diff --git a/bot/src/config.ts b/bot/src/config.ts
index 595e3c3..9bbe25d 100644
--- a/bot/src/config.ts
+++ b/bot/src/config.ts
@@ -3,6 +3,10 @@
 
 export interface Env {
   BOT_TOKEN: string; // wrangler secret (D-15) — Telegram Bot API token from @BotFather
+  // WEBHOOK_SECRET MUST be a non-empty secret (D-15) — /telegram/webhook
+  // fails closed at request time when missing/empty (WR-02), refusing all
+  // deliveries rather than letting grammY's secret check degrade to
+  // accept-everything.
   WEBHOOK_SECRET: string; // wrangler secret (D-15) — value Telegram echoes in X-Telegram-Bot-Api-Secret-Token
   chat_sessions: KVNamespace; // TTL-only namespace — first durable KV namespace (PRIV-02)
 }
diff --git a/bot/src/webhook.ts b/bot/src/webhook.ts
index e75b721..1385a24 100644
--- a/bot/src/webhook.ts
+++ b/bot/src/webhook.ts
@@ -6,8 +6,12 @@
  *     the configured secret token — Telegram's updates must carry
  *     X-Telegram-Bot-Api-Secret-Token = env.WEBHOOK_SECRET or they are 401'd
  *     by a constant-time compare BEFORE any bot processing or KV touch
- *     (T-02-03). The bot is instantiated per request because the token only
- *     arrives with `env` (research-verified Workers pattern).
+ *     (T-02-03). FAIL-CLOSED (WR-02): if the WEBHOOK_SECRET binding is
+ *     missing/empty at request time, the route rejects outright — grammY's
+ *     compareSecretToken silently accepts EVERY request when its secret is
+ *     undefined, so an unarmed binding must never reach it. The bot is
+ *     instantiated per request because the token only arrives with `env`
+ *     (research-verified Workers pattern).
  *   POST /api/session       → the phase's security gate (T-02-01): the caller
  *     posts a verbatim Telegram.WebApp.initData string — capped at 4 KB
  *     (WR-01: over-cap bodies are rejected 413 before any parsing; real
@@ -18,7 +22,8 @@
  *     this endpoint adds no extra branch and no extra write path (T-02-06).
  * Anything else → 404.
  *
- * D-14: the ONLY log statement is category-only (malformed/tampered/stale) —
+ * D-14: the ONLY log statements are category-only — malformed/tampered/stale
+ * on the initData gate, misconfigured on the fail-closed webhook gate —
  * never the raw payload, never user ids, never timestamps. Rejection
  * responses carry the category only.
  * D-17: no secret is ever logged or echoed; the bot token / webhook secret
@@ -34,6 +39,17 @@ export default {
   async fetch(req: Request, env: Env, _ctx: ExecutionContext): Promise<Response> {
     const url = new URL(req.url);
     if (url.pathname === "/telegram/webhook") {
+      // WR-02 fail-closed: grammY's compareSecretToken accepts EVERY request
+      // when its secret is undefined (research-confirmed runtime behavior,
+      // convenience/webhook.js). A WEBHOOK_SECRET binding left unarmed after
+      // deploy would therefore silently disable webhook authentication and
+      // admit unsigned POSTs that inject fabricated updates. This guard runs
+      // BEFORE createBot/webhookCallback; the rejection is a constant 500
+      // and the log carries the category only.
+      if (!env.WEBHOOK_SECRET) {
+        console.log("[webhook] rejected: misconfigured");
+        return new Response("Server misconfigured", { status: 500 });
+      }
       const bot = createBot(env); // env-bound token → per-request instantiation
       const cb = webhookCallback(bot, "cloudflare-mod", undefined, undefined, env.WEBHOOK_SECRET);
       return cb(req);
diff --git a/bot/test/webhook.test.mjs b/bot/test/webhook.test.mjs
index 7276bdc..86efe2b 100644
--- a/bot/test/webhook.test.mjs
+++ b/bot/test/webhook.test.mjs
@@ -13,7 +13,7 @@
  * live Bot API. Armed-secret behavior is verified by the live smokes in
  * plan 02-03 instead.
  *
- * Cases (WR-01 body cap, T-02-01 gate):
+ * Cases (WR-01 body cap, WR-02 fail-closed gate, T-02-01 gate):
  *   WK1  POST valid initData under the cap → 200 {token: uuid};
  *        exactly two TTL-carrying KV writes (900 s)
  *   WK2  POST an over-cap (4 KB+) but VALIDLY SIGNED initData → 413
@@ -24,6 +24,9 @@
  *   WK3  declared-length 999999 + unreadable body stream → 413 resolved
  *        WITHOUT pulling the stream (the pre-read check refuses to buffer)
  *   WK4  GET /api/session → 405 (the cap logic never runs on GET)
+ *   WK5  unarmed WEBHOOK_SECRET → /telegram/webhook rejects CLOSED with a
+ *        constant 500 BEFORE grammY's compareSecretToken (which would
+ *        accept every request once the secret is undefined — WR-02)
  */
 import { strict as assert } from "node:assert";
 import { createHmac } from "node:crypto";
@@ -185,3 +188,17 @@ test("WK4 GET /api/session → 405", async () => {
   const res = await handler(req, makeEnv(makeKV()), {});
   assert.equal(res.status, 405);
 });
+
+/* ————— WK5 — WR-02 fail-closed webhook gate ————— */
+
+test("WK5 unarmed WEBHOOK_SECRET ('') → webhook rejects CLOSED with a constant 500, no bot run, no KV touch", async () => {
+  const env = { BOT_TOKEN: TEST_TOKEN, WEBHOOK_SECRET: "", chat_sessions: undefined };
+  const req = () => new Request("https://host/telegram/webhook", { method: "POST", body: '{\"update_id\":1}' });
+  const res1 = await handler(req(), env, {});
+  const res2 = await handler(req(), env, {});
+  assert.equal(res1.status, 500, "missing binding must fail closed, not fall through to grammY's accept-everything compare");
+  assert.equal(res2.status, 500, "the rejection is constant across calls");
+  assert.equal(await res1.text(), "Server misconfigured");
+  assert.equal(await res2.text(), "Server misconfigured");
+  assert.ok(env.chat_sessions === undefined, "the guard fired before any storage or bot wiring was needed");
+});