diff --git a/grafana-alerts.tf b/grafana-alerts.tf
new file mode 100644
index 0000000..5df0b66
--- /dev/null
+++ b/grafana-alerts.tf
@@ -0,0 +1,17 @@
+module "grafana_alerts" {
+  for_each = {
+    for alert in local.env_vars.grafana.alerts :
+    alert.grafana_title => alert
+  }
+  source          = "./modules/grafana_alerts"
+  local_directory = each.value.local_directory
+  folder_title    = each.value.grafana_title
+  folder_uid      = each.value.folder_uid
+  folders = [
+    {
+      title = each.value.grafana_title
+      uid   = each.value.folder_uid
+    }
+  ]
+  datasource_uids = module.grafana_data_sources.uids
+}
diff --git a/grafana/alerts/demeter/kupo-dolos.json b/grafana/alerts/demeter/kupo-dolos.json
new file mode 100644
index 0000000..052f0e3
--- /dev/null
+++ b/grafana/alerts/demeter/kupo-dolos.json
@@ -0,0 +1,137 @@
+{
+    "apiVersion": 1,
+    "groups": [
+        {
+            "orgId": 1,
+            "name": "Kupo Dolos",
+            "folder": "Demeter",
+            "interval": "1m",
+            "rules": [
+                {
+                    "uid": "bkl0kdlckpstale",
+                    "title": "Kupo (Dolos) checkpoint is stale",
+                    "condition": "C",
+                    "for": "10m",
+                    "data": [
+                        {
+                            "refId": "A",
+                            "relativeTimeRange": {
+                                "from": 900,
+                                "to": 0
+                            },
+                            "datasourceUid": "${datasource_uid_map.gke_blinklabs-demeter_us-central1_dmtr-cluster-prometheus}",
+                            "model": {
+                                "datasource": {
+                                    "type": "prometheus",
+                                    "uid": "${datasource_uid_map.gke_blinklabs-demeter_us-central1_dmtr-cluster-prometheus}"
+                                },
+                                "editorMode": "code",
+                                "expr": "changes(kupo_most_recent_checkpoint{pod=~\".*dolos.*\"}[15m]) and on (pod) (kupo_connection_status{pod=~\".*dolos.*\"} == 1)",
+                                "instant": true,
+                                "intervalMs": 1000,
+                                "legendFormat": "__auto",
+                                "maxDataPoints": 43200,
+                                "range": false,
+                                "refId": "A"
+                            }
+                        },
+                        {
+                            "refId": "B",
+                            "relativeTimeRange": {
+                                "from": 0,
+                                "to": 0
+                            },
+                            "datasourceUid": "__expr__",
+                            "model": {
+                                "conditions": [
+                                    {
+                                        "evaluator": {
+                                            "params": [
+                                                0,
+                                                0
+                                            ],
+                                            "type": "gt"
+                                        },
+                                        "operator": {
+                                            "type": "and"
+                                        },
+                                        "query": {
+                                            "params": []
+                                        },
+                                        "reducer": {
+                                            "params": [],
+                                            "type": "last"
+                                        },
+                                        "type": "query"
+                                    }
+                                ],
+                                "datasource": {
+                                    "name": "Expression",
+                                    "type": "__expr__",
+                                    "uid": "__expr__"
+                                },
+                                "expression": "A",
+                                "hide": false,
+                                "reducer": "last",
+                                "refId": "B",
+                                "type": "reduce"
+                            }
+                        },
+                        {
+                            "refId": "C",
+                            "relativeTimeRange": {
+                                "from": 0,
+                                "to": 0
+                            },
+                            "datasourceUid": "__expr__",
+                            "model": {
+                                "conditions": [
+                                    {
+                                        "evaluator": {
+                                            "params": [
+                                                1,
+                                                0
+                                            ],
+                                            "type": "lt"
+                                        },
+                                        "operator": {
+                                            "type": "and"
+                                        },
+                                        "query": {
+                                            "params": []
+                                        },
+                                        "reducer": {
+                                            "params": [],
+                                            "type": "avg"
+                                        },
+                                        "type": "query"
+                                    }
+                                ],
+                                "datasource": {
+                                    "name": "Expression",
+                                    "type": "__expr__",
+                                    "uid": "__expr__"
+                                },
+                                "expression": "B",
+                                "hide": false,
+                                "refId": "C",
+                                "type": "threshold"
+                            }
+                        }
+                    ],
+                    "noDataState": "OK",
+                    "execErrState": "KeepLast",
+                    "annotations": {
+                        "description": "A Dolos-backed Kupo instance is connected to its Dolos backend but its most recent checkpoint (kupo_most_recent_checkpoint) has not advanced for at least 15 minutes, meaning it is serving a stale index to clients. This usually indicates a wedged chain-sync session between Kupo and Dolos that a pod restart will clear.",
+                        "summary": "{{ range $k, $v := $values -}}\n{{ if (match \"C[0-9]+\" $k) -}}\nPod: {{ $v.Labels.pod }} checkpoint is not advancing\n{{ end }}\n{{ end }}"
+                    },
+                    "labels": {},
+                    "isPaused": false,
+                    "notification_settings": {
+                        "receiver": "#infra-alerts"
+                    }
+                }
+            ]
+        }
+    ]
+}
diff --git a/grafana/dashboards/shared/kupo-dolos.json b/grafana/dashboards/shared/kupo-dolos.json
index 8ff8f41..a24e407 100644
--- a/grafana/dashboards/shared/kupo-dolos.json
+++ b/grafana/dashboards/shared/kupo-dolos.json
@@ -1726,6 +1726,122 @@
       ],
       "title": "CPU Usage (cores)",
       "type": "timeseries"
+    },
+    {
+      "collapsed": false,
+      "gridPos": {
+        "h": 1,
+        "w": 24,
+        "x": 0,
+        "y": 55
+      },
+      "id": 107,
+      "panels": [],
+      "title": "Checkpoint Health",
+      "type": "row"
+    },
+    {
+      "datasource": {
+        "type": "prometheus",
+        "uid": "$datasource"
+      },
+      "description": "Number of times each Dolos-backed Kupo instance's most recent checkpoint (kupo_most_recent_checkpoint) advanced in the last 15 minutes. A healthy, syncing instance advances continuously; a value of 0 means the checkpoint is frozen (wedged chain-sync with Dolos) and the pod is serving a stale index. This is the signal behind the \"Kupo (Dolos) checkpoint is stale\" alert.",
+      "fieldConfig": {
+        "defaults": {
+          "color": {
+            "mode": "thresholds"
+          },
+          "custom": {
+            "axisBorderShow": false,
+            "axisCenteredZero": false,
+            "axisColorMode": "text",
+            "axisLabel": "checkpoint changes / 15m",
+            "axisPlacement": "auto",
+            "barAlignment": 0,
+            "barWidthFactor": 0.6,
+            "drawStyle": "line",
+            "fillOpacity": 10,
+            "gradientMode": "none",
+            "hideFrom": {
+              "legend": false,
+              "tooltip": false,
+              "viz": false
+            },
+            "insertNulls": false,
+            "lineInterpolation": "linear",
+            "lineWidth": 2,
+            "pointSize": 5,
+            "scaleDistribution": {
+              "type": "linear"
+            },
+            "showPoints": "auto",
+            "spanNulls": false,
+            "stacking": {
+              "group": "A",
+              "mode": "none"
+            },
+            "thresholdsStyle": {
+              "mode": "off"
+            }
+          },
+          "mappings": [],
+          "min": 0,
+          "thresholds": {
+            "mode": "absolute",
+            "steps": [
+              {
+                "color": "red",
+                "value": 0
+              },
+              {
+                "color": "green",
+                "value": 1
+              }
+            ]
+          },
+          "unit": "short"
+        },
+        "overrides": []
+      },
+      "gridPos": {
+        "h": 8,
+        "w": 24,
+        "x": 0,
+        "y": 56
+      },
+      "id": 20,
+      "options": {
+        "legend": {
+          "calcs": [
+            "lastNotNull",
+            "min"
+          ],
+          "displayMode": "table",
+          "placement": "bottom",
+          "showLegend": true
+        },
+        "tooltip": {
+          "hideZeros": false,
+          "mode": "multi",
+          "sort": "asc"
+        }
+      },
+      "pluginVersion": "12.4.0",
+      "targets": [
+        {
+          "datasource": {
+            "type": "prometheus",
+            "uid": "$datasource"
+          },
+          "editorMode": "code",
+          "expr": "changes(kupo_most_recent_checkpoint{pod=~\".*$network.*\"}[15m]) and on (pod) (kupo_connection_status{pod=~\".*$network.*\"} == 1)",
+          "legendFormat": "{{pod}}",
+          "range": true,
+          "refId": "A"
+        }
+      ],
+      "title": "Checkpoint Advancement (changes / 15m)",
+      "type": "timeseries"
     }
   ],
   "preload": false,
diff --git a/modules/grafana_alerts/main.tf b/modules/grafana_alerts/main.tf
index 61f5ab8..0d9e8a3 100644
--- a/modules/grafana_alerts/main.tf
+++ b/modules/grafana_alerts/main.tf
@@ -5,8 +5,8 @@ resource "grafana_folder" "this" {
 
 resource "grafana_rule_group" "this" {
   for_each = {
-    for file in fileset("${path.root}/../${var.local_directory}", "*.json") :
-    file => jsondecode(templatefile("${path.root}/../${var.local_directory}/${file}", {
+    for file in fileset("${path.root}/${var.local_directory}", "*.json") :
+    file => jsondecode(templatefile("${path.root}/${var.local_directory}/${file}", {
       datasource_uid_map = var.datasource_uids
     }))
   }