae=is_cae)
 
-        token = self._get_cached_access_token(scopes, account, is_cae=is_cae)
-        if token:
-            return token
+        if not claims:
+            token = self._get_cached_access_token(scopes, account, is_cae=is_cae)
+            if token:
+                return token
 
         # try each refresh token, returning the first access token acquired
         for refresh_token in self._get_refresh_tokens(account, is_cae=is_cae):
diff --git a/sdk/identity/azure-identity/tests/test_aad_client.py b/sdk/identity/azure-identity/tests/test_aad_client.py
index 6facdafb4629..56148e39ce72 100644
--- a/sdk/identity/azure-identity/tests/test_aad_client.py
+++ b/sdk/identity/azure-identity/tests/test_aad_client.py
@@ -451,3 +451,36 @@ def test_claims(method, args):
         assert post_mock.call_count == 2
         data, _ = post_mock.call_args
         assert data[0]["claims"] == cae_merged_claims
+
+
+def test_get_cached_access_token_with_claims():
+    """When claims are provided, get_cached_access_token should return None even if a token is cached"""
+
+    client_id = "client-id"
+    scope = "scope"
+    cached_token = "cached-access-token"
+    tenant_id = "tenant"
+    authority = "https://localhost/" + tenant_id
+    claims = '{"access_token": {"nbf": {"essential": true, "value": "1234567890"}}}'
+
+    # Add a valid token to the cache
+    cache = TokenCache()
+    cache.add(
+        {
+            "response": build_aad_response(access_token=cached_token, expires_in=3600),
+            "client_id": client_id,
+            "scope": [scope],
+            "token_endpoint": "/".join((authority, tenant_id, "oauth2/v2.0/token")),
+        }
+    )
+
+    client = AadClient(tenant_id=tenant_id, client_id=client_id, authority=authority, cache=cache)
+
+    # Without claims, the cached token should be returned
+    token = client.get_cached_access_token([scope])
+    assert token is not None
+    assert token.token == cached_token
+
+    # With claims, should return None even though a valid token is cached
+    token_with_claims = client.get_cached_access_token([scope], claims=claims)
+    assert token_with_claims is None
diff --git a/sdk/identity/azure-identity/tests/test_shared_cache_credential.py b/sdk/identity/azure-identity/tests/test_shared_cache_credential.py
index 5ab9c08db482..f1c64da124a9 100644
--- a/sdk/identity/azure-identity/tests/test_shared_cache_credential.py
+++ b/sdk/identity/azure-identity/tests/test_shared_cache_credential.py
@@ -974,6 +974,71 @@ def test_claims_challenge(get_token_method):
     assert kwargs["claims_challenge"] == expected_claims
 
 
+@pytest.mark.parametrize("get_token_method", GET_TOKEN_METHODS)
+def test_claims_skips_cached_access_token(get_token_method):
+    """When claims are provided, the credential should skip cached access tokens and request a new one"""
+
+    scope = "scope"
+    expected_claims = '{"access_token": {"nbf": {"essential": true, "value": "1234567890"}}}'
+    cached_access_token = "cached-access-token"
+    first_refresh_token = "first-refresh-token"
+    second_refresh_token = "second-refresh-token"
+
+    username = "user@example.com"
+    uid = "uid"
+    utid = "utid"
+
+    # Set up cache with an access token and refresh token
+    account = get_account_event(username=username, uid=uid, utid=utid, refresh_token=first_refresh_token)
+    cache = TokenCache()
+    cache.add(account)
+
+    # First request without claims - this will cache an access token
+    transport = validating_transport(
+        requests=[Request(required_data={"refresh_token": first_refresh_token})],
+        responses=[
+            mock_response(
+                json_payload=build_aad_response(
+                    uid=uid,
+                    utid=utid,
+                    access_token=cached_access_token,
+                    refresh_token=second_refresh_token,
+                    id_token=build_id_token(
+                        aud=DEVELOPER_SIGN_ON_CLIENT_ID, object_id=uid, tenant_id=utid, username=username
+                    ),
+                )
+            )
+        ],
+    )
+    credential = SharedTokenCacheCredential(_cache=cache, transport=transport)
+    token = getattr(credential, get_token_method)(scope)
+    assert token.token == cached_access_token
+
+    # Verify the access token is now cached - second request without claims should use it
+    credential = SharedTokenCacheCredential(
+        _cache=cache, transport=Mock(send=Mock(side_effect=Exception("should use cached token")))
+    )
+    token = getattr(credential, get_token_method)(scope)
+    assert token.token == cached_access_token
+
+    # Now request with claims - should bypass the cached access token and use refresh token
+    new_token_with_claims = "new-access-token-with-claims"
+    transport = validating_transport(
+        requests=[Request(required_data={"refresh_token": second_refresh_token, "claims": expected_claims})],
+        responses=[mock_response(json_payload=build_aad_response(access_token=new_token_with_claims))],
+    )
+    credential = SharedTokenCacheCredential(_cache=cache, transport=transport)
+
+    kwargs = {"claims": expected_claims}
+    if get_token_method == "get_token_info":
+        kwargs = {"options": kwargs}
+    token = getattr(credential, get_token_method)(scope, **kwargs)
+
+    # Should receive the new token with claims, not the cached one
+    assert token.token == new_token_with_claims
+    assert token.token != cached_access_token
+
+
 @pytest.mark.parametrize("get_token_method", GET_TOKEN_METHODS)
 def test_multitenant_authentication(get_token_method):
     default_tenant = "organizations"
diff --git a/sdk/identity/azure-identity/tests/test_shared_cache_credential_async.py b/sdk/identity/azure-identity/tests/test_shared_cache_credential_async.py
index d8ce17cf370e..da51952c13bb 100644
--- a/sdk/identity/azure-identity/tests/test_shared_cache_credential_async.py
+++ b/sdk/identity/azure-identity/tests/test_shared_cache_credential_async.py
@@ -24,6 +24,7 @@
 
 from helpers import (
     build_aad_response,
+    build_id_token,
     id_token_claims,
     mock_response,
     get_discovery_response,
@@ -32,6 +33,7 @@
 )
 from helpers_async import async_validating_transport, AsyncMockTransport
 from test_shared_cache_credential import get_account_event, populated_cache
+from azure.identity._constants import DEVELOPER_SIGN_ON_CLIENT_ID
 
 
 def test_supported():
@@ -719,6 +721,72 @@ async def test_initialization_with_cache_options(get_token_method):
         assert mock_cache_loader.call_count == 1
 
 
+@pytest.mark.asyncio
+@pytest.mark.parametrize("get_token_method", GET_TOKEN_METHODS)
+async def test_claims_skips_cached_access_token(get_token_method):
+    """When claims are provided, the credential should skip cached access tokens and request a new one"""
+
+    scope = "scope"
+    expected_claims = '{"access_token": {"nbf": {"essential": true, "value": "1234567890"}}}'
+    cached_access_token = "cached-access-token"
+    first_refresh_token = "first-refresh-token"
+    second_refresh_token = "second-refresh-token"
+
+    username = "user@example.com"
+    uid = "uid"
+    utid = "utid"
+
+    # Set up cache with an access token and refresh token
+    account = get_account_event(username=username, uid=uid, utid=utid, refresh_token=first_refresh_token)
+    cache = TokenCache()
+    cache.add(account)
+
+    # First request without claims - this will cache an access token
+    transport = async_validating_transport(
+        requests=[Request(required_data={"refresh_token": first_refresh_token})],
+        responses=[
+            mock_response(
+                json_payload=build_aad_response(
+                    uid=uid,
+                    utid=utid,
+                    access_token=cached_access_token,
+                    refresh_token=second_refresh_token,
+                    id_token=build_id_token(
+                        aud=DEVELOPER_SIGN_ON_CLIENT_ID, object_id=uid, tenant_id=utid, username=username
+                    ),
+                )
+            )
+        ],
+    )
+    credential = SharedTokenCacheCredential(_cache=cache, transport=transport)
+    token = await getattr(credential, get_token_method)(scope)
+    assert token.token == cached_access_token
+
+    # Verify the access token is now cached - second request without claims should use it
+    credential = SharedTokenCacheCredential(
+        _cache=cache, transport=Mock(send=Mock(side_effect=Exception("should use cached token")))
+    )
+    token = await getattr(credential, get_token_method)(scope)
+    assert token.token == cached_access_token
+
+    # Now request with claims - should bypass the cached access token and use refresh token
+    new_token_with_claims = "new-access-token-with-claims"
+    transport = async_validating_transport(
+        requests=[Request(required_data={"refresh_token": second_refresh_token, "claims": expected_claims})],
+        responses=[mock_response(json_payload=build_aad_response(access_token=new_token_with_claims))],
+    )
+    credential = SharedTokenCacheCredential(_cache=cache, transport=transport)
+
+    kwargs = {"claims": expected_claims}
+    if get_token_method == "get_token_info":
+        kwargs = {"options": kwargs}
+    token = await getattr(credential, get_token_method)(scope, **kwargs)
+
+    # Should receive the new token with claims, not the cached one
+    assert token.token == new_token_with_claims
+    assert token.token != cached_access_token
+
+
 @pytest.mark.asyncio
 @pytest.mark.parametrize("get_token_method", GET_TOKEN_METHODS)
 async def test_multitenant_authentication(get_token_method):