diff --git a/deploy/sre-prometheus/management-cluster/100-machine-out-of-compliance.PrometheusRule.yaml b/deploy/sre-prometheus/management-cluster/100-machine-out-of-compliance.PrometheusRule.yaml
index 8f9320f1de..9356ebf3ba 100644
--- a/deploy/sre-prometheus/management-cluster/100-machine-out-of-compliance.PrometheusRule.yaml
+++ b/deploy/sre-prometheus/management-cluster/100-machine-out-of-compliance.PrometheusRule.yaml
@@ -10,15 +10,29 @@ spec:
   groups:
   - name: sre-machine-out-of-compliance
     rules:
+    # Critical alert for machines truly stuck (>35 days = clear failure)
     - alert: MachineOutOfComplianceSRE
       # https://issues.redhat.com/browse/OSD-17905
       # This alert is a fallback in case the workload in https://issues.redhat.com/browse/OSD-17902 doesn't do it's job.
-      expr: (time() - mapi_machine_created_timestamp_seconds) > 2419200
-      for: 60m
+      # Fires when ANY machine exceeds 35 days old, indicating compliance-monkey failed to replace it.
+      expr: (time() - mapi_machine_created_timestamp_seconds) > 3024000
+      for: 1h
       labels:
         severity: critical
         namespace: "{{ $labels.namespace }}"
         node: "{{ $labels.node }}"
         link: "https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md"
       annotations:
-        message:  A machine on a management cluster is older than 28 days.
+        message: A machine on a management cluster is older than 35 days, indicating a compliance-monkey failure.
+    # Warning alert for queue backlogs (multiple machines aging out simultaneously)
+    - alert: MachineOutOfComplianceSREWarning
+      # https://issues.redhat.com/browse/OSD-17905
+      # Fires when multiple machines are >28 days old, indicating compliance-monkey queue backup.
+      # This is expected when many machines age out simultaneously but warrants monitoring.
+      expr: count((time() - mapi_machine_created_timestamp_seconds) > 2419200) > 5
+      for: 4h
+      labels:
+        severity: warning
+        link: "https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md"
+      annotations:
+        message: "{{ $value }} machines on a management cluster are older than 28 days, indicating a compliance-monkey queue backup."
diff --git a/hack/00-osd-managed-cluster-config-integration.yaml.tmpl b/hack/00-osd-managed-cluster-config-integration.yaml.tmpl
index 3461e82a4b..5fad1ed146 100644
--- a/hack/00-osd-managed-cluster-config-integration.yaml.tmpl
+++ b/hack/00-osd-managed-cluster-config-integration.yaml.tmpl
@@ -49076,15 +49076,26 @@ objects:
         - name: sre-machine-out-of-compliance
           rules:
           - alert: MachineOutOfComplianceSRE
-            expr: (time() - mapi_machine_created_timestamp_seconds) > 2419200
-            for: 60m
+            expr: (time() - mapi_machine_created_timestamp_seconds) > 3024000
+            for: 1h
             labels:
               severity: critical
               namespace: '{{ $labels.namespace }}'
               node: '{{ $labels.node }}'
               link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
             annotations:
-              message: A machine on a management cluster is older than 28 days.
+              message: A machine on a management cluster is older than 35 days, indicating
+                a compliance-monkey failure.
+          - alert: MachineOutOfComplianceSREWarning
+            expr: count((time() - mapi_machine_created_timestamp_seconds) > 2419200)
+              > 5
+            for: 4h
+            labels:
+              severity: warning
+              link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
+            annotations:
+              message: '{{ $value }} machines on a management cluster are older than
+                28 days, indicating a compliance-monkey queue backup.'
     - apiVersion: monitoring.coreos.com/v1
       kind: PrometheusRule
       metadata:
diff --git a/hack/00-osd-managed-cluster-config-production.yaml.tmpl b/hack/00-osd-managed-cluster-config-production.yaml.tmpl
index 3461e82a4b..5fad1ed146 100644
--- a/hack/00-osd-managed-cluster-config-production.yaml.tmpl
+++ b/hack/00-osd-managed-cluster-config-production.yaml.tmpl
@@ -49076,15 +49076,26 @@ objects:
         - name: sre-machine-out-of-compliance
           rules:
           - alert: MachineOutOfComplianceSRE
-            expr: (time() - mapi_machine_created_timestamp_seconds) > 2419200
-            for: 60m
+            expr: (time() - mapi_machine_created_timestamp_seconds) > 3024000
+            for: 1h
             labels:
               severity: critical
               namespace: '{{ $labels.namespace }}'
               node: '{{ $labels.node }}'
               link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
             annotations:
-              message: A machine on a management cluster is older than 28 days.
+              message: A machine on a management cluster is older than 35 days, indicating
+                a compliance-monkey failure.
+          - alert: MachineOutOfComplianceSREWarning
+            expr: count((time() - mapi_machine_created_timestamp_seconds) > 2419200)
+              > 5
+            for: 4h
+            labels:
+              severity: warning
+              link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
+            annotations:
+              message: '{{ $value }} machines on a management cluster are older than
+                28 days, indicating a compliance-monkey queue backup.'
     - apiVersion: monitoring.coreos.com/v1
       kind: PrometheusRule
       metadata:
diff --git a/hack/00-osd-managed-cluster-config-stage.yaml.tmpl b/hack/00-osd-managed-cluster-config-stage.yaml.tmpl
index 3461e82a4b..5fad1ed146 100644
--- a/hack/00-osd-managed-cluster-config-stage.yaml.tmpl
+++ b/hack/00-osd-managed-cluster-config-stage.yaml.tmpl
@@ -49076,15 +49076,26 @@ objects:
         - name: sre-machine-out-of-compliance
           rules:
           - alert: MachineOutOfComplianceSRE
-            expr: (time() - mapi_machine_created_timestamp_seconds) > 2419200
-            for: 60m
+            expr: (time() - mapi_machine_created_timestamp_seconds) > 3024000
+            for: 1h
             labels:
               severity: critical
               namespace: '{{ $labels.namespace }}'
               node: '{{ $labels.node }}'
               link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
             annotations:
-              message: A machine on a management cluster is older than 28 days.
+              message: A machine on a management cluster is older than 35 days, indicating
+                a compliance-monkey failure.
+          - alert: MachineOutOfComplianceSREWarning
+            expr: count((time() - mapi_machine_created_timestamp_seconds) > 2419200)
+              > 5
+            for: 4h
+            labels:
+              severity: warning
+              link: https://github.com/openshift/ops-sop/blob/master/v4/alerts/hypershift/MachineOutOfCompliance.md
+            annotations:
+              message: '{{ $value }} machines on a management cluster are older than
+                28 days, indicating a compliance-monkey queue backup.'
     - apiVersion: monitoring.coreos.com/v1
       kind: PrometheusRule
       metadata: