diff --git a/supervisor/addons/addon.py b/supervisor/addons/addon.py
index 0d4e96620..db6c26680 100644
--- a/supervisor/addons/addon.py
+++ b/supervisor/addons/addon.py
@@ -15,6 +15,7 @@ from tempfile import TemporaryDirectory
 from typing import Any, Final
 
 import aiohttp
+from awesomeversion import AwesomeVersionCompareException
 from deepmerge import Merger
 from securetar import atomic_contents_add, secure_path
 import voluptuous as vol
@@ -279,6 +280,28 @@ class Addon(AddonModel):
         """Set auto update."""
         self.persist[ATTR_AUTO_UPDATE] = value
 
+    @property
+    def auto_update_available(self) -> bool:
+        """Return if it is safe to auto update addon."""
+        if not self.need_update or not self.auto_update:
+            return False
+
+        for version in self.breaking_versions:
+            try:
+                # Must update to latest so if true update crosses a breaking version
+                if self.version < version:
+                    return False
+            except AwesomeVersionCompareException:
+                # If version scheme changed, we may get compare exception
+                # If latest version >= breaking version then assume update will
+                # cross it as the version scheme changes
+                # If both versions have compare exception, ignore as its in the past
+                with suppress(AwesomeVersionCompareException):
+                    if self.latest_version >= version:
+                        return False
+
+        return True
+
     @property
     def watchdog(self) -> bool:
         """Return True if watchdog is enable."""
diff --git a/supervisor/addons/const.py b/supervisor/addons/const.py
index edc4d415d..f81488c42 100644
--- a/supervisor/addons/const.py
+++ b/supervisor/addons/const.py
@@ -28,6 +28,7 @@ class MappingType(StrEnum):
 
 
 ATTR_BACKUP = "backup"
+ATTR_BREAKING_VERSIONS = "breaking_versions"
 ATTR_CODENOTARY = "codenotary"
 ATTR_READ_ONLY = "read_only"
 ATTR_PATH = "path"
diff --git a/supervisor/addons/model.py b/supervisor/addons/model.py
index bc3f161c7..b1c4f657d 100644
--- a/supervisor/addons/model.py
+++ b/supervisor/addons/model.py
@@ -90,6 +90,7 @@ from ..utils import version_is_new_enough
 from .configuration import FolderMapping
 from .const import (
     ATTR_BACKUP,
+    ATTR_BREAKING_VERSIONS,
     ATTR_CODENOTARY,
     ATTR_PATH,
     ATTR_READ_ONLY,
@@ -620,6 +621,11 @@ class AddonModel(JobGroup, ABC):
         """Return Signer email address for CAS."""
         return self.data.get(ATTR_CODENOTARY)
 
+    @property
+    def breaking_versions(self) -> list[AwesomeVersion]:
+        """Return breaking versions of addon."""
+        return self.data[ATTR_BREAKING_VERSIONS]
+
     def validate_availability(self) -> None:
         """Validate if addon is available for current system."""
         return self._validate_availability(self.data, logger=_LOGGER.error)
diff --git a/supervisor/addons/validate.py b/supervisor/addons/validate.py
index 69faeba43..115896456 100644
--- a/supervisor/addons/validate.py
+++ b/supervisor/addons/validate.py
@@ -112,6 +112,7 @@ from ..validate import (
 )
 from .const import (
     ATTR_BACKUP,
+    ATTR_BREAKING_VERSIONS,
     ATTR_CODENOTARY,
     ATTR_PATH,
     ATTR_READ_ONLY,
@@ -422,6 +423,7 @@ _SCHEMA_ADDON_CONFIG = vol.Schema(
             vol.Coerce(int), vol.Range(min=10, max=300)
         ),
         vol.Optional(ATTR_JOURNALD, default=False): vol.Boolean(),
+        vol.Optional(ATTR_BREAKING_VERSIONS, default=list): [version_tag],
     },
     extra=vol.REMOVE_EXTRA,
 )
diff --git a/supervisor/misc/tasks.py b/supervisor/misc/tasks.py
index 50497c580..55333d966 100644
--- a/supervisor/misc/tasks.py
+++ b/supervisor/misc/tasks.py
@@ -95,6 +95,14 @@ class Tasks(CoreSysAttributes):
             # Evaluate available updates
             if not addon.need_update:
                 continue
+            if not addon.auto_update_available:
+                _LOGGER.debug(
+                    "Not updating add-on %s from %s to %s as that would cross a known breaking version",
+                    addon.slug,
+                    addon.version,
+                    addon.latest_version,
+                )
+                continue
             if not addon.test_update_schema():
                 _LOGGER.warning(
                     "Add-on %s will be ignored, schema tests failed", addon.slug
diff --git a/tests/addons/test_addon.py b/tests/addons/test_addon.py
index d205c890c..d69af1c4e 100644
--- a/tests/addons/test_addon.py
+++ b/tests/addons/test_addon.py
@@ -6,6 +6,7 @@ import errno
 from pathlib import Path
 from unittest.mock import MagicMock, PropertyMock, patch
 
+from awesomeversion import AwesomeVersion
 from docker.errors import DockerException, NotFound
 import pytest
 from securetar import SecureTarFile
@@ -721,3 +722,29 @@ def test_addon_pulse_error(
 
         assert "can't write pulse/client.config" in caplog.text
         assert coresys.core.healthy is False
+
+
+def test_auto_update_available(coresys: CoreSys, install_addon_example: Addon):
+    """Test auto update availability based on versions."""
+    assert install_addon_example.auto_update is False
+    assert install_addon_example.need_update is False
+    assert install_addon_example.auto_update_available is False
+
+    with patch.object(
+        Addon, "version", new=PropertyMock(return_value=AwesomeVersion("1.0"))
+    ):
+        assert install_addon_example.need_update is True
+        assert install_addon_example.auto_update_available is False
+
+        install_addon_example.auto_update = True
+        assert install_addon_example.auto_update_available is True
+
+    with patch.object(
+        Addon, "version", new=PropertyMock(return_value=AwesomeVersion("0.9"))
+    ):
+        assert install_addon_example.auto_update_available is False
+
+    with patch.object(
+        Addon, "version", new=PropertyMock(return_value=AwesomeVersion("test"))
+    ):
+        assert install_addon_example.auto_update_available is False
diff --git a/tests/fixtures/addons/local/example/config.yaml b/tests/fixtures/addons/local/example/config.yaml
index 0606593e5..8a269b562 100644
--- a/tests/fixtures/addons/local/example/config.yaml
+++ b/tests/fixtures/addons/local/example/config.yaml
@@ -20,3 +20,6 @@ schema:
   message: "str?"
 ingress: true
 ingress_port: 0
+breaking_versions:
+  - test
+  - 1.0