diff --git a/mcp/src/config.ts b/mcp/src/config.ts
index 34484822..ed70bbc1 100644
--- a/mcp/src/config.ts
+++ b/mcp/src/config.ts
@@ -9,6 +9,7 @@ export interface HonchoConfig {
 
 export interface Env {
   HONCHO_API_URL?: string;
+  ALERT_WEBHOOK_URL?: string;
 }
 
 /**
diff --git a/mcp/src/index.ts b/mcp/src/index.ts
index 52123dee..3c679dd8 100644
--- a/mcp/src/index.ts
+++ b/mcp/src/index.ts
@@ -20,6 +20,7 @@ const CORS_HEADERS = {
 };
 
 const PROTECTED_RESOURCE_PATH = "/.well-known/oauth-protected-resource";
+const HEALTHCHECK_TIMEOUT_MS = 15_000;
 
 function resourceUrl(request: Request): string {
   return new URL(request.url).origin;
@@ -30,6 +31,41 @@ function authorizationServer(env: Env): string {
 }
 
 export default {
+  // Probes the authorization server API to confirm it is reachable and healthy.
+  async scheduled(
+    _controller: ScheduledController,
+    env: Env,
+    _executionCtx: ExecutionContext,
+  ): Promise<void> {
+    const upstream = `${authorizationServer(env)}/health`;
+
+    let failure: string | null = null;
+    try {
+      const response = await fetch(upstream, {
+        signal: AbortSignal.timeout(HEALTHCHECK_TIMEOUT_MS),
+      });
+      if (!response.ok) failure = `HTTP ${response.status}`;
+    } catch (e) {
+      failure = e instanceof Error ? e.message : String(e);
+    }
+    if (!failure) return;
+
+    console.error(`healthcheck failed: ${upstream} — ${failure}`);
+    if (!env.ALERT_WEBHOOK_URL) return;
+
+    const alertResponse = await fetch(env.ALERT_WEBHOOK_URL, {
+      method: "POST",
+      headers: { "Content-Type": "application/json" },
+      body: JSON.stringify({
+        content: `🚨 honcho-mcp cannot reach upstream API (${upstream}): ${failure}`,
+      }),
+      signal: AbortSignal.timeout(HEALTHCHECK_TIMEOUT_MS),
+    });
+    if (!alertResponse.ok) {
+      throw new Error(`alert webhook failed: HTTP ${alertResponse.status}`);
+    }
+  },
+
   async fetch(
     request: Request,
     env: Env,
diff --git a/mcp/wrangler.toml b/mcp/wrangler.toml
index 987b0b6b..04fe7894 100644
--- a/mcp/wrangler.toml
+++ b/mcp/wrangler.toml
@@ -8,6 +8,10 @@ rules = [
   { type = "Text", globs = ["**/*.md"], fallthrough = true },
 ]
 
+# Executes the scheduled() handler
+[triggers]
+crons = ["*/5 * * * *"]
+
 [env.production]
 name = "honcho-mcp"