diff --git a/src/api-service/__app__/onefuzzlib/azure/creds.py b/src/api-service/__app__/onefuzzlib/azure/creds.py
index e3669f131..c4bbc92c0 100644
--- a/src/api-service/__app__/onefuzzlib/azure/creds.py
+++ b/src/api-service/__app__/onefuzzlib/azure/creds.py
@@ -3,10 +3,13 @@
 # Copyright (c) Microsoft Corporation.
 # Licensed under the MIT License.
 
+import functools
+import logging
 import os
-from typing import Any, List
+from typing import Any, Callable, List, TypeVar, cast
 from uuid import UUID
 
+from azure.core.exceptions import ClientAuthenticationError
 from azure.graphrbac import GraphRbacManagementClient
 from azure.graphrbac.models import CheckGroupMembershipParameters
 from azure.identity import DefaultAzureCredential
@@ -136,3 +139,48 @@ def get_scaleset_principal_id() -> UUID:
 @cached
 def get_keyvault_client(vault_url: str) -> SecretClient:
     return SecretClient(vault_url=vault_url, credential=DefaultAzureCredential())
+
+
+def clear_azure_client_cache() -> None:
+    # clears the memoization of the Azure clients.
+
+    from .compute import get_compute_client
+    from .containers import get_blob_service
+    from .network_mgmt_client import get_network_client
+    from .storage import get_mgmt_client
+
+    # currently memoization.cache does not project the wrapped function's types.
+    # As a workaround, CI comments out the `cached` wrapper, then runs the type
+    # validation.  This enables calling the wrapper's clear_cache if it's not
+    # disabled.
+    for func in [
+        get_msi,
+        get_identity,
+        get_compute_client,
+        get_blob_service,
+        get_network_client,
+        get_mgmt_client,
+    ]:
+        clear_func = getattr(func, "clear_cache", None)
+        if clear_func is not None:
+            clear_func()
+
+
+T = TypeVar("T", bound=Callable[..., Any])
+
+
+class retry_on_auth_failure:
+    def __call__(self, func: T) -> T:
+        @functools.wraps(func)
+        def decorated(*args, **kwargs):  # type: ignore
+            try:
+                return func(*args, **kwargs)
+            except ClientAuthenticationError as err:
+                logging.warning(
+                    "clearing authentication cache after auth failure: %s", err
+                )
+
+            clear_azure_client_cache()
+            return func(*args, **kwargs)
+
+        return cast(T, decorated)
diff --git a/src/api-service/__app__/onefuzzlib/azure/vmss.py b/src/api-service/__app__/onefuzzlib/azure/vmss.py
index 6269fab03..14cd0f359 100644
--- a/src/api-service/__app__/onefuzzlib/azure/vmss.py
+++ b/src/api-service/__app__/onefuzzlib/azure/vmss.py
@@ -26,10 +26,15 @@ from onefuzztypes.models import Error
 from onefuzztypes.primitives import Region
 
 from .compute import get_compute_client
-from .creds import get_base_resource_group, get_scaleset_identity_resource_path
+from .creds import (
+    get_base_resource_group,
+    get_scaleset_identity_resource_path,
+    retry_on_auth_failure,
+)
 from .image import get_os
 
 
+@retry_on_auth_failure()
 def list_vmss(name: UUID) -> Optional[List[str]]:
     resource_group = get_base_resource_group()
     client = get_compute_client()
@@ -47,6 +52,7 @@ def list_vmss(name: UUID) -> Optional[List[str]]:
     return None
 
 
+@retry_on_auth_failure()
 def delete_vmss(name: UUID) -> bool:
     resource_group = get_base_resource_group()
     compute_client = get_compute_client()
@@ -63,6 +69,7 @@ def delete_vmss(name: UUID) -> bool:
     return bool(response.status() == "Succeeded")
 
 
+@retry_on_auth_failure()
 def get_vmss(name: UUID) -> Optional[Any]:
     resource_group = get_base_resource_group()
     logging.debug("getting vm: %s", name)
@@ -75,6 +82,7 @@ def get_vmss(name: UUID) -> Optional[Any]:
     return None
 
 
+@retry_on_auth_failure()
 def resize_vmss(name: UUID, capacity: int) -> None:
     check_can_update(name)
 
@@ -94,6 +102,7 @@ def resize_vmss(name: UUID, capacity: int) -> None:
         )
 
 
+@retry_on_auth_failure()
 def get_vmss_size(name: UUID) -> Optional[int]:
     vmss = get_vmss(name)
     if vmss is None:
@@ -101,6 +110,7 @@ def get_vmss_size(name: UUID) -> Optional[int]:
     return cast(int, vmss.sku.capacity)
 
 
+@retry_on_auth_failure()
 def list_instance_ids(name: UUID) -> Dict[UUID, str]:
     logging.debug("get instance IDs for scaleset: %s", name)
     resource_group = get_base_resource_group()
@@ -114,10 +124,12 @@ def list_instance_ids(name: UUID) -> Dict[UUID, str]:
             results[UUID(instance.vm_id)] = cast(str, instance.instance_id)
     except (ResourceNotFoundError, CloudError):
         logging.debug("vm does not exist %s", name)
+
     return results
 
 
 @cached(ttl=60)
+@retry_on_auth_failure()
 def get_instance_id(name: UUID, vm_id: UUID) -> Union[str, Error]:
     resource_group = get_base_resource_group()
     logging.info("get instance ID for scaleset node: %s:%s", name, vm_id)
@@ -151,6 +163,7 @@ def check_can_update(name: UUID) -> Any:
     return vmss
 
 
+@retry_on_auth_failure()
 def reimage_vmss_nodes(name: UUID, vm_ids: Set[UUID]) -> Optional[Error]:
     check_can_update(name)
 
@@ -175,6 +188,7 @@ def reimage_vmss_nodes(name: UUID, vm_ids: Set[UUID]) -> Optional[Error]:
     return None
 
 
+@retry_on_auth_failure()
 def delete_vmss_nodes(name: UUID, vm_ids: Set[UUID]) -> Optional[Error]:
     check_can_update(name)
 
@@ -201,6 +215,7 @@ def delete_vmss_nodes(name: UUID, vm_ids: Set[UUID]) -> Optional[Error]:
     return None
 
 
+@retry_on_auth_failure()
 def update_extensions(name: UUID, extensions: List[Any]) -> None:
     check_can_update(name)
 
@@ -215,6 +230,7 @@ def update_extensions(name: UUID, extensions: List[Any]) -> None:
     logging.info("VM extensions updated: %s", name)
 
 
+@retry_on_auth_failure()
 def create_vmss(
     location: Region,
     name: UUID,
@@ -382,6 +398,7 @@ def create_vmss(
 
 
 @cached(ttl=60)
+@retry_on_auth_failure()
 def list_available_skus(location: str) -> List[str]:
     compute_client = get_compute_client()