diff --git a/supervisor/addons/__init__.py b/supervisor/addons/__init__.py
index 1acadd1a7..689dab9ac 100644
--- a/supervisor/addons/__init__.py
+++ b/supervisor/addons/__init__.py
@@ -15,11 +15,11 @@ from ..exceptions import (
     DockerAPIError,
     DockerError,
     DockerNotFound,
-    DockerRequestError,
     HomeAssistantAPIError,
     HostAppArmorError,
 )
 from ..store.addon import AddonStore
+from ..utils import check_exception_chain
 from .addon import Addon
 from .data import AddonsData
 
@@ -102,11 +102,13 @@ class AddonManager(CoreSysAttributes):
         for addon in tasks:
             try:
                 await addon.start()
-            except DockerRequestError:
-                pass
-            except (AddonConfigurationError, DockerAPIError, DockerNotFound):
-                addon.boot = AddonBoot.MANUAL
-                addon.save_persist()
+            except AddonsError as err:
+                # Check if there is an system/user issue
+                if check_exception_chain(
+                    err, (DockerAPIError, DockerNotFound, AddonConfigurationError)
+                ):
+                    addon.boot = AddonBoot.MANUAL
+                    addon.save_persist()
             except Exception as err:  # pylint: disable=broad-except
                 self.sys_capture_exception(err)
             else:
diff --git a/supervisor/utils/__init__.py b/supervisor/utils/__init__.py
index 41df7065a..ff1078100 100644
--- a/supervisor/utils/__init__.py
+++ b/supervisor/utils/__init__.py
@@ -5,7 +5,7 @@ from ipaddress import IPv4Address
 import logging
 import re
 import socket
-from typing import Optional
+from typing import Any, Optional
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -107,3 +107,17 @@ def check_port(address: IPv4Address, port: int) -> bool:
     except OSError:
         pass
     return False
+
+
+def check_exception_chain(err: Exception, object_type: Any) -> bool:
+    """Check if exception chain include sub exception.
+
+    It's not full recursive because we need mostly only access to the latest.
+    """
+    if issubclass(type(err), object_type):
+        return True
+
+    if not err.__context__:
+        return False
+
+    return check_exception_chain(err.__context__, object_type)
diff --git a/tests/utils/test_exception_helper.py b/tests/utils/test_exception_helper.py
new file mode 100644
index 000000000..6e5c14937
--- /dev/null
+++ b/tests/utils/test_exception_helper.py
@@ -0,0 +1,36 @@
+"""Test exception helpers."""
+
+from supervisor.utils import check_exception_chain
+
+
+def test_simple_chain_exception():
+    """Test simple chain of excepiton."""
+
+    try:
+        raise ValueError()
+    except ValueError as err:
+        assert check_exception_chain(err, ValueError)
+
+
+def test_simple_nested_chain_exception():
+    """Test simple nested chain of excepiton."""
+
+    try:
+        try:
+            raise ValueError()
+        except ValueError as err:
+            raise KeyError() from err
+    except KeyError as err:
+        assert check_exception_chain(err, ValueError)
+
+
+def test_list_nested_chain_exception():
+    """Test list nested chain of excepiton."""
+
+    try:
+        try:
+            raise ValueError()
+        except ValueError as err:
+            raise KeyError() from err
+    except KeyError as err:
+        assert check_exception_chain(err, (ValueError, OSError))