diff --git a/dashcaddy-api/pylon/start-pylon.vbs b/dashcaddy-api/pylon/start-pylon.vbs
new file mode 100644
index 0000000..26d096b
--- /dev/null
+++ b/dashcaddy-api/pylon/start-pylon.vbs
@@ -0,0 +1,2 @@
+Set WshShell = CreateObject("WScript.Shell")
+WshShell.Run """C:\Program Files\nodejs\node.exe"" ""E:\CaddyCerts\sites\dashcaddy-api\pylon\dashcaddy-pylon.js""", 0, False
diff --git a/dashcaddy-api/routes/services.js b/dashcaddy-api/routes/services.js
index 06fcac8..fcb9569 100644
--- a/dashcaddy-api/routes/services.js
+++ b/dashcaddy-api/routes/services.js
@@ -65,6 +65,25 @@ module.exports = function(ctx) {
     });
   }
 
+  async function probeViaPylon(targetUrl) {
+    const pylonConfig = ctx.siteConfig?.pylon;
+    if (!pylonConfig?.url) return null;
+    try {
+      const probeUrl = `${pylonConfig.url}/probe?url=${encodeURIComponent(targetUrl)}`;
+      const headers = {};
+      if (pylonConfig.key) headers['x-pylon-key'] = pylonConfig.key;
+      const controller = new AbortController();
+      const timeout = setTimeout(() => controller.abort(), 12000);
+      const response = await ctx.fetchT(probeUrl, { method: 'GET', signal: controller.signal, headers });
+      clearTimeout(timeout);
+      if (!response.ok) return null;
+      const data = await response.json();
+      return data;
+    } catch (_) {
+      return null;
+    }
+  }
+
   async function probeServiceStatus(id, service) {
     const startedAt = process.hrtime.bigint();
     let url = resolveProbeUrl(id, service);
@@ -92,6 +111,22 @@ module.exports = function(ctx) {
       }
     }
 
+    // Pylon relay fallback — if direct probes failed, try through the pylon
+    if (error && ctx.siteConfig?.pylon) {
+      const pylonResult = await probeViaPylon(url);
+      if (pylonResult && pylonResult.status) {
+        const responseTime = Number((process.hrtime.bigint() - startedAt) / 1000000n);
+        return {
+          id,
+          isUp: pylonResult.status === 'healthy',
+          statusCode: pylonResult.statusCode || 0,
+          responseTime,
+          url,
+          via: 'pylon'
+        };
+      }
+    }
+
     const responseTime = Number((process.hrtime.bigint() - startedAt) / 1000000n);
     if (error) {
       return {