diff --git a/docs/plans/cert-monitoring.md b/docs/plans/completed/cert-monitoring.md
similarity index 100%
rename from docs/plans/cert-monitoring.md
rename to docs/plans/completed/cert-monitoring.md
diff --git a/services/monitoring/blackbox.nix b/services/monitoring/blackbox.nix
new file mode 100644
index 0000000..47bd430
--- /dev/null
+++ b/services/monitoring/blackbox.nix
@@ -0,0 +1,109 @@
+{ pkgs, ... }:
+let
+  # TLS endpoints to monitor for certificate expiration
+  # These are all services using ACME certificates from OpenBao PKI
+  tlsTargets = [
+    # Direct ACME certs (security.acme.certs)
+    "https://vault.home.2rjus.net:8200"
+    "https://auth.home.2rjus.net"
+    "https://testvm01.home.2rjus.net"
+
+    # Caddy auto-TLS on http-proxy
+    "https://nzbget.home.2rjus.net"
+    "https://radarr.home.2rjus.net"
+    "https://sonarr.home.2rjus.net"
+    "https://ha.home.2rjus.net"
+    "https://z2m.home.2rjus.net"
+    "https://prometheus.home.2rjus.net"
+    "https://alertmanager.home.2rjus.net"
+    "https://grafana.home.2rjus.net"
+    "https://jelly.home.2rjus.net"
+    "https://pyroscope.home.2rjus.net"
+    "https://pushgw.home.2rjus.net"
+
+    # Caddy auto-TLS on nix-cache01
+    "https://nix-cache.home.2rjus.net"
+
+    # Caddy auto-TLS on grafana01
+    "https://grafana-test.home.2rjus.net"
+  ];
+in
+{
+  services.prometheus.exporters.blackbox = {
+    enable = true;
+    configFile = pkgs.writeText "blackbox.yml" ''
+      modules:
+        https_cert:
+          prober: http
+          timeout: 10s
+          http:
+            fail_if_not_ssl: true
+            preferred_ip_protocol: ip4
+    '';
+  };
+
+  # Add blackbox scrape config and alert rules to Prometheus
+  services.prometheus = {
+    scrapeConfigs = [
+      {
+        job_name = "blackbox_tls";
+        metrics_path = "/probe";
+        params = {
+          module = [ "https_cert" ];
+        };
+        static_configs = [{
+          targets = tlsTargets;
+        }];
+        relabel_configs = [
+          # Pass the target URL to blackbox as a parameter
+          {
+            source_labels = [ "__address__" ];
+            target_label = "__param_target";
+          }
+          # Use the target URL as the instance label
+          {
+            source_labels = [ "__param_target" ];
+            target_label = "instance";
+          }
+          # Point the actual scrape at the local blackbox exporter
+          {
+            target_label = "__address__";
+            replacement = "127.0.0.1:9115";
+          }
+        ];
+      }
+    ];
+
+    rules = [
+      ''
+        groups:
+          - name: certificate_rules
+            rules:
+              - alert: tls_certificate_expiring_soon
+                expr: (probe_ssl_earliest_cert_expiry - time()) < 86400 * 7
+                for: 1h
+                labels:
+                  severity: warning
+                annotations:
+                  summary: "TLS certificate expiring soon on {{ $labels.instance }}"
+                  description: "The TLS certificate for {{ $labels.instance }} expires in less than 7 days."
+              - alert: tls_certificate_expiring_critical
+                expr: (probe_ssl_earliest_cert_expiry - time()) < 86400
+                for: 0m
+                labels:
+                  severity: critical
+                annotations:
+                  summary: "TLS certificate expiring within 24h on {{ $labels.instance }}"
+                  description: "The TLS certificate for {{ $labels.instance }} expires in less than 24 hours. Immediate action required."
+              - alert: tls_probe_failed
+                expr: probe_success{job="blackbox_tls"} == 0
+                for: 5m
+                labels:
+                  severity: warning
+                annotations:
+                  summary: "TLS probe failed for {{ $labels.instance }}"
+                  description: "Cannot connect to {{ $labels.instance }} to check TLS certificate. The service may be down or unreachable."
+      ''
+    ];
+  };
+}
diff --git a/services/monitoring/default.nix b/services/monitoring/default.nix
index 9c96ffd..8a8b1a8 100644
--- a/services/monitoring/default.nix
+++ b/services/monitoring/default.nix
@@ -4,6 +4,7 @@
     ./loki.nix
     ./grafana.nix
     ./prometheus.nix
+    ./blackbox.nix
     ./pve.nix
     ./alerttonotify.nix
     ./pyroscope.nix