diff --git a/core/src/stackit/core/auth_methods/key_auth.py b/core/src/stackit/core/auth_methods/key_auth.py
index 575e76ac..8cd13547 100644
--- a/core/src/stackit/core/auth_methods/key_auth.py
+++ b/core/src/stackit/core/auth_methods/key_auth.py
@@ -42,6 +42,7 @@ class KeyAuth(AuthBase):
     DEFAULT_TOKEN_ENDPOINT = "https://service-account.api.stackit.cloud/token"  # noqa S105 false positive
     TOKEN_EXPIRY_CHECK_INTERVAL = timedelta(seconds=60)
     EXPIRATION_LEEWAY = timedelta(minutes=5)
+    MAX_REFRESH_RETRIES = 3
 
     timeout: Optional[int] = 30
     initial_token: Optional[str]
@@ -73,6 +74,8 @@ def __init__(
 
     def __call__(self, r: Request) -> Request:
         with self.lock:
+            if self.refresh_future is not None and self.refresh_future.done():
+                self.refresh_future.result()
             if self.__is_token_expired(self.access_token):
                 if self.refresh_future is None or self.refresh_future.done():
                     self.refresh_future = self.executor.submit(self.__refresh_token)
@@ -108,13 +111,15 @@ def __fetch_token_from_endpoint(self) -> None:
             self.access_token = response_json["access_token"]
             self.refresh_token = response_json["refresh_token"]
         except requests.RequestException as e:
-            print(f"Initial token fetch failed: {e}")
+            raise requests.RequestException("Initial token fetch failed") from e
 
     def __start_token_refresh_task(self):
         def token_refresh_task():
             while True:
                 time.sleep(self.TOKEN_EXPIRY_CHECK_INTERVAL.total_seconds())
                 with self.lock:
+                    if self.refresh_future is not None and self.refresh_future.done():
+                        self.refresh_future.result()
                     if self.__is_token_expired(self.access_token) and (
                         self.refresh_future is None or self.refresh_future.done()
                     ):
@@ -135,16 +140,19 @@ def __refresh_token(self):
             "refresh_token": self.refresh_token,
         }
 
-        try:
-            response = requests.post(self.token_endpoint, data=body, timeout=self.timeout)
-            response.raise_for_status()
-            response_data = response.json()
-            new_token = response_data.get("access_token")
-            # with self.lock:
-            self.access_token = new_token
-            print("Token successfully refreshed!")
-        except requests.RequestException as e:
-            print(f"Token refresh failed: {e}")
+        last_exception = None
+        for _ in range(self.MAX_REFRESH_RETRIES):
+            try:
+                response = requests.post(self.token_endpoint, data=body, timeout=self.timeout)
+                response.raise_for_status()
+                response_data = response.json()
+                new_token = response_data.get("access_token")
+                self.access_token = new_token
+                return
+            except requests.RequestException as e:
+                last_exception = e
+
+        raise requests.RequestException("Token refresh failed after retries") from last_exception
 
     def __is_token_expired(self, token: str) -> bool:
         try:
diff --git a/core/tests/core/test_auth.py b/core/tests/core/test_auth.py
index e6866f71..6557bdcd 100644
--- a/core/tests/core/test_auth.py
+++ b/core/tests/core/test_auth.py
@@ -2,11 +2,13 @@
 
 import pytest
 import json
+import jwt
+import requests
 from unittest.mock import patch, mock_open, Mock
 
 from requests.auth import HTTPBasicAuth
 
-from stackit.core.auth_methods.key_auth import KeyAuth
+from stackit.core.auth_methods.key_auth import KeyAuth, ServiceAccountKey
 from stackit.core.auth_methods.token_auth import TokenAuth
 from stackit.core.authorization import Authorization
 from stackit.core.configuration import Configuration
@@ -262,3 +264,32 @@ def test_service_account_keyfile_not_found_raises_exception(self):
         config = Configuration(service_account_key_path="/non/existent/path/to/file")
         with pytest.raises(FileNotFoundError):
             Authorization(config)
+
+    def test_token_refresh_fails_after_retries(self, service_account_key_file_json):
+        service_account_key = ServiceAccountKey.model_validate_json(service_account_key_file_json)
+        service_account_key.credentials.private_key = "test-private-key"
+
+        def set_initial_token(auth):
+            auth.initial_token = "test-initial-token"
+
+        with patch.object(KeyAuth, "_KeyAuth__create_initial_token", new=set_initial_token), patch.object(
+            KeyAuth, "_KeyAuth__start_token_refresh_task", return_value=None
+        ), patch("requests.post") as mock_post:
+            init_response = Mock()
+            init_response.raise_for_status.return_value = None
+            init_response.json.return_value = {
+                "access_token": jwt.encode({"exp": 4102444800}, "secret", algorithm="HS256"),
+                "refresh_token": jwt.encode({"exp": 4102444800}, "secret", algorithm="HS256"),
+            }
+            mock_post.return_value = init_response
+
+            auth = KeyAuth(service_account_key)
+            auth.refresh_token = jwt.encode({"exp": 4102444800}, "secret", algorithm="HS256")
+
+            mock_post.reset_mock()
+            mock_post.side_effect = requests.RequestException("refresh failed")
+
+            with pytest.raises(requests.RequestException):
+                auth._KeyAuth__refresh_token()
+
+            assert mock_post.call_count == KeyAuth.MAX_REFRESH_RETRIES