diff --git a/supervisor/jobs/decorator.py b/supervisor/jobs/decorator.py
index bd62e3c71..0b34f48db 100644
--- a/supervisor/jobs/decorator.py
+++ b/supervisor/jobs/decorator.py
@@ -92,7 +92,7 @@ class Job(CoreSysAttributes):
             # Handle condition
             if self.conditions:
                 try:
-                    self._check_conditions()
+                    await self._check_conditions()
                 except JobConditionException as err:
                     error_msg = str(err)
                     if self.on_condition is None:
@@ -150,7 +150,7 @@ class Job(CoreSysAttributes):
 
         return wrapper
 
-    def _check_conditions(self):
+    async def _check_conditions(self):
         """Check conditions."""
         used_conditions = set(self.conditions) - set(self.sys_jobs.ignore_conditions)
         ignored_conditions = set(self.conditions) & set(self.sys_jobs.ignore_conditions)
@@ -238,13 +238,22 @@ class Job(CoreSysAttributes):
                 f"'{self._method.__qualname__}' blocked from execution, supervisor needs to be updated first"
             )
 
-        if JobCondition.PLUGINS_UPDATED in self.conditions and 0 < len(
-            [plugin for plugin in self.sys_plugins.all_plugins if plugin.need_update]
+        if JobCondition.PLUGINS_UPDATED in self.conditions and (
+            out_of_date := [
+                plugin for plugin in self.sys_plugins.all_plugins if plugin.need_update
+            ]
         ):
-            raise JobConditionException(
-                f"'{self._method.__qualname__}' blocked from execution, plugin(s) {', '.join([plugin.slug for plugin in self.sys_plugins.all_plugins if plugin.need_update])} need to be updated first"
+            errors = await asyncio.gather(
+                *[plugin.update() for plugin in out_of_date], return_exceptions=True
             )
 
+            if update_failures := [
+                out_of_date[i].slug for i in range(len(errors)) if errors[i] is not None
+            ]:
+                raise JobConditionException(
+                    f"'{self._method.__qualname__}' blocked from execution, was unable to update plugin(s) {', '.join(update_failures)} and all plugins must be up to date first"
+                )
+
     async def _acquire_exection_limit(self) -> None:
         """Process exection limits."""
         if self.limit not in (
diff --git a/tests/addons/test_addon.py b/tests/addons/test_addon.py
index fa1cf2849..e59881bd5 100644
--- a/tests/addons/test_addon.py
+++ b/tests/addons/test_addon.py
@@ -11,7 +11,7 @@ from supervisor.const import AddonState, BusEvent
 from supervisor.coresys import CoreSys
 from supervisor.docker.const import ContainerState
 from supervisor.docker.monitor import DockerContainerStateEvent
-from supervisor.exceptions import AddonsJobError
+from supervisor.exceptions import AddonsJobError, AudioUpdateError
 
 from ..const import TEST_ADDON_SLUG
 
@@ -287,6 +287,8 @@ async def test_install_update_fails_if_out_of_date(
 
     with patch.object(
         type(coresys.plugins.audio), "need_update", new=PropertyMock(return_value=True)
+    ), patch.object(
+        type(coresys.plugins.audio), "update", side_effect=AudioUpdateError
     ):
         with pytest.raises(AddonsJobError):
             await coresys.addons.install(TEST_ADDON_SLUG)
diff --git a/tests/homeassistant/test_core.py b/tests/homeassistant/test_core.py
index f7f600957..1bf5c99a2 100644
--- a/tests/homeassistant/test_core.py
+++ b/tests/homeassistant/test_core.py
@@ -4,7 +4,7 @@ from unittest.mock import PropertyMock, patch
 import pytest
 
 from supervisor.coresys import CoreSys
-from supervisor.exceptions import HomeAssistantJobError
+from supervisor.exceptions import AudioUpdateError, HomeAssistantJobError
 
 
 async def test_update_fails_if_out_of_date(coresys: CoreSys):
@@ -18,5 +18,9 @@ async def test_update_fails_if_out_of_date(coresys: CoreSys):
 
     with patch.object(
         type(coresys.plugins.audio), "need_update", new=PropertyMock(return_value=True)
-    ), pytest.raises(HomeAssistantJobError):
+    ), patch.object(
+        type(coresys.plugins.audio), "update", side_effect=AudioUpdateError
+    ), pytest.raises(
+        HomeAssistantJobError
+    ):
         await coresys.homeassistant.core.update()
diff --git a/tests/jobs/test_job_decorator.py b/tests/jobs/test_job_decorator.py
index 30e423dc0..a3fdfa697 100644
--- a/tests/jobs/test_job_decorator.py
+++ b/tests/jobs/test_job_decorator.py
@@ -9,7 +9,12 @@ import time_machine
 
 from supervisor.const import CoreState
 from supervisor.coresys import CoreSys
-from supervisor.exceptions import HassioError, JobException, PluginJobError
+from supervisor.exceptions import (
+    AudioUpdateError,
+    HassioError,
+    JobException,
+    PluginJobError,
+)
 from supervisor.jobs.const import JobExecutionLimit
 from supervisor.jobs.decorator import Job, JobCondition
 from supervisor.resolution.const import UnhealthyReason
@@ -448,8 +453,11 @@ async def test_plugins_updated(coresys: CoreSys):
 
     with patch.object(
         type(coresys.plugins.audio), "need_update", new=PropertyMock(return_value=True)
+    ), patch.object(
+        type(coresys.plugins.audio), "update", side_effect=[AudioUpdateError, None]
     ):
         assert not await test.execute()
+        assert await test.execute()
 
 
 async def test_auto_update(coresys: CoreSys):