diff --git a/kubernetes/namespaces/monitoring/alerts/alerts.d/prometheus.yaml b/kubernetes/namespaces/monitoring/alerts/alerts.d/prometheus.yaml
index 25e555db..6442b13d 100644
--- a/kubernetes/namespaces/monitoring/alerts/alerts.d/prometheus.yaml
+++ b/kubernetes/namespaces/monitoring/alerts/alerts.d/prometheus.yaml
@@ -11,3 +11,12 @@ groups:
     annotations:
       summary: "Instance {{ $labels.instance }} down"
       description: "{{ $labels.instance }} of job {{ $labels.job }} has been down for more than 5 minutes."
+
+  - alert: PrometheusConfigFailed
+    expr: prometheus_config_last_reload_successful == 0
+    for: 0m
+    labels:
+      severity: page
+    annotations:
+      summary: "Prometheus config reload in pod {{ $labels.kubernetes_pod_name }} has failed"
+      description: "Prometheus instance {{ $labels.kubernetes_pod_name }} (`{{ $labels.instance }}`) has failed to reload its config."
diff --git a/kubernetes/namespaces/monitoring/prometheus/deployment.yaml b/kubernetes/namespaces/monitoring/prometheus/deployment.yaml
index 2dd1e2dc..e13f92fe 100644
--- a/kubernetes/namespaces/monitoring/prometheus/deployment.yaml
+++ b/kubernetes/namespaces/monitoring/prometheus/deployment.yaml
@@ -13,6 +13,9 @@ spec:
     metadata:
       labels:
         app: prometheus
+      annotations:
+        prometheus.io/scrape: "true"
+        prometheus.io/port: prometheus
     spec:
       serviceAccountName: prometheus
       containers:
@@ -41,6 +44,32 @@ spec:
           mountPath: /etc/prometheus
         - name: prometheus-alerts
           mountPath: /opt/pydis/prometheus/alerts.d
+      - image: ghcr.io/owl-corp/inotify-base:latest
+        imagePullPolicy: Always
+        name: prometheus-reloader
+        securityContext:
+          readOnlyRootFilesystem: true
+        volumeMounts:
+        - name: prometheus-config
+          mountPath: /opt/monitor/prom-config
+        - name: prometheus-alerts
+          mountPath: /opt/monitor/prom-alerts
+        - name: reloader-hook
+          mountPath: /opt/pydis
+        - name: reloader-tmpfs
+          mountPath: /tmp
+        env:
+          - name: INOTIFY_HOOK_SCRIPT
+            value: /opt/pydis/hook.sh
+          # When a ConfigMap volume updates we see a delete event for the old
+          # container timestamp
+          - name: INOTIFY_WATCH_EVENTS
+            value: delete
+          - name: INOTIFY_HOOK_DELAY
+            value: "5"
+        envFrom:
+        - secretRef:
+            name: prometheus-reloader-env
       restartPolicy: Always
       securityContext:
         fsGroup: 2000
@@ -56,3 +85,11 @@ spec:
         - name: prometheus-alerts
           configMap:
             name: prometheus-alert-rules
+        - name: reloader-hook
+          configMap:
+            name: prometheus-reloader-script
+            defaultMode: 0777
+        - name: reloader-tmpfs
+          emptyDir:
+            medium: Memory
+            sizeLimit: 50Mi
diff --git a/kubernetes/namespaces/monitoring/prometheus/reloader-script.yaml b/kubernetes/namespaces/monitoring/prometheus/reloader-script.yaml
new file mode 100644
index 00000000..6aae9b30
--- /dev/null
+++ b/kubernetes/namespaces/monitoring/prometheus/reloader-script.yaml
@@ -0,0 +1,38 @@
+apiVersion: v1
+kind: ConfigMap
+metadata:
+  name: prometheus-reloader-script
+  namespace: monitoring
+data:
+  hook.sh: |-
+    #!/bin/sh
+
+    set -exo pipefail
+
+    # Endpoint to call to reload Prometheus
+    RELOAD_URL="http://localhost:9090/-/reload"
+    # Icon for the webhook
+    PROMETHEUS_ICON_URL="https://static-00.iconduck.com/assets.00/prometheus-icon-511x512-1vmxbcxr.png"
+
+    echo "Detected change in mounted configmaps, reloading Prometheus..."
+
+    # Make a temporary store to keep any errors
+    RESPONSE_STORE="$(mktemp)"
+
+    # Attempt the reload, writing the response to the tempfile and the reload HTTP
+    # code to the variable
+    RELOAD_RESULT="$(curl -o "$RESPONSE_STORE" -X POST $RELOAD_URL -s -w "%{http_code}")"
+
+    # Parse and filter the response body into a JSON string
+    RESPONSE_CONTENT="$(cat "$RESPONSE_STORE")"
+    FILTERED_BODY="$(echo "$RESPONSE_CONTENT" | jq -Rsa)"
+
+    # Send a notification based on pass/failure
+    if [ $RELOAD_RESULT -eq 200 ]; then
+      BODY='{"username": "Prometheus Reloader", "embeds": [{ "title": "Prometheus Config Reload Succeeded", "description": "No errors.", "color": 6663286 } ], "avatar_url": "'"$PROMETHEUS_ICON_URL"'" }'
+    else
+      BODY='{"username": "Prometheus Reloader", "embeds": [{ "title": "Prometheus Config Reload Failed", "description": '"$FILTERED_BODY"', "color": 12799052 } ], "avatar_url": "'"$PROMETHEUS_ICON_URL"'" }'
+    fi;
+
+    # Send the webhook
+    curl -X POST -H "Content-Type: application/json" "$RELOADER_DISCORD_HOOK" -d "$BODY"
diff --git a/kubernetes/namespaces/monitoring/prometheus/secrets.yaml b/kubernetes/namespaces/monitoring/prometheus/secrets.yaml
new file mode 100644
index 00000000..875ab138
Binary files /dev/null and b/kubernetes/namespaces/monitoring/prometheus/secrets.yaml differ