diff --git a/api/src/main/java/com/cloud/event/EventTypes.java b/api/src/main/java/com/cloud/event/EventTypes.java
index 81ed185dae5a..3ef7db9ea82d 100644
--- a/api/src/main/java/com/cloud/event/EventTypes.java
+++ b/api/src/main/java/com/cloud/event/EventTypes.java
@@ -458,6 +458,7 @@ public class EventTypes {
     public static final String EVENT_MAINTENANCE_CANCEL = "MAINT.CANCEL";
     public static final String EVENT_MAINTENANCE_CANCEL_PRIMARY_STORAGE = "MAINT.CANCEL.PS";
     public static final String EVENT_MAINTENANCE_PREPARE = "MAINT.PREPARE";
+    public static final String EVENT_MAINTENANCE_PREPARE_ERROR = "MAINT.PREPARE.ERROR";
     public static final String EVENT_MAINTENANCE_PREPARE_PRIMARY_STORAGE = "MAINT.PREPARE.PS";
 
     // Primary storage pool
@@ -1046,6 +1047,7 @@ public class EventTypes {
         entityEventDetails.put(EVENT_MAINTENANCE_CANCEL, Host.class);
         entityEventDetails.put(EVENT_MAINTENANCE_CANCEL_PRIMARY_STORAGE, Host.class);
         entityEventDetails.put(EVENT_MAINTENANCE_PREPARE, Host.class);
+        entityEventDetails.put(EVENT_MAINTENANCE_PREPARE_ERROR, Host.class);
         entityEventDetails.put(EVENT_MAINTENANCE_PREPARE_PRIMARY_STORAGE, Host.class);
 
         // Primary storage pool
diff --git a/server/src/main/java/com/cloud/resource/ResourceManagerImpl.java b/server/src/main/java/com/cloud/resource/ResourceManagerImpl.java
index a6a75fc39613..1b75b93ae7b5 100755
--- a/server/src/main/java/com/cloud/resource/ResourceManagerImpl.java
+++ b/server/src/main/java/com/cloud/resource/ResourceManagerImpl.java
@@ -1723,16 +1723,31 @@ protected boolean setHostIntoErrorInMaintenance(HostVO host, List<VMInstanceVO>
         _haMgr.cancelScheduledMigrations(host);
         configureVncAccessForKVMHostFailedMigrations(host, errorVms);
         resourceStateTransitTo(host, ResourceState.Event.UnableToMaintain, _nodeId);
+        emitMaintenanceErrorEvent(host, String.format("failed to put host %s into maintenance due to running VMs that could not be migrated or VMs in error state", host));
         return false;
     }
 
+    /**
+     * Set host into ErrorInPrepareForMaintenance state. The agent monitor calls this on every check while the errors
+     * persist, so the error event is only emitted when the host enters this state.
+     */
     protected boolean setHostIntoErrorInPrepareForMaintenance(HostVO host, List<VMInstanceVO> errorVms) throws NoTransitionException {
         logger.debug("Host {} entering in PrepareForMaintenanceWithErrors state", host);
+        final boolean alreadyInErrorState = host.getResourceState() == ResourceState.ErrorInPrepareForMaintenance;
         configureVncAccessForKVMHostFailedMigrations(host, errorVms);
         resourceStateTransitTo(host, ResourceState.Event.UnableToMigrate, _nodeId);
+        if (!alreadyInErrorState) {
+            emitMaintenanceErrorEvent(host, String.format("failed to prepare host %s for maintenance due to migration or VM state errors", host));
+        }
         return false;
     }
 
+    private void emitMaintenanceErrorEvent(HostVO host, String description) {
+        final CallContext context = CallContext.current();
+        ActionEventUtils.onCompletedActionEvent(context.getCallingUserId(), context.getCallingAccountId(),
+                EventVO.LEVEL_ERROR, EventTypes.EVENT_MAINTENANCE_PREPARE_ERROR, description, host.getId(), null, 0);
+    }
+
     protected boolean setHostIntoPrepareForMaintenanceAfterErrorsFixed(HostVO host) throws NoTransitionException {
         logger.debug("Host {} entering in PrepareForMaintenance state as any previous corrections have been fixed", host);
         resourceStateTransitTo(host, ResourceState.Event.ErrorsCorrected, _nodeId);
diff --git a/server/src/test/java/com/cloud/resource/ResourceManagerImplTest.java b/server/src/test/java/com/cloud/resource/ResourceManagerImplTest.java
index a28d3aaeac07..43e8eb1db351 100644
--- a/server/src/test/java/com/cloud/resource/ResourceManagerImplTest.java
+++ b/server/src/test/java/com/cloud/resource/ResourceManagerImplTest.java
@@ -23,6 +23,8 @@
 import com.cloud.agent.api.GetVncPortCommand;
 import com.cloud.capacity.dao.CapacityDao;
 import com.cloud.event.ActionEventUtils;
+import com.cloud.event.EventTypes;
+import com.cloud.event.EventVO;
 import com.cloud.exception.InvalidParameterValueException;
 import com.cloud.ha.HighAvailabilityManager;
 import com.cloud.host.Host;
@@ -79,6 +81,7 @@
 import static org.mockito.ArgumentMatchers.anyLong;
 import static org.mockito.ArgumentMatchers.anyString;
 import static org.mockito.ArgumentMatchers.eq;
+import static org.mockito.ArgumentMatchers.isNull;
 import static org.mockito.Mockito.never;
 import static org.mockito.Mockito.times;
 import static org.mockito.Mockito.verify;
@@ -521,6 +524,7 @@ private void setupErrorVms() {
     }
 
     private void verifyErrorInMaintenanceCalls() throws NoTransitionException {
+        when(host.getResourceState()).thenReturn(ResourceState.PrepareForMaintenance);
         boolean enterMaintenanceMode = resourceManager.checkAndMaintain(hostId);
         verify(resourceManager).attemptMaintain(host);
         verify(resourceManager).setHostIntoErrorInMaintenance(eq(host), any());
@@ -528,10 +532,14 @@ private void verifyErrorInMaintenanceCalls() throws NoTransitionException {
         verify(resourceManager, never()).setHostIntoErrorInPrepareForMaintenance(any(), any());
         verify(resourceManager, never()).setHostIntoPrepareForMaintenanceAfterErrorsFixed(any());
         verify(resourceManager).resourceStateTransitTo(eq(host), eq(UnableToMaintain), anyLong());
+        actionEventUtilsMocked.verify(() -> ActionEventUtils.onCompletedActionEvent(
+                anyLong(), anyLong(), eq(EventVO.LEVEL_ERROR), eq(EventTypes.EVENT_MAINTENANCE_PREPARE_ERROR),
+                anyString(), eq(hostId), isNull(), eq(0L)));
         Assert.assertFalse(enterMaintenanceMode);
     }
 
     private void verifyErrorInPrepareForMaintenanceCalls() throws NoTransitionException {
+        when(host.getResourceState()).thenReturn(ResourceState.PrepareForMaintenance);
         boolean enterMaintenanceMode = resourceManager.checkAndMaintain(hostId);
         verify(resourceManager).attemptMaintain(host);
         verify(resourceManager).setHostIntoErrorInPrepareForMaintenance(eq(host), any());
@@ -539,9 +547,32 @@ private void verifyErrorInPrepareForMaintenanceCalls() throws NoTransitionExcept
         verify(resourceManager, never()).setHostIntoErrorInMaintenance(any(), any());
         verify(resourceManager, never()).setHostIntoPrepareForMaintenanceAfterErrorsFixed(any());
         verify(resourceManager).resourceStateTransitTo(eq(host), eq(UnableToMigrate), anyLong());
+        String expectedDescription = String.format("failed to prepare host %s for maintenance due to migration or VM state errors", host);
+        actionEventUtilsMocked.verify(() -> ActionEventUtils.onCompletedActionEvent(
+                anyLong(), anyLong(), eq(EventVO.LEVEL_ERROR), eq(EventTypes.EVENT_MAINTENANCE_PREPARE_ERROR),
+                eq(expectedDescription), eq(hostId), isNull(), eq(0L)));
         Assert.assertFalse(enterMaintenanceMode);
     }
 
+    @Test
+    public void testCheckAndMaintainStillInErrorInPrepareForMaintenanceDoesNotRepeatErrorEvent() throws NoTransitionException {
+        setupFailedMigrations();
+        setupPendingMigrationRetries();
+        when(host.getResourceState()).thenReturn(ResourceState.ErrorInPrepareForMaintenance);
+        boolean enterMaintenanceMode = resourceManager.checkAndMaintain(hostId);
+        verify(resourceManager).setHostIntoErrorInPrepareForMaintenance(eq(host), any());
+        verify(resourceManager).resourceStateTransitTo(eq(host), eq(UnableToMigrate), anyLong());
+        actionEventUtilsMocked.verify(() -> ActionEventUtils.onCompletedActionEvent(
+                anyLong(), anyLong(), anyString(), eq(EventTypes.EVENT_MAINTENANCE_PREPARE_ERROR),
+                anyString(), anyLong(), any(), anyLong()), never());
+        Assert.assertFalse(enterMaintenanceMode);
+    }
+
+    @Test
+    public void testMaintenancePrepareErrorEventMapsToHostEntity() {
+        Assert.assertEquals(Host.class, EventTypes.getEntityClassForEvent(EventTypes.EVENT_MAINTENANCE_PREPARE_ERROR));
+    }
+
     private void verifyReturnToPrepareForMaintenanceCalls() throws NoTransitionException {
         boolean enterMaintenanceMode = resourceManager.checkAndMaintain(hostId);
         verify(resourceManager).attemptMaintain(host);