diff --git a/supervisor/addons/__init__.py b/supervisor/addons/__init__.py
index 6efb4a52f..357acf647 100644
--- a/supervisor/addons/__init__.py
+++ b/supervisor/addons/__init__.py
@@ -23,6 +23,7 @@ from ..jobs.decorator import Job, JobCondition
 from ..resolution.const import ContextType, IssueType, SuggestionType
 from ..store.addon import AddonStore
 from ..utils import check_exception_chain
+from ..utils.sentry import capture_exception
 from .addon import Addon
 from .const import ADDON_UPDATE_CONDITIONS
 from .data import AddonsData
@@ -114,7 +115,7 @@ class AddonManager(CoreSysAttributes):
                     addon.boot = AddonBoot.MANUAL
                     addon.save_persist()
             except Exception as err:  # pylint: disable=broad-except
-                self.sys_capture_exception(err)
+                capture_exception(err)
             else:
                 continue
 
@@ -142,7 +143,7 @@ class AddonManager(CoreSysAttributes):
                 await addon.stop()
             except Exception as err:  # pylint: disable=broad-except
                 _LOGGER.warning("Can't stop Add-on %s: %s", addon.slug, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
     @Job(
         conditions=ADDON_UPDATE_CONDITIONS,
@@ -421,7 +422,7 @@ class AddonManager(CoreSysAttributes):
                     reference=addon.slug,
                     suggestions=[SuggestionType.EXECUTE_REPAIR],
                 )
-                self.sys_capture_exception(err)
+                capture_exception(err)
             else:
                 self.sys_plugins.dns.add_host(
                     ipv4=addon.ip_address, names=[addon.hostname], write=False
diff --git a/supervisor/api/const.py b/supervisor/api/const.py
index c2efcfd26..6a444261c 100644
--- a/supervisor/api/const.py
+++ b/supervisor/api/const.py
@@ -9,9 +9,6 @@ CONTENT_TYPE_URL = "application/x-www-form-urlencoded"
 
 COOKIE_INGRESS = "ingress_session"
 
-HEADER_TOKEN_OLD = "X-Hassio-Key"
-HEADER_TOKEN = "X-Supervisor-Token"
-
 ATTR_APPARMOR_VERSION = "apparmor_version"
 ATTR_AGENT_VERSION = "agent_version"
 ATTR_AVAILABLE_UPDATES = "available_updates"
diff --git a/supervisor/api/ingress.py b/supervisor/api/ingress.py
index 74df1a8ac..2e13b2b82 100644
--- a/supervisor/api/ingress.py
+++ b/supervisor/api/ingress.py
@@ -22,9 +22,11 @@ from ..const import (
     ATTR_PANELS,
     ATTR_SESSION,
     ATTR_TITLE,
+    HEADER_TOKEN,
+    HEADER_TOKEN_OLD,
 )
 from ..coresys import CoreSysAttributes
-from .const import COOKIE_INGRESS, HEADER_TOKEN, HEADER_TOKEN_OLD
+from .const import COOKIE_INGRESS
 from .utils import api_process, api_validate, require_home_assistant
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
diff --git a/supervisor/api/supervisor.py b/supervisor/api/supervisor.py
index 64592b4bd..7d3a3e45c 100644
--- a/supervisor/api/supervisor.py
+++ b/supervisor/api/supervisor.py
@@ -46,6 +46,7 @@ from ..const import (
 from ..coresys import CoreSysAttributes
 from ..exceptions import APIError
 from ..store.validate import repositories
+from ..utils.sentry import close_sentry, init_sentry
 from ..utils.validate import validate_timezone
 from ..validate import version_tag, wait_boot
 from .const import CONTENT_TYPE_BINARY
@@ -144,6 +145,11 @@ class APISupervisor(CoreSysAttributes):
             self.sys_config.diagnostics = body[ATTR_DIAGNOSTICS]
             self.sys_dbus.agent.diagnostics = body[ATTR_DIAGNOSTICS]
 
+            if body[ATTR_DIAGNOSTICS]:
+                init_sentry(self.coresys)
+            else:
+                close_sentry()
+
         if ATTR_LOGGING in body:
             self.sys_config.logging = body[ATTR_LOGGING]
 
diff --git a/supervisor/api/utils.py b/supervisor/api/utils.py
index ccd23f6bc..aa94fc402 100644
--- a/supervisor/api/utils.py
+++ b/supervisor/api/utils.py
@@ -10,6 +10,8 @@ import voluptuous as vol
 from voluptuous.humanize import humanize_error
 
 from ..const import (
+    HEADER_TOKEN,
+    HEADER_TOKEN_OLD,
     JSON_DATA,
     JSON_MESSAGE,
     JSON_RESULT,
@@ -22,7 +24,7 @@ from ..exceptions import APIError, APIForbidden, DockerAPIError, HassioError
 from ..utils import check_exception_chain, get_message_from_exception_chain
 from ..utils.json import JSONEncoder
 from ..utils.log_format import format_message
-from .const import CONTENT_TYPE_BINARY, HEADER_TOKEN, HEADER_TOKEN_OLD
+from .const import CONTENT_TYPE_BINARY
 
 
 def excract_supervisor_token(request: web.Request) -> str | None:
diff --git a/supervisor/backups/manager.py b/supervisor/backups/manager.py
index 5c82b2f78..73d3fb810 100644
--- a/supervisor/backups/manager.py
+++ b/supervisor/backups/manager.py
@@ -17,6 +17,7 @@ from ..exceptions import AddonsError
 from ..jobs.decorator import Job, JobCondition
 from ..utils.common import FileConfiguration
 from ..utils.dt import utcnow
+from ..utils.sentry import capture_exception
 from .backup import Backup
 from .const import BackupType
 from .utils import create_slug
@@ -172,7 +173,7 @@ class BackupManager(FileConfiguration, CoreSysAttributes):
 
         except Exception as err:  # pylint: disable=broad-except
             _LOGGER.exception("Backup %s error", backup.slug)
-            self.sys_capture_exception(err)
+            capture_exception(err)
             return None
         else:
             self._backups[backup.slug] = backup
@@ -296,7 +297,7 @@ class BackupManager(FileConfiguration, CoreSysAttributes):
 
         except Exception as err:  # pylint: disable=broad-except
             _LOGGER.exception("Restore %s error", backup.slug)
-            self.sys_capture_exception(err)
+            capture_exception(err)
             return False
         else:
             return True
diff --git a/supervisor/bootstrap.py b/supervisor/bootstrap.py
index 8fc02aa9e..67389ab35 100644
--- a/supervisor/bootstrap.py
+++ b/supervisor/bootstrap.py
@@ -5,13 +5,6 @@ from pathlib import Path
 import signal
 
 from colorlog import ColoredFormatter
-import sentry_sdk
-from sentry_sdk.integrations.aiohttp import AioHttpIntegration
-from sentry_sdk.integrations.atexit import AtexitIntegration
-from sentry_sdk.integrations.dedupe import DedupeIntegration
-from sentry_sdk.integrations.excepthook import ExcepthookIntegration
-from sentry_sdk.integrations.logging import LoggingIntegration
-from sentry_sdk.integrations.threading import ThreadingIntegration
 
 from .addons import AddonManager
 from .api import RestAPI
@@ -28,7 +21,6 @@ from .const import (
     ENV_SUPERVISOR_SHARE,
     MACHINE_ID,
     SOCKET_DOCKER,
-    SUPERVISOR_VERSION,
     LogLevel,
     UpdateChannel,
 )
@@ -42,7 +34,6 @@ from .homeassistant.module import HomeAssistant
 from .host.manager import HostManager
 from .ingress import Ingress
 from .jobs import JobManager
-from .misc.filter import filter_data
 from .misc.scheduler import Scheduler
 from .misc.tasks import Tasks
 from .os.manager import OSManager
@@ -54,6 +45,7 @@ from .store import StoreManager
 from .store.validate import ensure_builtin_repositories
 from .supervisor import Supervisor
 from .updater import Updater
+from .utils.sentry import init_sentry
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -90,7 +82,8 @@ async def initialize_coresys() -> CoreSys:
     coresys.bus = Bus(coresys)
 
     # diagnostics
-    setup_diagnostics(coresys)
+    if coresys.config.diagnostics:
+        init_sentry(coresys)
 
     # bootstrap config
     initialize_system(coresys)
@@ -316,25 +309,3 @@ def supervisor_debugger(coresys: CoreSys) -> None:
     if coresys.config.debug_block:
         _LOGGER.info("Wait until debugger is attached")
         debugpy.wait_for_client()
-
-
-def setup_diagnostics(coresys: CoreSys) -> None:
-    """Sentry diagnostic backend."""
-    _LOGGER.info("Initializing Supervisor Sentry")
-    # pylint: disable=abstract-class-instantiated
-    sentry_sdk.init(
-        dsn="https://9c6ea70f49234442b4746e447b24747e@o427061.ingest.sentry.io/5370612",
-        before_send=lambda event, hint: filter_data(coresys, event, hint),
-        auto_enabling_integrations=False,
-        default_integrations=False,
-        integrations=[
-            AioHttpIntegration(),
-            ExcepthookIntegration(),
-            DedupeIntegration(),
-            AtexitIntegration(),
-            ThreadingIntegration(),
-            LoggingIntegration(level=logging.WARNING, event_level=logging.CRITICAL),
-        ],
-        release=SUPERVISOR_VERSION,
-        max_breadcrumbs=30,
-    )
diff --git a/supervisor/const.py b/supervisor/const.py
index a515f8495..346108707 100644
--- a/supervisor/const.py
+++ b/supervisor/const.py
@@ -69,6 +69,9 @@ JSON_RESULT = "result"
 RESULT_ERROR = "error"
 RESULT_OK = "ok"
 
+HEADER_TOKEN_OLD = "X-Hassio-Key"
+HEADER_TOKEN = "X-Supervisor-Token"
+
 ENV_HOMEASSISTANT_REPOSITORY = "HOMEASSISTANT_REPOSITORY"
 ENV_SUPERVISOR_DEV = "SUPERVISOR_DEV"
 ENV_SUPERVISOR_MACHINE = "SUPERVISOR_MACHINE"
diff --git a/supervisor/core.py b/supervisor/core.py
index 8f56f6b2f..2b211e405 100644
--- a/supervisor/core.py
+++ b/supervisor/core.py
@@ -20,6 +20,7 @@ from .exceptions import (
 from .homeassistant.core import LANDINGPAGE
 from .resolution.const import ContextType, IssueType, SuggestionType, UnhealthyReason
 from .utils.dt import utcnow
+from .utils.sentry import capture_exception
 from .utils.whoami import retrieve_whoami
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
@@ -153,7 +154,7 @@ class Core(CoreSysAttributes):
                     "Fatal error happening on load Task %s: %s", setup_task, err
                 )
                 self.sys_resolution.unhealthy = UnhealthyReason.SETUP
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         # Set OS Agent diagnostics if needed
         if (
@@ -196,7 +197,7 @@ class Core(CoreSysAttributes):
                     "future versions of Home Assistant!"
                 )
                 self.sys_resolution.unhealthy = UnhealthyReason.SUPERVISOR
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         # Start addon mark as initialize
         await self.sys_addons.boot(AddonStartup.INITIALIZE)
@@ -226,12 +227,12 @@ class Core(CoreSysAttributes):
                     await self.sys_homeassistant.core.start()
                 except HomeAssistantCrashError as err:
                     _LOGGER.error("Can't start Home Assistant Core - rebuiling")
-                    self.sys_capture_exception(err)
+                    capture_exception(err)
 
                     with suppress(HomeAssistantError):
                         await self.sys_homeassistant.core.rebuild()
                 except HomeAssistantError as err:
-                    self.sys_capture_exception(err)
+                    capture_exception(err)
             else:
                 _LOGGER.info("Skiping start of Home Assistant")
 
diff --git a/supervisor/coresys.py b/supervisor/coresys.py
index 4456825e2..67e0efe06 100644
--- a/supervisor/coresys.py
+++ b/supervisor/coresys.py
@@ -10,7 +10,6 @@ from types import MappingProxyType
 from typing import TYPE_CHECKING, Any, TypeVar
 
 import aiohttp
-import sentry_sdk
 
 from .config import CoreConfig
 from .const import ENV_SUPERVISOR_DEV, SERVER_SOFTWARE
@@ -514,10 +513,6 @@ class CoreSys:
         """Create an async task."""
         return self.loop.create_task(coroutine)
 
-    def capture_exception(self, err: Exception) -> None:
-        """Capture a exception."""
-        sentry_sdk.capture_exception(err)
-
 
 class CoreSysAttributes:
     """Inherit basic CoreSysAttributes."""
@@ -692,7 +687,3 @@ class CoreSysAttributes:
     def sys_create_task(self, coroutine: Coroutine) -> asyncio.Task:
         """Create an async task."""
         return self.coresys.create_task(coroutine)
-
-    def sys_capture_exception(self, err: Exception) -> None:
-        """Capture a exception."""
-        self.coresys.capture_exception(err)
diff --git a/supervisor/dbus/network/__init__.py b/supervisor/dbus/network/__init__.py
index eadbcf4bb..cf6310858 100644
--- a/supervisor/dbus/network/__init__.py
+++ b/supervisor/dbus/network/__init__.py
@@ -4,7 +4,6 @@ from typing import Any
 
 from awesomeversion import AwesomeVersion, AwesomeVersionException
 from dbus_fast.aio.message_bus import MessageBus
-import sentry_sdk
 
 from ...exceptions import (
     DBusError,
@@ -12,6 +11,7 @@ from ...exceptions import (
     DBusInterfaceError,
     HostNotSupportedError,
 )
+from ...utils.sentry import capture_exception
 from ..const import (
     DBUS_ATTR_CONNECTION_ENABLED,
     DBUS_ATTR_DEVICES,
@@ -194,7 +194,7 @@ class NetworkManager(DBusInterfaceProxy):
                     continue
                 except Exception as err:  # pylint: disable=broad-except
                     _LOGGER.exception("Error while processing %s: %s", device, err)
-                    sentry_sdk.capture_exception(err)
+                    capture_exception(err)
                     continue
 
             # Skeep interface
diff --git a/supervisor/docker/addon.py b/supervisor/docker/addon.py
index 7070ffe93..00a4fc087 100644
--- a/supervisor/docker/addon.py
+++ b/supervisor/docker/addon.py
@@ -44,6 +44,7 @@ from ..hardware.data import Device
 from ..jobs.decorator import Job, JobCondition, JobExecutionLimit
 from ..resolution.const import ContextType, IssueType, SuggestionType
 from ..utils import process_lock
+from ..utils.sentry import capture_exception
 from .const import (
     DBUS_PATH,
     DBUS_VOLUME,
@@ -516,7 +517,7 @@ class DockerAddon(DockerInterface):
             )
         except CoreDNSError as err:
             _LOGGER.warning("Can't update DNS for %s", self.name)
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
         # Hardware Access
         if self.addon.static_devices:
@@ -699,7 +700,7 @@ class DockerAddon(DockerInterface):
                 self.sys_plugins.dns.delete_host(self.addon.hostname)
             except CoreDNSError as err:
                 _LOGGER.warning("Can't update DNS for %s", self.name)
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         # Hardware
         if self._hw_listener:
diff --git a/supervisor/docker/interface.py b/supervisor/docker/interface.py
index 6d48b1583..b75edd11f 100644
--- a/supervisor/docker/interface.py
+++ b/supervisor/docker/interface.py
@@ -36,6 +36,7 @@ from ..exceptions import (
 )
 from ..resolution.const import ContextType, IssueType, SuggestionType
 from ..utils import process_lock
+from ..utils.sentry import capture_exception
 from .const import ContainerState, RestartPolicy
 from .manager import CommandReturn
 from .monitor import DockerContainerStateEvent
@@ -259,7 +260,7 @@ class DockerInterface(CoreSysAttributes):
                 f"Can't install {image}:{version!s}: {err}", _LOGGER.error
             ) from err
         except (docker.errors.DockerException, requests.RequestException) as err:
-            self.sys_capture_exception(err)
+            capture_exception(err)
             raise DockerError(
                 f"Unknown error with {image}:{version!s} -> {err!s}", _LOGGER.error
             ) from err
diff --git a/supervisor/homeassistant/core.py b/supervisor/homeassistant/core.py
index 1eb7d3b8f..2905820cb 100644
--- a/supervisor/homeassistant/core.py
+++ b/supervisor/homeassistant/core.py
@@ -27,6 +27,7 @@ from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job, JobCondition
 from ..resolution.const import ContextType, IssueType
 from ..utils import convert_to_ascii, process_lock
+from ..utils.sentry import capture_exception
 from .const import (
     LANDINGPAGE,
     WATCHDOG_MAX_ATTEMPTS,
@@ -125,16 +126,18 @@ class HomeAssistantCore(CoreSysAttributes):
                 await self.instance.install(
                     LANDINGPAGE, image=self.sys_updater.image_homeassistant
                 )
-            except DockerError:
-                _LOGGER.warning("Fails install landingpage, retry after 30sec")
-                await asyncio.sleep(30)
-            except Exception as err:  # pylint: disable=broad-except
-                self.sys_capture_exception(err)
-            else:
-                self.sys_homeassistant.version = LANDINGPAGE
-                self.sys_homeassistant.image = self.sys_updater.image_homeassistant
-                self.sys_homeassistant.save_data()
                 break
+            except DockerError:
+                pass
+            except Exception as err:  # pylint: disable=broad-except
+                capture_exception(err)
+
+            _LOGGER.warning("Fails install landingpage, retry after 30sec")
+            await asyncio.sleep(30)
+
+        self.sys_homeassistant.version = LANDINGPAGE
+        self.sys_homeassistant.image = self.sys_updater.image_homeassistant
+        self.sys_homeassistant.save_data()
 
     @process_lock
     async def install(self) -> None:
@@ -155,7 +158,7 @@ class HomeAssistantCore(CoreSysAttributes):
                 except DockerError:
                     pass
                 except Exception as err:  # pylint: disable=broad-except
-                    self.sys_capture_exception(err)
+                    capture_exception(err)
 
             _LOGGER.warning("Error on Home Assistant installation. Retry in 30sec")
             await asyncio.sleep(30)
@@ -473,7 +476,7 @@ class HomeAssistantCore(CoreSysAttributes):
                     try:
                         await self.start()
                     except HomeAssistantError as err:
-                        self.sys_capture_exception(err)
+                        capture_exception(err)
                     else:
                         break
 
@@ -485,7 +488,7 @@ class HomeAssistantCore(CoreSysAttributes):
                 except HomeAssistantError as err:
                     attempts = attempts + 1
                     _LOGGER.error("Watchdog restart of Home Assistant failed!")
-                    self.sys_capture_exception(err)
+                    capture_exception(err)
                 else:
                     break
 
diff --git a/supervisor/jobs/decorator.py b/supervisor/jobs/decorator.py
index ac7bf38ca..3acb73c44 100644
--- a/supervisor/jobs/decorator.py
+++ b/supervisor/jobs/decorator.py
@@ -6,13 +6,12 @@ from functools import wraps
 import logging
 from typing import Any
 
-import sentry_sdk
-
 from ..const import CoreState
 from ..coresys import CoreSys, CoreSysAttributes
 from ..exceptions import HassioError, JobConditionException, JobException
 from ..host.const import HostFeature
 from ..resolution.const import MINIMUM_FREE_SPACE_THRESHOLD, ContextType, IssueType
+from ..utils.sentry import capture_exception
 from .const import JobCondition, JobExecutionLimit
 
 _LOGGER: logging.Logger = logging.getLogger(__package__)
@@ -157,7 +156,7 @@ class Job(CoreSysAttributes):
                 raise err
             except Exception as err:
                 _LOGGER.exception("Unhandled exception: %s", err)
-                sentry_sdk.capture_exception(err)
+                capture_exception(err)
                 raise JobException() from err
             finally:
                 if self.cleanup:
diff --git a/supervisor/misc/filter.py b/supervisor/misc/filter.py
index 81057aa22..14ff3fe40 100644
--- a/supervisor/misc/filter.py
+++ b/supervisor/misc/filter.py
@@ -5,8 +5,7 @@ import re
 from aiohttp import hdrs
 import attr
 
-from ..api.const import HEADER_TOKEN, HEADER_TOKEN_OLD
-from ..const import CoreState
+from ..const import HEADER_TOKEN, HEADER_TOKEN_OLD, CoreState
 from ..coresys import CoreSys
 from ..exceptions import AddonConfigurationError
 
diff --git a/supervisor/misc/tasks.py b/supervisor/misc/tasks.py
index 3c18f7649..52327644b 100644
--- a/supervisor/misc/tasks.py
+++ b/supervisor/misc/tasks.py
@@ -7,6 +7,7 @@ from ..coresys import CoreSysAttributes
 from ..exceptions import AddonsError, HomeAssistantError, ObserverError
 from ..jobs.decorator import Job, JobCondition
 from ..plugins.const import PLUGIN_UPDATE_CONDITIONS
+from ..utils.sentry import capture_exception
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -159,7 +160,7 @@ class Tasks(CoreSysAttributes):
             await self.sys_homeassistant.core.restart()
         except HomeAssistantError as err:
             _LOGGER.error("Home Assistant watchdog reanimation failed!")
-            self.sys_capture_exception(err)
+            capture_exception(err)
         finally:
             self._cache[HASS_WATCHDOG_API] = 0
 
@@ -265,7 +266,7 @@ class Tasks(CoreSysAttributes):
                 await addon.restart()
             except AddonsError as err:
                 _LOGGER.error("%s watchdog reanimation failed with %s", addon.slug, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
             finally:
                 self._cache[addon.slug] = 0
 
diff --git a/supervisor/plugins/audio.py b/supervisor/plugins/audio.py
index 692ee03a7..98170a62d 100644
--- a/supervisor/plugins/audio.py
+++ b/supervisor/plugins/audio.py
@@ -26,6 +26,7 @@ from ..exceptions import (
 from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job
 from ..utils.json import write_json_file
+from ..utils.sentry import capture_exception
 from .base import PluginBase
 from .const import (
     FILE_HASSIO_AUDIO,
@@ -188,7 +189,7 @@ class PluginAudio(PluginBase):
             await self.instance.install(self.version)
         except DockerError as err:
             _LOGGER.error("Repair of Audio failed")
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
     def pulse_client(self, input_profile=None, output_profile=None) -> str:
         """Generate an /etc/pulse/client.conf data."""
diff --git a/supervisor/plugins/base.py b/supervisor/plugins/base.py
index 2b8d2ed49..7237974df 100644
--- a/supervisor/plugins/base.py
+++ b/supervisor/plugins/base.py
@@ -14,6 +14,7 @@ from ..docker.interface import DockerInterface
 from ..docker.monitor import DockerContainerStateEvent
 from ..exceptions import DockerError, PluginError
 from ..utils.common import FileConfiguration
+from ..utils.sentry import capture_exception
 from .const import WATCHDOG_MAX_ATTEMPTS, WATCHDOG_RETRY_SECONDS
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
@@ -129,7 +130,7 @@ class PluginBase(ABC, FileConfiguration, CoreSysAttributes):
                 except PluginError as err:
                     attempts = attempts + 1
                     _LOGGER.error("Watchdog restart of %s plugin failed!", self.slug)
-                    self.sys_capture_exception(err)
+                    capture_exception(err)
                 else:
                     break
 
diff --git a/supervisor/plugins/cli.py b/supervisor/plugins/cli.py
index c9015e057..b4baec56c 100644
--- a/supervisor/plugins/cli.py
+++ b/supervisor/plugins/cli.py
@@ -18,6 +18,7 @@ from ..docker.stats import DockerStats
 from ..exceptions import CliError, CliJobError, CliUpdateError, DockerError
 from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job
+from ..utils.sentry import capture_exception
 from .base import PluginBase
 from .const import (
     FILE_HASSIO_CLI,
@@ -147,7 +148,7 @@ class PluginCli(PluginBase):
             await self.instance.install(self.version)
         except DockerError as err:
             _LOGGER.error("Repair of HA cli failed")
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
     @Job(
         limit=JobExecutionLimit.THROTTLE_RATE_LIMIT,
diff --git a/supervisor/plugins/dns.py b/supervisor/plugins/dns.py
index b73faa9f5..e6c13e87d 100644
--- a/supervisor/plugins/dns.py
+++ b/supervisor/plugins/dns.py
@@ -31,6 +31,7 @@ from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job
 from ..resolution.const import ContextType, IssueType, SuggestionType
 from ..utils.json import write_json_file
+from ..utils.sentry import capture_exception
 from ..validate import dns_url
 from .base import PluginBase
 from .const import (
@@ -421,7 +422,7 @@ class PluginDns(PluginBase):
             await self.instance.install(self.version)
         except DockerError as err:
             _LOGGER.error("Repair of CoreDNS failed")
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
     def _write_resolv(self, resolv_conf: Path) -> None:
         """Update/Write resolv.conf file."""
diff --git a/supervisor/plugins/manager.py b/supervisor/plugins/manager.py
index 732b0689d..fa6bd7f00 100644
--- a/supervisor/plugins/manager.py
+++ b/supervisor/plugins/manager.py
@@ -5,6 +5,7 @@ import logging
 from ..coresys import CoreSys, CoreSysAttributes
 from ..exceptions import HassioError
 from ..resolution.const import ContextType, IssueType, SuggestionType
+from ..utils.sentry import capture_exception
 from .audio import PluginAudio
 from .base import PluginBase
 from .cli import PluginCli
@@ -72,7 +73,7 @@ class PluginManager(CoreSysAttributes):
                     reference=plugin.slug,
                     suggestions=[SuggestionType.EXECUTE_REPAIR],
                 )
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         # Check requirements
         await self.sys_updater.reload()
@@ -102,7 +103,7 @@ class PluginManager(CoreSysAttributes):
                 )
             except Exception as err:  # pylint: disable=broad-except
                 _LOGGER.warning("Can't update plugin %s: %s", plugin.slug, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
     async def repair(self) -> None:
         """Repair Supervisor plugins."""
@@ -118,4 +119,4 @@ class PluginManager(CoreSysAttributes):
                 await plugin.stop()
             except Exception as err:  # pylint: disable=broad-except
                 _LOGGER.warning("Can't stop plugin %s: %s", plugin.slug, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
diff --git a/supervisor/plugins/multicast.py b/supervisor/plugins/multicast.py
index aa335bd16..68ba79958 100644
--- a/supervisor/plugins/multicast.py
+++ b/supervisor/plugins/multicast.py
@@ -20,6 +20,7 @@ from ..exceptions import (
 )
 from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job
+from ..utils.sentry import capture_exception
 from .base import PluginBase
 from .const import (
     FILE_HASSIO_MULTICAST,
@@ -142,7 +143,7 @@ class PluginMulticast(PluginBase):
             await self.instance.install(self.version)
         except DockerError as err:
             _LOGGER.error("Repair of Multicast failed")
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
     @Job(
         limit=JobExecutionLimit.THROTTLE_RATE_LIMIT,
diff --git a/supervisor/plugins/observer.py b/supervisor/plugins/observer.py
index 171eb3570..e1e1be065 100644
--- a/supervisor/plugins/observer.py
+++ b/supervisor/plugins/observer.py
@@ -23,6 +23,7 @@ from ..exceptions import (
 )
 from ..jobs.const import JobExecutionLimit
 from ..jobs.decorator import Job
+from ..utils.sentry import capture_exception
 from .base import PluginBase
 from .const import (
     FILE_HASSIO_OBSERVER,
@@ -152,7 +153,7 @@ class PluginObserver(PluginBase):
             await self.instance.install(self.version)
         except DockerError as err:
             _LOGGER.error("Repair of HA observer failed")
-            self.sys_capture_exception(err)
+            capture_exception(err)
 
     @Job(
         limit=JobExecutionLimit.THROTTLE_RATE_LIMIT,
diff --git a/supervisor/resolution/check.py b/supervisor/resolution/check.py
index d1bad2b78..c9f5e7f60 100644
--- a/supervisor/resolution/check.py
+++ b/supervisor/resolution/check.py
@@ -6,6 +6,7 @@ from typing import Any
 from ..const import ATTR_CHECKS
 from ..coresys import CoreSys, CoreSysAttributes
 from ..exceptions import ResolutionNotFound
+from ..utils.sentry import capture_exception
 from .checks.base import CheckBase
 from .validate import get_valid_modules
 
@@ -59,6 +60,6 @@ class ResolutionCheck(CoreSysAttributes):
                 await check()
             except Exception as err:  # pylint: disable=broad-except
                 _LOGGER.error("Error during processing %s: %s", check.issue, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         _LOGGER.info("System checks complete")
diff --git a/supervisor/resolution/checks/dns_server.py b/supervisor/resolution/checks/dns_server.py
index 47e785c4a..c88e4b2e9 100644
--- a/supervisor/resolution/checks/dns_server.py
+++ b/supervisor/resolution/checks/dns_server.py
@@ -9,6 +9,7 @@ from ...const import CoreState
 from ...coresys import CoreSys
 from ...jobs.const import JobCondition, JobExecutionLimit
 from ...jobs.decorator import Job
+from ...utils.sentry import capture_exception
 from ..const import DNS_CHECK_HOST, ContextType, IssueType
 from .base import CheckBase
 
@@ -39,7 +40,7 @@ class CheckDNSServer(CheckBase):
                 ContextType.DNS_SERVER,
                 reference=dns_servers[i],
             )
-            self.sys_capture_exception(results[i])
+            capture_exception(results[i])
 
     @Job(conditions=[JobCondition.INTERNET_SYSTEM])
     async def approve_check(self, reference: str | None = None) -> bool:
diff --git a/supervisor/resolution/checks/dns_server_ipv6.py b/supervisor/resolution/checks/dns_server_ipv6.py
index 95b1d43c1..13657021d 100644
--- a/supervisor/resolution/checks/dns_server_ipv6.py
+++ b/supervisor/resolution/checks/dns_server_ipv6.py
@@ -9,6 +9,7 @@ from ...const import CoreState
 from ...coresys import CoreSys
 from ...jobs.const import JobCondition, JobExecutionLimit
 from ...jobs.decorator import Job
+from ...utils.sentry import capture_exception
 from ..const import DNS_CHECK_HOST, DNS_ERROR_NO_DATA, ContextType, IssueType
 from .base import CheckBase
 
@@ -44,7 +45,7 @@ class CheckDNSServerIPv6(CheckBase):
                 ContextType.DNS_SERVER,
                 reference=dns_servers[i],
             )
-            self.sys_capture_exception(results[i])
+            capture_exception(results[i])
 
     @Job(conditions=[JobCondition.INTERNET_SYSTEM])
     async def approve_check(self, reference: str | None = None) -> bool:
diff --git a/supervisor/resolution/evaluate.py b/supervisor/resolution/evaluate.py
index b510a8b22..8c190ce31 100644
--- a/supervisor/resolution/evaluate.py
+++ b/supervisor/resolution/evaluate.py
@@ -4,6 +4,7 @@ import logging
 
 from ..coresys import CoreSys, CoreSysAttributes
 from ..exceptions import ResolutionNotFound
+from ..utils.sentry import capture_exception
 from .const import UnhealthyReason, UnsupportedReason
 from .evaluations.base import EvaluateBase
 from .validate import get_valid_modules
@@ -59,7 +60,7 @@ class ResolutionEvaluation(CoreSysAttributes):
                 _LOGGER.warning(
                     "Error during processing %s: %s", evaluation.reason, err
                 )
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         if any(reason in self.sys_resolution.unsupported for reason in UNHEALTHY):
             self.sys_resolution.unhealthy = UnhealthyReason.DOCKER
diff --git a/supervisor/resolution/fixup.py b/supervisor/resolution/fixup.py
index b567a3f78..1d34703e4 100644
--- a/supervisor/resolution/fixup.py
+++ b/supervisor/resolution/fixup.py
@@ -5,6 +5,7 @@ import logging
 from ..coresys import CoreSys, CoreSysAttributes
 from ..jobs.const import JobCondition
 from ..jobs.decorator import Job
+from ..utils.sentry import capture_exception
 from .data import Issue, Suggestion
 from .fixups.base import FixupBase
 from .validate import get_valid_modules
@@ -47,7 +48,7 @@ class ResolutionFixup(CoreSysAttributes):
                 await fix()
             except Exception as err:  # pylint: disable=broad-except
                 _LOGGER.warning("Error during processing %s: %s", fix.suggestion, err)
-                self.sys_capture_exception(err)
+                capture_exception(err)
 
         _LOGGER.info("System autofix complete")
 
diff --git a/supervisor/supervisor.py b/supervisor/supervisor.py
index 9a863466f..974d7a42a 100644
--- a/supervisor/supervisor.py
+++ b/supervisor/supervisor.py
@@ -30,6 +30,7 @@ from .jobs.const import JobCondition, JobExecutionLimit
 from .jobs.decorator import Job
 from .resolution.const import ContextType, IssueType
 from .utils.codenotary import calc_checksum
+from .utils.sentry import capture_exception
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -199,7 +200,7 @@ class Supervisor(CoreSysAttributes):
             self.sys_resolution.create_issue(
                 IssueType.UPDATE_FAILED, ContextType.SUPERVISOR
             )
-            self.sys_capture_exception(err)
+            capture_exception(err)
             raise SupervisorUpdateError(
                 f"Update of Supervisor failed: {err!s}", _LOGGER.error
             ) from err
diff --git a/supervisor/utils/log_format.py b/supervisor/utils/log_format.py
index d5f439acb..65b0cf198 100644
--- a/supervisor/utils/log_format.py
+++ b/supervisor/utils/log_format.py
@@ -2,7 +2,7 @@
 import logging
 import re
 
-import sentry_sdk
+from .sentry import capture_exception
 
 _LOGGER: logging.Logger = logging.getLogger(__name__)
 
@@ -19,6 +19,6 @@ def format_message(message: str) -> str:
             return f"Port '{match.group(1)}' is already in use by something else on the host."
     except TypeError as err:
         _LOGGER.error("The type of message is not a string - %s", err)
-        sentry_sdk.capture_exception(err)
+        capture_exception(err)
 
     return message
diff --git a/supervisor/utils/sentry.py b/supervisor/utils/sentry.py
new file mode 100644
index 000000000..f1c303a31
--- /dev/null
+++ b/supervisor/utils/sentry.py
@@ -0,0 +1,60 @@
+"""Utilities for sentry."""
+
+import logging
+
+import sentry_sdk
+from sentry_sdk.integrations.aiohttp import AioHttpIntegration
+from sentry_sdk.integrations.atexit import AtexitIntegration
+from sentry_sdk.integrations.dedupe import DedupeIntegration
+from sentry_sdk.integrations.excepthook import ExcepthookIntegration
+from sentry_sdk.integrations.logging import LoggingIntegration
+from sentry_sdk.integrations.threading import ThreadingIntegration
+
+from ..const import SUPERVISOR_VERSION
+from ..coresys import CoreSys
+from ..misc.filter import filter_data
+
+_LOGGER: logging.Logger = logging.getLogger(__name__)
+
+
+def sentry_connected() -> bool:
+    """Is sentry connected."""
+    return sentry_sdk.Hub.current.client and sentry_sdk.Hub.current.client.transport
+
+
+def init_sentry(coresys: CoreSys) -> None:
+    """Initialize sentry client."""
+    if not sentry_connected():
+        _LOGGER.info("Initializing Supervisor Sentry")
+        sentry_sdk.init(
+            dsn="https://9c6ea70f49234442b4746e447b24747e@o427061.ingest.sentry.io/5370612",
+            before_send=lambda event, hint: filter_data(coresys, event, hint),
+            auto_enabling_integrations=False,
+            default_integrations=False,
+            integrations=[
+                AioHttpIntegration(),
+                ExcepthookIntegration(),
+                DedupeIntegration(),
+                AtexitIntegration(),
+                ThreadingIntegration(),
+                LoggingIntegration(level=logging.WARNING, event_level=logging.CRITICAL),
+            ],
+            release=SUPERVISOR_VERSION,
+            max_breadcrumbs=30,
+        )
+
+
+def capture_exception(err: Exception) -> None:
+    """Capture an exception and send to sentry."""
+    if sentry_connected():
+        sentry_sdk.capture_exception(err)
+
+
+def close_sentry() -> None:
+    """Close the current sentry client.
+
+    This method is irreversible. A new client will have to be initialized to re-open connetion.
+    """
+    if sentry_connected():
+        _LOGGER.info("Closing connection to Supervisor Sentry")
+        sentry_sdk.Hub.current.client.close()
diff --git a/tests/addons/test_manager.py b/tests/addons/test_manager.py
index 26e1b43f0..9f350961b 100644
--- a/tests/addons/test_manager.py
+++ b/tests/addons/test_manager.py
@@ -1,15 +1,23 @@
 """Test addon manager."""
 
-from unittest.mock import PropertyMock, patch
+from unittest.mock import Mock, PropertyMock, patch
 
 from awesomeversion import AwesomeVersion
 import pytest
 
 from supervisor.addons.addon import Addon
 from supervisor.arch import CpuArch
+from supervisor.const import AddonBoot, AddonStartup, AddonState
 from supervisor.coresys import CoreSys
 from supervisor.docker.addon import DockerAddon
 from supervisor.docker.interface import DockerInterface
+from supervisor.exceptions import (
+    AddonConfigurationError,
+    AddonsError,
+    DockerAPIError,
+    DockerNotFound,
+)
+from supervisor.utils import check_exception_chain
 
 from tests.common import load_json_fixture
 from tests.const import TEST_ADDON_SLUG
@@ -65,3 +73,60 @@ async def test_image_added_removed_on_update(
         await install_addon_ssh.update()
         build.assert_called_once_with(AwesomeVersion("11.0.0"))
         install.assert_not_called()
+
+
+@pytest.mark.parametrize("err", [DockerAPIError, DockerNotFound])
+async def test_addon_boot_system_error(
+    coresys: CoreSys, install_addon_ssh: Addon, capture_exception: Mock, err
+):
+    """Test system errors during addon boot."""
+    install_addon_ssh.boot = AddonBoot.AUTO
+    with patch.object(Addon, "write_options"), patch.object(
+        DockerAddon, "run", side_effect=err
+    ):
+        await coresys.addons.boot(AddonStartup.APPLICATION)
+
+    assert install_addon_ssh.boot == AddonBoot.MANUAL
+    capture_exception.assert_not_called()
+
+
+async def test_addon_boot_user_error(
+    coresys: CoreSys, install_addon_ssh: Addon, capture_exception: Mock
+):
+    """Test user error during addon boot."""
+    install_addon_ssh.boot = AddonBoot.AUTO
+    with patch.object(Addon, "write_options", side_effect=AddonConfigurationError):
+        await coresys.addons.boot(AddonStartup.APPLICATION)
+
+    assert install_addon_ssh.boot == AddonBoot.MANUAL
+    capture_exception.assert_not_called()
+
+
+async def test_addon_boot_other_error(
+    coresys: CoreSys, install_addon_ssh: Addon, capture_exception: Mock
+):
+    """Test other errors captured during addon boot."""
+    install_addon_ssh.boot = AddonBoot.AUTO
+    err = OSError()
+    with patch.object(Addon, "write_options"), patch.object(
+        DockerAddon, "run", side_effect=err
+    ):
+        await coresys.addons.boot(AddonStartup.APPLICATION)
+
+    assert install_addon_ssh.boot == AddonBoot.AUTO
+    capture_exception.assert_called_once_with(err)
+
+
+async def test_addon_shutdown_error(
+    coresys: CoreSys, install_addon_ssh: Addon, capture_exception: Mock
+):
+    """Test errors captured during addon shutdown."""
+    install_addon_ssh.state = AddonState.STARTED
+    with patch.object(DockerAddon, "stop", side_effect=DockerNotFound()):
+        await coresys.addons.shutdown(AddonStartup.APPLICATION)
+
+    assert install_addon_ssh.state == AddonState.ERROR
+    capture_exception.assert_called_once()
+    assert check_exception_chain(
+        capture_exception.call_args[0][0], (AddonsError, DockerNotFound)
+    )
diff --git a/tests/api/test_supervisor.py b/tests/api/test_supervisor.py
index a26b142a0..50569a561 100644
--- a/tests/api/test_supervisor.py
+++ b/tests/api/test_supervisor.py
@@ -124,10 +124,25 @@ async def test_api_supervisor_options_diagnostics(
     await coresys.dbus.agent.connect(coresys.dbus.bus)
     dbus.clear()
 
-    response = await api_client.post("/supervisor/options", json={"diagnostics": True})
-    await asyncio.sleep(0)
+    with patch("supervisor.utils.sentry.sentry_sdk.init") as sentry_init:
+        response = await api_client.post(
+            "/supervisor/options", json={"diagnostics": True}
+        )
+        assert response.status == 200
+        sentry_init.assert_called_once()
 
-    assert response.status == 200
+    await asyncio.sleep(0)
+    assert dbus == ["/io/hass/os-io.hass.os.Diagnostics"]
+
+    dbus.clear()
+    with patch("supervisor.api.supervisor.close_sentry") as close_sentry:
+        response = await api_client.post(
+            "/supervisor/options", json={"diagnostics": False}
+        )
+        assert response.status == 200
+        close_sentry.assert_called_once()
+
+    await asyncio.sleep(0)
     assert dbus == ["/io/hass/os-io.hass.os.Diagnostics"]
 
 
diff --git a/tests/backups/test_manager.py b/tests/backups/test_manager.py
index b985a325d..74f91280f 100644
--- a/tests/backups/test_manager.py
+++ b/tests/backups/test_manager.py
@@ -1,11 +1,13 @@
 """Test BackupManager class."""
 
-from unittest.mock import AsyncMock, MagicMock, PropertyMock, patch
+from unittest.mock import AsyncMock, MagicMock, Mock, PropertyMock, patch
 
+from supervisor.addons.addon import Addon
 from supervisor.backups.const import BackupType
 from supervisor.backups.manager import BackupManager
 from supervisor.const import FOLDER_HOMEASSISTANT, FOLDER_SHARE, CoreState
 from supervisor.coresys import CoreSys
+from supervisor.exceptions import AddonsError, DockerError
 
 from tests.const import TEST_ADDON_SLUG
 
@@ -321,3 +323,34 @@ async def test_fail_invalid_partial_backup(
         type(coresys.supervisor), "version", new=PropertyMock(return_value="2022.08.3")
     ):
         assert await manager.do_restore_partial(backup_instance) is False
+
+
+async def test_backup_error(
+    coresys: CoreSys,
+    backup_mock: MagicMock,
+    install_addon_ssh: Addon,
+    capture_exception: Mock,
+):
+    """Test error captured when backup fails."""
+    coresys.core.state = CoreState.RUNNING
+    coresys.hardware.disk.get_disk_free_space = lambda x: 5000
+
+    backup_mock.return_value.store_addons.side_effect = (err := AddonsError())
+    await coresys.backups.do_backup_full()
+
+    capture_exception.assert_called_once_with(err)
+
+
+async def test_restore_error(
+    coresys: CoreSys, full_backup_mock: MagicMock, capture_exception: Mock
+):
+    """Test restoring full Backup."""
+    coresys.core.state = CoreState.RUNNING
+    coresys.hardware.disk.get_disk_free_space = lambda x: 5000
+    coresys.homeassistant.core.start = AsyncMock(return_value=None)
+
+    backup_instance = full_backup_mock.return_value
+    backup_instance.restore_dockerconfig.side_effect = (err := DockerError())
+    await coresys.backups.do_restore_full(backup_instance)
+
+    capture_exception.assert_called_once_with(err)
diff --git a/tests/conftest.py b/tests/conftest.py
index 44b7fdf99..580634fc4 100644
--- a/tests/conftest.py
+++ b/tests/conftest.py
@@ -3,7 +3,7 @@ from functools import partial
 from inspect import unwrap
 from pathlib import Path
 import re
-from unittest.mock import AsyncMock, MagicMock, PropertyMock, patch
+from unittest.mock import AsyncMock, MagicMock, Mock, PropertyMock, patch
 from uuid import uuid4
 
 from aiohttp import web
@@ -302,7 +302,7 @@ async def coresys(
 ) -> CoreSys:
     """Create a CoreSys Mock."""
     with patch("supervisor.bootstrap.initialize_system"), patch(
-        "supervisor.bootstrap.setup_diagnostics"
+        "supervisor.utils.sentry.sentry_sdk.init"
     ):
         coresys_obj = await initialize_coresys()
 
@@ -580,3 +580,12 @@ async def docker_logs(docker: DockerAPI) -> MagicMock:
         os.environ = {"SUPERVISOR_NAME": "hassio_supervisor"}
 
         yield container_mock.logs
+
+
+@pytest.fixture
+async def capture_exception() -> Mock:
+    """Mock capture exception method for testing."""
+    with patch("supervisor.utils.sentry.sentry_connected", return_value=True), patch(
+        "supervisor.utils.sentry.sentry_sdk.capture_exception"
+    ) as capture_exception:
+        yield capture_exception
diff --git a/tests/dbus/network/test_network_manager.py b/tests/dbus/network/test_network_manager.py
index d29293fed..ddae41cf8 100644
--- a/tests/dbus/network/test_network_manager.py
+++ b/tests/dbus/network/test_network_manager.py
@@ -1,7 +1,7 @@
 """Test NetworkInterface."""
 import asyncio
 import logging
-from unittest.mock import AsyncMock, PropertyMock, patch
+from unittest.mock import AsyncMock, Mock, PropertyMock, patch
 
 from dbus_fast.aio.message_bus import MessageBus
 import pytest
@@ -114,7 +114,9 @@ async def test_removed_devices_disconnect(network_manager: NetworkManager):
 
 
 async def test_handling_bad_devices(
-    network_manager: NetworkManager, caplog: pytest.LogCaptureFixture
+    network_manager: NetworkManager,
+    caplog: pytest.LogCaptureFixture,
+    capture_exception: Mock,
 ):
     """Test handling of bad and disappearing devices."""
     caplog.clear()
@@ -135,14 +137,12 @@ async def test_handling_bad_devices(
 
     # Unparseable introspections shouldn't happen, this one is logged and captured
     await network_manager.update()
-    with patch.object(
-        DBus, "_init_proxy", side_effect=(err := DBusParseError())
-    ), patch("supervisor.dbus.network.sentry_sdk.capture_exception") as capture:
+    with patch.object(DBus, "_init_proxy", side_effect=(err := DBusParseError())):
         await network_manager.update(
             {"Devices": [device := "/org/freedesktop/NetworkManager/Devices/102"]}
         )
         assert f"Error while processing {device}" in caplog.text
-        capture.assert_called_once_with(err)
+        capture_exception.assert_called_once_with(err)
 
     # We should be able to debug these situations if necessary
     caplog.set_level(logging.DEBUG, "supervisor.dbus.network")
diff --git a/tests/docker/test_addon.py b/tests/docker/test_addon.py
index d789464fb..26a4cb60d 100644
--- a/tests/docker/test_addon.py
+++ b/tests/docker/test_addon.py
@@ -1,14 +1,21 @@
 """Test docker addon setup."""
-from unittest.mock import MagicMock, PropertyMock, patch
+from ipaddress import IPv4Address
+from unittest.mock import MagicMock, Mock, PropertyMock, patch
 
+from docker.errors import NotFound
 import pytest
 
 from supervisor.addons import validate as vd
 from supervisor.addons.addon import Addon
 from supervisor.addons.model import Data
+from supervisor.addons.options import AddonOptions
 from supervisor.const import SYSTEMD_JOURNAL_PERSISTENT, SYSTEMD_JOURNAL_VOLATILE
 from supervisor.coresys import CoreSys
 from supervisor.docker.addon import DockerAddon
+from supervisor.exceptions import CoreDNSError, DockerNotFound
+from supervisor.plugins.dns import PluginDns
+from supervisor.resolution.const import ContextType, IssueType
+from supervisor.resolution.data import Issue
 
 from ..common import load_json_fixture
 
@@ -32,7 +39,7 @@ def fixture_addonsdata_user() -> dict[str, Data]:
         yield mock
 
 
-@pytest.fixture(name="os_environ", autouse=True)
+@pytest.fixture(name="os_environ")
 def fixture_os_environ():
     """Mock os.environ."""
     with patch("supervisor.config.os.environ") as mock:
@@ -52,7 +59,9 @@ def get_docker_addon(
     return docker_addon
 
 
-def test_base_volumes_included(coresys: CoreSys, addonsdata_system: dict[str, Data]):
+def test_base_volumes_included(
+    coresys: CoreSys, addonsdata_system: dict[str, Data], os_environ
+):
     """Dev and data volumes always included."""
     docker_addon = get_docker_addon(
         coresys, addonsdata_system, "basic-addon-config.json"
@@ -72,7 +81,7 @@ def test_base_volumes_included(coresys: CoreSys, addonsdata_system: dict[str, Da
 
 
 def test_addon_map_folder_defaults(
-    coresys: CoreSys, addonsdata_system: dict[str, Data]
+    coresys: CoreSys, addonsdata_system: dict[str, Data], os_environ
 ):
     """Validate defaults for mapped folders in addons."""
     docker_addon = get_docker_addon(
@@ -96,7 +105,9 @@ def test_addon_map_folder_defaults(
     assert str(docker_addon.sys_config.path_extern_share) not in volumes
 
 
-def test_journald_addon(coresys: CoreSys, addonsdata_system: dict[str, Data]):
+def test_journald_addon(
+    coresys: CoreSys, addonsdata_system: dict[str, Data], os_environ
+):
     """Validate volume for journald option."""
     docker_addon = get_docker_addon(
         coresys, addonsdata_system, "journald-addon-config.json"
@@ -115,7 +126,9 @@ def test_journald_addon(coresys: CoreSys, addonsdata_system: dict[str, Data]):
     assert volumes.get(str(SYSTEMD_JOURNAL_VOLATILE)).get("mode") == "ro"
 
 
-def test_not_journald_addon(coresys: CoreSys, addonsdata_system: dict[str, Data]):
+def test_not_journald_addon(
+    coresys: CoreSys, addonsdata_system: dict[str, Data], os_environ
+):
     """Validate journald option defaults off."""
     docker_addon = get_docker_addon(
         coresys, addonsdata_system, "basic-addon-config.json"
@@ -123,3 +136,68 @@ def test_not_journald_addon(coresys: CoreSys, addonsdata_system: dict[str, Data]
     volumes = docker_addon.volumes
 
     assert str(SYSTEMD_JOURNAL_PERSISTENT) not in volumes
+
+
+async def test_addon_run_docker_error(
+    coresys: CoreSys,
+    addonsdata_system: dict[str, Data],
+    capture_exception: Mock,
+    os_environ,
+):
+    """Test docker error when addon is run."""
+    await coresys.dbus.timedate.connect(coresys.dbus.bus)
+    coresys.docker.docker.containers.create.side_effect = NotFound("Missing")
+    docker_addon = get_docker_addon(
+        coresys, addonsdata_system, "basic-addon-config.json"
+    )
+
+    with patch.object(DockerAddon, "_stop"), patch.object(
+        AddonOptions, "validate", new=PropertyMock(return_value=lambda _: None)
+    ), pytest.raises(DockerNotFound):
+        await docker_addon.run()
+
+    assert (
+        Issue(IssueType.MISSING_IMAGE, ContextType.ADDON, reference="test_addon")
+        in coresys.resolution.issues
+    )
+    capture_exception.assert_not_called()
+
+
+async def test_addon_run_add_host_error(
+    coresys: CoreSys,
+    addonsdata_system: dict[str, Data],
+    capture_exception: Mock,
+    os_environ,
+):
+    """Test error adding host when addon is run."""
+    await coresys.dbus.timedate.connect(coresys.dbus.bus)
+    docker_addon = get_docker_addon(
+        coresys, addonsdata_system, "basic-addon-config.json"
+    )
+
+    with patch.object(DockerAddon, "_stop"), patch.object(
+        AddonOptions, "validate", new=PropertyMock(return_value=lambda _: None)
+    ), patch.object(PluginDns, "add_host", side_effect=(err := CoreDNSError())):
+        await docker_addon.run()
+
+        capture_exception.assert_called_once_with(err)
+
+
+async def test_addon_stop_delete_host_error(
+    coresys: CoreSys,
+    addonsdata_system: dict[str, Data],
+    capture_exception: Mock,
+):
+    """Test error deleting host when addon is stopped."""
+    docker_addon = get_docker_addon(
+        coresys, addonsdata_system, "basic-addon-config.json"
+    )
+
+    with patch.object(
+        DockerAddon,
+        "ip_address",
+        new=PropertyMock(return_value=IPv4Address("172.30.33.1")),
+    ), patch.object(PluginDns, "delete_host", side_effect=(err := CoreDNSError())):
+        await docker_addon.stop()
+
+        capture_exception.assert_called_once_with(err)
diff --git a/tests/docker/test_interface.py b/tests/docker/test_interface.py
index 8df0925b6..1dd95b414 100644
--- a/tests/docker/test_interface.py
+++ b/tests/docker/test_interface.py
@@ -206,3 +206,17 @@ async def test_attach_total_failure(coresys: CoreSys):
         DockerError
     ):
         await coresys.homeassistant.core.instance.attach(AwesomeVersion("2022.7.3"))
+
+
+@pytest.mark.parametrize("err", [DockerException(), RequestException()])
+async def test_image_pull_fail(
+    coresys: CoreSys, capture_exception: Mock, err: Exception
+):
+    """Test failure to pull image."""
+    coresys.docker.images.pull.side_effect = err
+    with pytest.raises(DockerError):
+        await coresys.homeassistant.core.instance.install(
+            AwesomeVersion("2022.7.3"), arch=CpuArch.AMD64
+        )
+
+    capture_exception.assert_called_once_with(err)
diff --git a/tests/homeassistant/test_core.py b/tests/homeassistant/test_core.py
index 1bf5c99a2..c2aba6bde 100644
--- a/tests/homeassistant/test_core.py
+++ b/tests/homeassistant/test_core.py
@@ -1,10 +1,20 @@
 """Test Home Assistant core."""
-from unittest.mock import PropertyMock, patch
+from unittest.mock import MagicMock, Mock, PropertyMock, patch
 
 import pytest
 
+from supervisor.const import CpuArch
 from supervisor.coresys import CoreSys
-from supervisor.exceptions import AudioUpdateError, HomeAssistantJobError
+from supervisor.docker.homeassistant import DockerHomeAssistant
+from supervisor.docker.interface import DockerInterface
+from supervisor.exceptions import (
+    AudioUpdateError,
+    CodeNotaryError,
+    DockerError,
+    HomeAssistantJobError,
+)
+from supervisor.homeassistant.core import HomeAssistantCore
+from supervisor.updater import Updater
 
 
 async def test_update_fails_if_out_of_date(coresys: CoreSys):
@@ -24,3 +34,99 @@ async def test_update_fails_if_out_of_date(coresys: CoreSys):
         HomeAssistantJobError
     ):
         await coresys.homeassistant.core.update()
+
+
+async def test_install_landingpage_docker_error(
+    coresys: CoreSys, capture_exception: Mock, caplog: pytest.LogCaptureFixture
+):
+    """Test install landing page fails due to docker error."""
+    coresys.security.force = True
+    with patch.object(
+        DockerHomeAssistant, "attach", side_effect=DockerError
+    ), patch.object(
+        Updater, "image_homeassistant", new=PropertyMock(return_value="homeassistant")
+    ), patch.object(
+        DockerInterface, "arch", new=PropertyMock(return_value=CpuArch.AMD64)
+    ), patch(
+        "supervisor.homeassistant.core.asyncio.sleep"
+    ) as sleep, patch(
+        "supervisor.security.module.cas_validate",
+        side_effect=[CodeNotaryError, None],
+    ):
+        await coresys.homeassistant.core.install_landingpage()
+        sleep.assert_awaited_once_with(30)
+
+    assert "Fails install landingpage, retry after 30sec" in caplog.text
+    capture_exception.assert_not_called()
+
+
+async def test_install_landingpage_other_error(
+    coresys: CoreSys, capture_exception: Mock, caplog: pytest.LogCaptureFixture
+):
+    """Test install landing page fails due to other error."""
+    coresys.docker.images.pull.side_effect = [(err := OSError()), MagicMock()]
+
+    with patch.object(
+        DockerHomeAssistant, "attach", side_effect=DockerError
+    ), patch.object(
+        Updater, "image_homeassistant", new=PropertyMock(return_value="homeassistant")
+    ), patch.object(
+        DockerInterface, "arch", new=PropertyMock(return_value=CpuArch.AMD64)
+    ), patch(
+        "supervisor.homeassistant.core.asyncio.sleep"
+    ) as sleep:
+        await coresys.homeassistant.core.install_landingpage()
+        sleep.assert_awaited_once_with(30)
+
+    assert "Fails install landingpage, retry after 30sec" in caplog.text
+    capture_exception.assert_called_once_with(err)
+
+
+async def test_install_docker_error(
+    coresys: CoreSys, capture_exception: Mock, caplog: pytest.LogCaptureFixture
+):
+    """Test install fails due to docker error."""
+    coresys.security.force = True
+    with patch.object(HomeAssistantCore, "_start"), patch.object(
+        DockerHomeAssistant, "cleanup"
+    ), patch.object(
+        Updater, "image_homeassistant", new=PropertyMock(return_value="homeassistant")
+    ), patch.object(
+        Updater, "version_homeassistant", new=PropertyMock(return_value="2022.7.3")
+    ), patch.object(
+        DockerInterface, "arch", new=PropertyMock(return_value=CpuArch.AMD64)
+    ), patch(
+        "supervisor.homeassistant.core.asyncio.sleep"
+    ) as sleep, patch(
+        "supervisor.security.module.cas_validate",
+        side_effect=[CodeNotaryError, None],
+    ):
+        await coresys.homeassistant.core.install()
+        sleep.assert_awaited_once_with(30)
+
+    assert "Error on Home Assistant installation. Retry in 30sec" in caplog.text
+    capture_exception.assert_not_called()
+
+
+async def test_install_other_error(
+    coresys: CoreSys, capture_exception: Mock, caplog: pytest.LogCaptureFixture
+):
+    """Test install fails due to other error."""
+    coresys.docker.images.pull.side_effect = [(err := OSError()), MagicMock()]
+
+    with patch.object(HomeAssistantCore, "_start"), patch.object(
+        DockerHomeAssistant, "cleanup"
+    ), patch.object(
+        Updater, "image_homeassistant", new=PropertyMock(return_value="homeassistant")
+    ), patch.object(
+        Updater, "version_homeassistant", new=PropertyMock(return_value="2022.7.3")
+    ), patch.object(
+        DockerInterface, "arch", new=PropertyMock(return_value=CpuArch.AMD64)
+    ), patch(
+        "supervisor.homeassistant.core.asyncio.sleep"
+    ) as sleep:
+        await coresys.homeassistant.core.install()
+        sleep.assert_awaited_once_with(30)
+
+    assert "Error on Home Assistant installation. Retry in 30sec" in caplog.text
+    capture_exception.assert_called_once_with(err)
diff --git a/tests/jobs/test_job_decorator.py b/tests/jobs/test_job_decorator.py
index 1954b7fde..c3f8ca296 100644
--- a/tests/jobs/test_job_decorator.py
+++ b/tests/jobs/test_job_decorator.py
@@ -2,7 +2,7 @@
 # pylint: disable=protected-access,import-error
 import asyncio
 from datetime import timedelta
-from unittest.mock import AsyncMock, PropertyMock, patch
+from unittest.mock import AsyncMock, Mock, PropertyMock, patch
 
 from aiohttp.client_exceptions import ClientError
 import pytest
@@ -512,3 +512,26 @@ async def test_unhealthy(coresys: CoreSys, caplog: pytest.LogCaptureFixture):
 
     coresys.jobs.ignore_conditions = [JobCondition.HEALTHY]
     assert await test.execute()
+
+
+async def test_unhandled_exception(coresys: CoreSys, capture_exception: Mock):
+    """Test an unhandled exception from job."""
+    err = OSError()
+
+    class TestClass:
+        """Test class."""
+
+        def __init__(self, coresys: CoreSys):
+            """Initialize the test class."""
+            self.coresys = coresys
+
+        @Job(conditions=[JobCondition.HEALTHY])
+        async def execute(self) -> None:
+            """Execute the class method."""
+            raise err
+
+    test = TestClass(coresys)
+    with pytest.raises(JobException):
+        await test.execute()
+
+    capture_exception.assert_called_once_with(err)
diff --git a/tests/plugins/test_plugin_base.py b/tests/plugins/test_plugin_base.py
index 802fc23a7..7a87036c6 100644
--- a/tests/plugins/test_plugin_base.py
+++ b/tests/plugins/test_plugin_base.py
@@ -1,19 +1,21 @@
 """Test base plugin functionality."""
 import asyncio
-from unittest.mock import PropertyMock, patch
+from unittest.mock import Mock, PropertyMock, patch
 
 from awesomeversion import AwesomeVersion
 import pytest
 
-from supervisor.const import BusEvent
+from supervisor.const import BusEvent, CpuArch
 from supervisor.coresys import CoreSys
 from supervisor.docker.const import ContainerState
+from supervisor.docker.interface import DockerInterface
 from supervisor.docker.monitor import DockerContainerStateEvent
 from supervisor.exceptions import (
     AudioError,
     AudioJobError,
     CliError,
     CliJobError,
+    CodeNotaryUntrusted,
     CoreDNSError,
     CoreDNSJobError,
     DockerError,
@@ -30,6 +32,7 @@ from supervisor.plugins.cli import PluginCli
 from supervisor.plugins.dns import PluginDns
 from supervisor.plugins.multicast import PluginMulticast
 from supervisor.plugins.observer import PluginObserver
+from supervisor.utils import check_exception_chain
 
 
 @pytest.fixture(name="plugin")
@@ -159,16 +162,16 @@ async def test_plugin_watchdog(coresys: CoreSys, plugin: PluginBase) -> None:
 @pytest.mark.parametrize(
     "plugin,error",
     [
-        (PluginAudio, AudioError),
-        (PluginCli, CliError),
-        (PluginDns, CoreDNSError),
-        (PluginMulticast, MulticastError),
-        (PluginObserver, ObserverError),
+        (PluginAudio, AudioError()),
+        (PluginCli, CliError()),
+        (PluginDns, CoreDNSError()),
+        (PluginMulticast, MulticastError()),
+        (PluginObserver, ObserverError()),
     ],
     indirect=["plugin"],
 )
 async def test_plugin_watchdog_rebuild_on_failure(
-    coresys: CoreSys, plugin: PluginBase, error: PluginError
+    coresys: CoreSys, capture_exception: Mock, plugin: PluginBase, error: PluginError
 ) -> None:
     """Test plugin watchdog rebuilds if start fails."""
     with patch.object(type(plugin.instance), "attach"), patch.object(
@@ -201,6 +204,8 @@ async def test_plugin_watchdog_rebuild_on_failure(
         start.assert_called_once()
         rebuild.assert_called_once()
 
+    capture_exception.assert_called_once_with(error)
+
 
 @pytest.mark.parametrize(
     "plugin",
@@ -331,3 +336,25 @@ async def test_update_fails_if_out_of_date(
         type(coresys.supervisor), "need_update", new=PropertyMock(return_value=True)
     ), pytest.raises(error):
         await plugin.update()
+
+
+@pytest.mark.parametrize(
+    "plugin",
+    [PluginAudio, PluginCli, PluginDns, PluginMulticast, PluginObserver],
+    indirect=True,
+)
+async def test_repair_failed(
+    coresys: CoreSys, capture_exception: Mock, plugin: PluginBase
+):
+    """Test repair failed."""
+    with patch.object(
+        DockerInterface, "exists", return_value=mock_is_running(False)
+    ), patch.object(
+        DockerInterface, "arch", new=PropertyMock(return_value=CpuArch.AMD64)
+    ), patch(
+        "supervisor.security.module.cas_validate", side_effect=CodeNotaryUntrusted
+    ):
+        await plugin.repair()
+
+    capture_exception.assert_called_once()
+    assert check_exception_chain(capture_exception.call_args[0][0], CodeNotaryUntrusted)
diff --git a/tests/resolution/check/test_check_dns_server_failure.py b/tests/resolution/check/test_check_dns_server_failure.py
index 9096ccf2f..68ed4f6d8 100644
--- a/tests/resolution/check/test_check_dns_server_failure.py
+++ b/tests/resolution/check/test_check_dns_server_failure.py
@@ -1,5 +1,5 @@
 """Test check DNS Servers for failures."""
-from unittest.mock import AsyncMock, call, patch
+from unittest.mock import AsyncMock, Mock, call, patch
 
 from aiodns.error import DNSError
 import pytest
@@ -27,7 +27,7 @@ async def test_base(coresys: CoreSys):
     assert dns_server.enabled
 
 
-async def test_check(coresys: CoreSys, dns_query: AsyncMock):
+async def test_check(coresys: CoreSys, dns_query: AsyncMock, capture_exception: Mock):
     """Test check for DNS server failures."""
     dns_server = CheckDNSServer(coresys)
     coresys.core.state = CoreState.RUNNING
@@ -50,7 +50,7 @@ async def test_check(coresys: CoreSys, dns_query: AsyncMock):
     coresys.plugins.dns.servers = []
     assert dns_server.dns_servers == ["dns://192.168.30.1"]
 
-    dns_query.side_effect = DNSError()
+    dns_query.side_effect = (err := DNSError())
     await dns_server.run_check.__wrapped__(dns_server)
     dns_query.assert_called_once_with("_checkdns.home-assistant.io", "A")
 
@@ -58,6 +58,7 @@ async def test_check(coresys: CoreSys, dns_query: AsyncMock):
     assert coresys.resolution.issues[0].type is IssueType.DNS_SERVER_FAILED
     assert coresys.resolution.issues[0].context is ContextType.DNS_SERVER
     assert coresys.resolution.issues[0].reference == "dns://192.168.30.1"
+    capture_exception.assert_called_once_with(err)
 
 
 async def test_approve(coresys: CoreSys, dns_query: AsyncMock):
diff --git a/tests/resolution/check/test_check_dns_server_ipv6_error.py b/tests/resolution/check/test_check_dns_server_ipv6_error.py
index ecd1e0b90..744b249d9 100644
--- a/tests/resolution/check/test_check_dns_server_ipv6_error.py
+++ b/tests/resolution/check/test_check_dns_server_ipv6_error.py
@@ -1,5 +1,5 @@
 """Test check DNS Servers for IPv6 errors."""
-from unittest.mock import AsyncMock, call, patch
+from unittest.mock import AsyncMock, Mock, call, patch
 
 from aiodns.error import DNSError
 import pytest
@@ -27,7 +27,7 @@ async def test_base(coresys: CoreSys):
     assert dns_server_ipv6.enabled
 
 
-async def test_check(coresys: CoreSys, dns_query: AsyncMock):
+async def test_check(coresys: CoreSys, dns_query: AsyncMock, capture_exception: Mock):
     """Test check for DNS server IPv6 errors."""
     dns_server_ipv6 = CheckDNSServerIPv6(coresys)
     coresys.core.state = CoreState.RUNNING
@@ -56,7 +56,7 @@ async def test_check(coresys: CoreSys, dns_query: AsyncMock):
     assert len(coresys.resolution.issues) == 0
 
     dns_query.reset_mock()
-    dns_query.side_effect = DNSError(4, "Domain name not found")
+    dns_query.side_effect = (err := DNSError(4, "Domain name not found"))
     await dns_server_ipv6.run_check.__wrapped__(dns_server_ipv6)
     dns_query.assert_called_once_with("_checkdns.home-assistant.io", "AAAA")
 
@@ -64,6 +64,7 @@ async def test_check(coresys: CoreSys, dns_query: AsyncMock):
     assert coresys.resolution.issues[0].type is IssueType.DNS_SERVER_IPV6_ERROR
     assert coresys.resolution.issues[0].context is ContextType.DNS_SERVER
     assert coresys.resolution.issues[0].reference == "dns://192.168.30.1"
+    capture_exception.assert_called_once_with(err)
 
 
 async def test_approve(coresys: CoreSys, dns_query: AsyncMock):
diff --git a/tests/resolution/test_check.py b/tests/resolution/test_check.py
new file mode 100644
index 000000000..ec2018046
--- /dev/null
+++ b/tests/resolution/test_check.py
@@ -0,0 +1,21 @@
+"""Test checks."""
+
+from unittest.mock import Mock, patch
+
+from supervisor.const import CoreState
+from supervisor.coresys import CoreSys
+from supervisor.resolution.checks.core_security import CheckCoreSecurity
+from supervisor.utils import check_exception_chain
+
+
+async def test_check_system_error(coresys: CoreSys, capture_exception: Mock):
+    """Test error while checking system."""
+    coresys.core.state = CoreState.STARTUP
+
+    with patch.object(CheckCoreSecurity, "run_check", side_effect=ValueError), patch(
+        "shutil.disk_usage", return_value=(42, 42, 2 * (1024.0**3))
+    ):
+        await coresys.resolution.check.check_system()
+
+    capture_exception.assert_called_once()
+    assert check_exception_chain(capture_exception.call_args[0][0], ValueError)
diff --git a/tests/resolution/test_evaluation.py b/tests/resolution/test_evaluation.py
new file mode 100644
index 000000000..ee2973de4
--- /dev/null
+++ b/tests/resolution/test_evaluation.py
@@ -0,0 +1,21 @@
+"""Test evaluations."""
+
+from unittest.mock import Mock, patch
+
+from supervisor.const import CoreState
+from supervisor.coresys import CoreSys
+from supervisor.utils import check_exception_chain
+
+
+async def test_evaluate_system_error(coresys: CoreSys, capture_exception: Mock):
+    """Test error while evaluating system."""
+    coresys.core.state = CoreState.RUNNING
+
+    with patch(
+        "supervisor.resolution.evaluations.source_mods.calc_checksum_path_sourcecode",
+        side_effect=OSError,
+    ):
+        await coresys.resolution.evaluate.evaluate_system()
+
+    capture_exception.assert_called_once()
+    assert check_exception_chain(capture_exception.call_args[0][0], OSError)
diff --git a/tests/test_supervisor.py b/tests/test_supervisor.py
index 14162d527..9ff4b222e 100644
--- a/tests/test_supervisor.py
+++ b/tests/test_supervisor.py
@@ -1,12 +1,17 @@
 """Test supervisor object."""
 
 from datetime import timedelta
-from unittest.mock import AsyncMock, PropertyMock, patch
+from unittest.mock import AsyncMock, Mock, PropertyMock, patch
 
 from aiohttp.client_exceptions import ClientError
+from awesomeversion import AwesomeVersion
 import pytest
 
 from supervisor.coresys import CoreSys
+from supervisor.docker.supervisor import DockerSupervisor
+from supervisor.exceptions import DockerError, SupervisorUpdateError
+from supervisor.resolution.const import ContextType, IssueType
+from supervisor.resolution.data import Issue
 from supervisor.supervisor import Supervisor
 
 
@@ -63,3 +68,18 @@ async def test_connectivity_check_throttling(
         await coresys.supervisor.check_connectivity()
 
     assert websession.head.call_count == call_count
+
+
+async def test_update_failed(coresys: CoreSys, capture_exception: Mock):
+    """Test update failure."""
+    err = DockerError()
+    with patch.object(DockerSupervisor, "install", side_effect=err), patch.object(
+        type(coresys.supervisor), "update_apparmor"
+    ), pytest.raises(SupervisorUpdateError):
+        await coresys.supervisor.update(AwesomeVersion("1.0"))
+
+    capture_exception.assert_called_once_with(err)
+    assert (
+        Issue(IssueType.UPDATE_FAILED, ContextType.SUPERVISOR)
+        in coresys.resolution.issues
+    )