diff --git a/CHANGELOG.md b/CHANGELOG.md
index a9b5122..ef896fb 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -4,3 +4,4 @@
 
 - Fix ClawHub appeals accepting client-supplied account context, and revalidate new and pending appeals against the authenticated GitHub applicant before unbanning. Thanks @SebTardif for the report and intake fix.
 - Reject crafted GitHub summary owner/repository paths before authenticated requests while preserving configured installation access. Thanks @SebTardif for the report and path validation fix.
+- Avoid duplicate channel webhooks when concurrent automod events reach an empty cache in the same Worker instance.
diff --git a/README.md b/README.md
index 43aeafe..6240ad6 100644
--- a/README.md
+++ b/README.md
@@ -140,6 +140,10 @@ The Worker must have the matching public key:
 bunx wrangler secret put FORWARDER_PUBLIC_KEY
 ```
 
+## Automod webhooks
+
+Concurrent automod events in the same Worker instance share the channel webhook lookup and creation. Failed attempts are cleared so a later event can retry; successful webhooks retain the existing 15-minute cache. Separate Worker instances still manage their own caches.
+
 ## Notes
 
 - Answer Overflow base URL is hardcoded to `https://www.answeroverflow.com`.
diff --git a/src/utils/channelWebhook.ts b/src/utils/channelWebhook.ts
index ec6e4fc..8434eaa 100644
--- a/src/utils/channelWebhook.ts
+++ b/src/utils/channelWebhook.ts
@@ -7,6 +7,7 @@ import {
 } from "@buape/carbon"
 
 const webhookCache = new Map<string, { webhook: Webhook; fetchedAt: number }>()
+const pendingWebhooks = new Map<string, Promise<Webhook>>()
 const webhookCacheTtlMs = 15 * 60 * 1000
 
 const cleanupWebhookCache = () => {
@@ -42,17 +43,30 @@ export const getOrCreateChannelWebhook = async (
 		return cached.webhook
 	}
 
-	const existingWebhooks = await fetchChannelWebhooks(client, channelId)
-	const usableWebhook = existingWebhooks.find((webhook) => webhook.token)
-	const webhookData = usableWebhook ?? (await createChannelWebhook(client, channelId, name))
-
-	if (!webhookData.token) {
-		throw new Error("Webhook token missing for channel repost")
+	const pending = pendingWebhooks.get(channelId)
+	if (pending) {
+		return pending
 	}
 
-	const webhook = new Webhook({ id: webhookData.id, token: webhookData.token })
-	webhookCache.set(channelId, { webhook, fetchedAt: Date.now() })
-	return webhook
+	const request = (async () => {
+		const existingWebhooks = await fetchChannelWebhooks(client, channelId)
+		const usableWebhook = existingWebhooks.find((webhook) => webhook.token)
+		const webhookData = usableWebhook ?? (await createChannelWebhook(client, channelId, name))
+
+		if (!webhookData.token) {
+			throw new Error("Webhook token missing for channel repost")
+		}
+
+		const webhook = new Webhook({ id: webhookData.id, token: webhookData.token })
+		webhookCache.set(channelId, { webhook, fetchedAt: Date.now() })
+		return webhook
+	})()
+	pendingWebhooks.set(channelId, request)
+	try {
+		return await request
+	} finally {
+		pendingWebhooks.delete(channelId)
+	}
 }
 
 export const sendWebhookMessage = async (
diff --git a/tests/channelWebhook.test.ts b/tests/channelWebhook.test.ts
new file mode 100644
index 0000000..e906030
--- /dev/null
+++ b/tests/channelWebhook.test.ts
@@ -0,0 +1,72 @@
+import { describe, expect, it, mock } from "bun:test"
+import type { Client } from "@buape/carbon"
+import { getOrCreateChannelWebhook } from "../src/utils/channelWebhook.js"
+
+const webhookData = { id: "123", token: "synthetic-webhook-token" }
+const makeClient = (get: () => Promise<unknown>, post = async () => webhookData) => {
+	const rest = { get: mock(get), post: mock(post) }
+	return { client: { rest } as unknown as Client, rest }
+}
+
+describe("channel webhook cache", () => {
+	it("shares lookup and creation among simultaneous callers", async () => {
+		const { client, rest } = makeClient(async () => [])
+		const webhooks = await Promise.all(Array.from({ length: 20 }, () =>
+			getOrCreateChannelWebhook(client, "concurrent-create")
+		))
+		expect(rest.get).toHaveBeenCalledTimes(1)
+		expect(rest.post).toHaveBeenCalledTimes(1)
+		expect(new Set(webhooks).size).toBe(1)
+		expect(await getOrCreateChannelWebhook(client, "concurrent-create")).toBe(webhooks[0])
+		expect(rest.get).toHaveBeenCalledTimes(1)
+	})
+
+	it("shares an existing webhook without creating another", async () => {
+		const { client, rest } = makeClient(async () => [webhookData])
+		const webhooks = await Promise.all([
+			getOrCreateChannelWebhook(client, "concurrent-existing"),
+			getOrCreateChannelWebhook(client, "concurrent-existing")
+		])
+		expect(rest.get).toHaveBeenCalledTimes(1)
+		expect(rest.post).not.toHaveBeenCalled()
+		expect(webhooks[0]).toBe(webhooks[1])
+	})
+
+	for (const stage of ["lookup", "create", "missing-token"] as const) {
+		it(`releases failed ${stage} attempts so later events can retry`, async () => {
+			let fail = true
+			const { client, rest } = makeClient(async () => {
+				if (fail && stage === "lookup") throw new Error("lookup unavailable")
+				return []
+			}, async () => {
+				if (fail && stage === "create") throw new Error("create unavailable")
+				return fail && stage === "missing-token" ? { id: "123", token: "" } : webhookData
+			})
+			const channel = `retry-${stage}`
+			const results = await Promise.allSettled([
+				getOrCreateChannelWebhook(client, channel),
+				getOrCreateChannelWebhook(client, channel)
+			])
+			expect(results.map((result) => result.status)).toEqual(["rejected", "rejected"])
+			expect(rest.get).toHaveBeenCalledTimes(1)
+			fail = false
+			expect((await getOrCreateChannelWebhook(client, channel)).id).toBe(webhookData.id)
+			expect(rest.get).toHaveBeenCalledTimes(2)
+		})
+	}
+
+	it("does not block another channel behind a pending lookup", async () => {
+		let release = (_: unknown[]) => {}
+		const pending = new Promise<unknown[]>((resolve) => { release = resolve })
+		const slow = makeClient(() => pending)
+		const fast = makeClient(async () => [webhookData])
+		const slowRequest = getOrCreateChannelWebhook(slow.client, "slow-channel")
+		try {
+			expect((await getOrCreateChannelWebhook(fast.client, "fast-channel")).id).toBe(webhookData.id)
+			expect(slow.rest.post).not.toHaveBeenCalled()
+		} finally {
+			release([])
+			await slowRequest
+		}
+	})
+})