diff --git a/dashcaddy-api/pylon/dashcaddy-pylon.js b/dashcaddy-api/pylon/dashcaddy-pylon.js
new file mode 100644
index 0000000..d8539ae
--- /dev/null
+++ b/dashcaddy-api/pylon/dashcaddy-pylon.js
@@ -0,0 +1,232 @@
+#!/usr/bin/env node
+/**
+ * DashCaddy Pylon — Lightweight Health Relay Agent
+ *
+ * Runs on a remote network to relay health checks for services
+ * that the main DashCaddy instance can't reach directly.
+ *
+ * Zero dependencies — uses only Node.js built-ins.
+ *
+ * Usage:
+ *   node dashcaddy-pylon.js                    # port 3002, no auth
+ *   PYLON_PORT=3002 PYLON_KEY=secret node dashcaddy-pylon.js
+ *
+ * Endpoints:
+ *   GET /probe?url=<url>         Health check a URL (returns status)
+ *   GET /health                  Pylon's own health
+ *   GET /info                    Pylon metadata
+ */
+
+const http = require('http');
+const https = require('https');
+const { URL } = require('url');
+const os = require('os');
+
+const PORT = parseInt(process.env.PYLON_PORT || '3002', 10);
+const API_KEY = process.env.PYLON_KEY || '';
+const PROBE_TIMEOUT = parseInt(process.env.PYLON_TIMEOUT || '8000', 10);
+const PYLON_NAME = process.env.PYLON_NAME || os.hostname();
+
+function json(res, status, data) {
+  res.writeHead(status, { 'Content-Type': 'application/json' });
+  res.end(JSON.stringify(data));
+}
+
+function probe(targetUrl) {
+  return new Promise((resolve) => {
+    let parsed;
+    try {
+      parsed = new URL(targetUrl);
+    } catch (e) {
+      return resolve({ status: 'error', reason: 'Invalid URL', url: targetUrl });
+    }
+
+    const mod = parsed.protocol === 'https:' ? https : http;
+    const start = Date.now();
+
+    const req = mod.request({
+      hostname: parsed.hostname,
+      port: parsed.port || (parsed.protocol === 'https:' ? 443 : 80),
+      path: parsed.pathname + parsed.search,
+      method: 'HEAD',
+      timeout: PROBE_TIMEOUT,
+      rejectUnauthorized: false,
+    }, (res) => {
+      // Consume the response so the socket is freed
+      res.resume();
+      const ms = Date.now() - start;
+
+      // HEAD returned 501/405 — retry with GET
+      if (res.statusCode === 501 || res.statusCode === 405) {
+        const getReq = mod.request({
+          hostname: parsed.hostname,
+          port: parsed.port || (parsed.protocol === 'https:' ? 443 : 80),
+          path: parsed.pathname + parsed.search,
+          method: 'GET',
+          timeout: PROBE_TIMEOUT,
+          rejectUnauthorized: false,
+        }, (getRes) => {
+          getRes.resume();
+          resolve({
+            status: getRes.statusCode < 500 ? 'healthy' : 'unhealthy',
+            statusCode: getRes.statusCode,
+            responseTime: Date.now() - start,
+            url: targetUrl,
+            checkedAt: new Date().toISOString(),
+          });
+        });
+        getReq.on('error', (e) => resolve({ status: 'unhealthy', reason: e.message, responseTime: Date.now() - start, url: targetUrl, checkedAt: new Date().toISOString() }));
+        getReq.on('timeout', () => { getReq.destroy(); resolve({ status: 'unhealthy', reason: 'Timeout', responseTime: Date.now() - start, url: targetUrl, checkedAt: new Date().toISOString() }); });
+        getReq.end();
+        return;
+      }
+
+      const healthy = res.statusCode < 500;
+      resolve({
+        status: healthy ? 'healthy' : 'unhealthy',
+        statusCode: res.statusCode,
+        responseTime: ms,
+        url: targetUrl,
+        checkedAt: new Date().toISOString(),
+      });
+    });
+
+    req.on('error', (err) => {
+      // HEAD not supported — retry with GET
+      if (err.code === 'ERR_HTTP_INVALID_STATUS_CODE' || err.message?.includes('HEAD')) {
+        const getReq = mod.request({
+          hostname: parsed.hostname,
+          port: parsed.port || (parsed.protocol === 'https:' ? 443 : 80),
+          path: parsed.pathname + parsed.search,
+          method: 'GET',
+          timeout: PROBE_TIMEOUT,
+          rejectUnauthorized: false,
+        }, (getRes) => {
+          getRes.resume();
+          const ms = Date.now() - start;
+          resolve({
+            status: getRes.statusCode < 500 ? 'healthy' : 'unhealthy',
+            statusCode: getRes.statusCode,
+            responseTime: ms,
+            url: targetUrl,
+            checkedAt: new Date().toISOString(),
+          });
+        });
+        getReq.on('error', (getErr) => {
+          resolve({
+            status: 'unhealthy',
+            reason: getErr.message,
+            responseTime: Date.now() - start,
+            url: targetUrl,
+            checkedAt: new Date().toISOString(),
+          });
+        });
+        getReq.on('timeout', () => {
+          getReq.destroy();
+          resolve({
+            status: 'unhealthy',
+            reason: 'Timeout',
+            responseTime: Date.now() - start,
+            url: targetUrl,
+            checkedAt: new Date().toISOString(),
+          });
+        });
+        getReq.end();
+        return;
+      }
+
+      resolve({
+        status: 'unhealthy',
+        reason: err.message,
+        responseTime: Date.now() - start,
+        url: targetUrl,
+        checkedAt: new Date().toISOString(),
+      });
+    });
+
+    req.on('timeout', () => {
+      req.destroy();
+      resolve({
+        status: 'unhealthy',
+        reason: 'Timeout',
+        responseTime: Date.now() - start,
+        url: targetUrl,
+        checkedAt: new Date().toISOString(),
+      });
+    });
+
+    req.end();
+  });
+}
+
+const server = http.createServer(async (req, res) => {
+  const url = new URL(req.url, `http://localhost:${PORT}`);
+
+  // API key check
+  if (API_KEY) {
+    const provided = url.searchParams.get('key') || req.headers['x-pylon-key'];
+    if (provided !== API_KEY) {
+      return json(res, 401, { error: 'Invalid API key' });
+    }
+  }
+
+  // Routes
+  if (url.pathname === '/health') {
+    return json(res, 200, { status: 'ok', pylon: PYLON_NAME, uptime: process.uptime() });
+  }
+
+  if (url.pathname === '/info') {
+    return json(res, 200, {
+      pylon: PYLON_NAME,
+      hostname: os.hostname(),
+      platform: os.platform(),
+      uptime: process.uptime(),
+      version: '1.0.0',
+    });
+  }
+
+  if (url.pathname === '/probe') {
+    const targetUrl = url.searchParams.get('url');
+    if (!targetUrl) {
+      return json(res, 400, { error: 'Missing ?url= parameter' });
+    }
+
+    // Block obviously dangerous URLs (localhost probing from the pylon itself)
+    const parsed = new URL(targetUrl);
+    if (parsed.hostname === 'localhost' && parsed.port === String(PORT)) {
+      return json(res, 400, { error: 'Cannot probe self' });
+    }
+
+    const result = await probe(targetUrl);
+    return json(res, 200, result);
+  }
+
+  // Batch probe: POST /probe with JSON body { urls: [...] }
+  if (url.pathname === '/probe' && req.method === 'POST') {
+    let body = '';
+    req.on('data', c => body += c);
+    req.on('end', async () => {
+      try {
+        const { urls } = JSON.parse(body);
+        if (!Array.isArray(urls) || urls.length === 0) {
+          return json(res, 400, { error: 'Missing urls array' });
+        }
+        if (urls.length > 50) {
+          return json(res, 400, { error: 'Max 50 URLs per batch' });
+        }
+        const results = await Promise.all(urls.map(u => probe(u)));
+        return json(res, 200, { results });
+      } catch (e) {
+        return json(res, 400, { error: 'Invalid JSON body' });
+      }
+    });
+    return;
+  }
+
+  json(res, 404, { error: 'Not found' });
+});
+
+server.listen(PORT, '0.0.0.0', () => {
+  console.log(`[Pylon] ${PYLON_NAME} listening on port ${PORT}`);
+  if (API_KEY) console.log('[Pylon] API key authentication enabled');
+});
diff --git a/dashcaddy-api/pylon/dashcaddy-pylon.service b/dashcaddy-api/pylon/dashcaddy-pylon.service
new file mode 100644
index 0000000..c7b2493
--- /dev/null
+++ b/dashcaddy-api/pylon/dashcaddy-pylon.service
@@ -0,0 +1,19 @@
+[Unit]
+Description=DashCaddy Pylon — Health Check Relay
+After=network.target
+
+[Service]
+Type=simple
+ExecStart=/usr/bin/node /opt/dashcaddy-pylon/dashcaddy-pylon.js
+Restart=always
+RestartSec=5
+Environment=PYLON_PORT=3002
+Environment=PYLON_NAME=%H
+# Uncomment and set a shared key for authentication:
+#Environment=PYLON_KEY=your-shared-secret
+StandardOutput=journal
+StandardError=journal
+SyslogIdentifier=dashcaddy-pylon
+
+[Install]
+WantedBy=multi-user.target
diff --git a/dashcaddy-api/routes/health.js b/dashcaddy-api/routes/health.js
index ac1cbe5..9f34fe2 100644
--- a/dashcaddy-api/routes/health.js
+++ b/dashcaddy-api/routes/health.js
@@ -15,6 +15,70 @@ module.exports = function(ctx) {
   let serviceHealthCache = {};
   let lastHealthCheck = null;
 
+  /**
+   * Check a URL directly via fetch. Returns health object or null on failure.
+   */
+  async function checkDirect(url) {
+    // Try HEAD first
+    try {
+      const controller = new AbortController();
+      const timeout = setTimeout(() => controller.abort(), 5000);
+      const response = await ctx.fetchT(url, { method: 'HEAD', signal: controller.signal, redirect: 'follow' });
+      clearTimeout(timeout);
+      return {
+        status: response.ok || response.status < 500 ? 'healthy' : 'unhealthy',
+        statusCode: response.status,
+        url,
+        checkedAt: new Date().toISOString()
+      };
+    } catch (_) {}
+
+    // Fallback to GET
+    try {
+      const controller = new AbortController();
+      const timeout = setTimeout(() => controller.abort(), 5000);
+      const response = await ctx.fetchT(url, { method: 'GET', signal: controller.signal, redirect: 'follow' });
+      clearTimeout(timeout);
+      return {
+        status: response.ok || response.status < 500 ? 'healthy' : 'unhealthy',
+        statusCode: response.status,
+        url,
+        checkedAt: new Date().toISOString()
+      };
+    } catch (e) {
+      return null; // Direct check completely failed
+    }
+  }
+
+  /**
+   * Check a URL through a Pylon relay. Returns health object or null on failure.
+   */
+  async function checkViaPylon(pylonConfig, url) {
+    if (!pylonConfig?.url) return null;
+    try {
+      const probeUrl = `${pylonConfig.url}/probe?url=${encodeURIComponent(url)}`;
+      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 {
+        status: data.status || 'unhealthy',
+        statusCode: data.statusCode,
+        responseTime: data.responseTime,
+        reason: data.reason,
+        url,
+        via: 'pylon',
+        checkedAt: data.checkedAt || new Date().toISOString()
+      };
+    } catch (_) {
+      return null;
+    }
+  }
+
   // ===== HEALTH / SERVICES =====
 
   // Check health of all services (performs live checks)
@@ -26,6 +90,7 @@ module.exports = function(ctx) {
     const servicesData = await ctx.servicesStateManager.read();
     const services = Array.isArray(servicesData) ? servicesData : servicesData.services || [];
     const health = {};
+    const pylonConfig = ctx.siteConfig?.pylon;
 
     // Check each service
     await Promise.all(services.map(async (service) => {
@@ -33,65 +98,35 @@ module.exports = function(ctx) {
       if (!serviceId) return;
 
       try {
-        let url = null;
-        let checkType = 'http';
-
-        // Determine URL to check
-        url = resolveServiceUrl(serviceId, service, ctx.siteConfig, ctx.buildServiceUrl);
-
+        const url = resolveServiceUrl(serviceId, service, ctx.siteConfig, ctx.buildServiceUrl);
         if (!url) {
           health[serviceId] = { status: 'unknown', reason: 'No URL configured' };
           return;
         }
 
-        // Perform health check with timeout
-        const controller = new AbortController();
-        const timeout = setTimeout(() => controller.abort(), 5000);
+        // 1. Try direct check
+        let result = await checkDirect(url);
+        if (result) {
+          health[serviceId] = result;
+          return;
+        }
 
-        try {
-          const response = await ctx.fetchT(url, {
-            method: 'HEAD',
-            signal: controller.signal,
-            redirect: 'follow'
-          });
-          clearTimeout(timeout);
-
-          health[serviceId] = {
-            status: response.ok || response.status < 500 ? 'healthy' : 'unhealthy',
-            statusCode: response.status,
-            url,
-            checkedAt: new Date().toISOString()
-          };
-        } catch (fetchError) {
-          clearTimeout(timeout);
-
-          // Try GET if HEAD fails
-          try {
-            const getController = new AbortController();
-            const getTimeout = setTimeout(() => getController.abort(), 5000);
-
-            const getResponse = await ctx.fetchT(url, {
-              method: 'GET',
-              signal: getController.signal,
-              redirect: 'follow'
-            });
-            clearTimeout(getTimeout);
-
-            health[serviceId] = {
-              status: getResponse.ok || getResponse.status < 500 ? 'healthy' : 'unhealthy',
-              statusCode: getResponse.status,
-              url,
-              checkedAt: new Date().toISOString()
-            };
-          } catch (e) {
-            health[serviceId] = {
-              status: 'unhealthy',
-              reason: e.name === 'AbortError' ? 'Timeout' : e.message,
-              url,
-              checkedAt: new Date().toISOString()
-            };
+        // 2. Direct failed — try through pylon relay
+        if (pylonConfig) {
+          result = await checkViaPylon(pylonConfig, url);
+          if (result) {
+            health[serviceId] = result;
+            return;
           }
         }
+
+        // 3. Both failed
+        health[serviceId] = {
+          status: 'unhealthy',
+          reason: pylonConfig ? 'Unreachable (direct + pylon)' : 'fetch failed',
+          url,
+          checkedAt: new Date().toISOString()
+        };
       } catch (e) {
         health[serviceId] = {
           status: 'error',
@@ -148,44 +183,62 @@ module.exports = function(ctx) {
 
     // Determine URL
     const url = resolveServiceUrl(serviceId, service, ctx.siteConfig, ctx.buildServiceUrl);
+    const pylonConfig = ctx.siteConfig?.pylon;
 
-    // Check health
-    const controller = new AbortController();
-    const timeout = setTimeout(() => controller.abort(), 5000);
-
-    try {
-      const response = await ctx.fetchT(url, {
-        method: 'GET',
-        signal: controller.signal,
-        redirect: 'follow'
-      });
-      clearTimeout(timeout);
-
-      res.json({
-        success: true,
-        serviceId,
-        health: {
-          status: response.ok || response.status < 500 ? 'healthy' : 'unhealthy',
-          statusCode: response.status,
-          url,
-          checkedAt: new Date().toISOString()
-        }
-      });
-    } catch (e) {
-      clearTimeout(timeout);
-      res.json({
-        success: true,
-        serviceId,
-        health: {
-          status: 'unhealthy',
-          reason: e.name === 'AbortError' ? 'Timeout' : e.message,
-          url,
-          checkedAt: new Date().toISOString()
-        }
-      });
+    // Try direct, then pylon relay
+    let result = await checkDirect(url);
+    if (!result && pylonConfig) {
+      result = await checkViaPylon(pylonConfig, url);
     }
+    if (!result) {
+      result = {
+        status: 'unhealthy',
+        reason: pylonConfig ? 'Unreachable (direct + pylon)' : 'fetch failed',
+        url,
+        checkedAt: new Date().toISOString()
+      };
+    }
+
+    res.json({ success: true, serviceId, health: result });
   }, 'health-service'));
 
+  // ===== HEALTH / PROBE (Pylon-compatible) =====
+
+  // Probe endpoint — lets this DashCaddy act as a pylon for other instances
+  router.get('/health/probe', ctx.asyncHandler(async (req, res) => {
+    const targetUrl = req.query.url;
+    if (!targetUrl) {
+      return ctx.errorResponse(res, 400, 'Missing ?url= parameter');
+    }
+    const result = await checkDirect(targetUrl);
+    res.json(result || {
+      status: 'unhealthy',
+      reason: 'fetch failed',
+      url: targetUrl,
+      checkedAt: new Date().toISOString()
+    });
+  }, 'health-probe'));
+
+  // Pylon status — check if the configured pylon is reachable
+  router.get('/health/pylon', ctx.asyncHandler(async (req, res) => {
+    const pylonConfig = ctx.siteConfig?.pylon;
+    if (!pylonConfig?.url) {
+      return res.json({ success: true, configured: false });
+    }
+    try {
+      const headers = {};
+      if (pylonConfig.key) headers['x-pylon-key'] = pylonConfig.key;
+      const response = await ctx.fetchT(`${pylonConfig.url}/health`, {
+        method: 'GET',
+        headers
+      }, 5000);
+      const data = await response.json();
+      res.json({ success: true, configured: true, reachable: true, pylon: data });
+    } catch (e) {
+      res.json({ success: true, configured: true, reachable: false, error: e.message });
+    }
+  }, 'health-pylon'));
+
   // ===== HEALTH / CA =====
 
   // Get CA certificate health status
diff --git a/dashcaddy-api/server.js b/dashcaddy-api/server.js
index 400e1cd..f04f281 100644
--- a/dashcaddy-api/server.js
+++ b/dashcaddy-api/server.js
@@ -157,6 +157,7 @@ function loadSiteConfig() {
       siteConfig.configurationType = raw.configurationType || 'homelab';
       siteConfig.domain = raw.domain || '';
       siteConfig.routingMode = raw.routingMode || 'subdomain';
+      siteConfig.pylon = raw.pylon || null; // { url, key? } — health check relay
     }
   } catch (e) {
     // log.error may not be assigned yet during initial module load