diff --git a/src/config/schema/hooks.ts b/src/config/schema/hooks.ts
index 00e04404e..6b0219f72 100644
--- a/src/config/schema/hooks.ts
+++ b/src/config/schema/hooks.ts
@@ -51,6 +51,7 @@ export const HookNameSchema = z.enum([
   "hashline-read-enhancer",
   "read-image-resizer",
   "todo-description-override",
+  "webfetch-redirect-guard",
 ])
 
 export type HookName = z.infer<typeof HookNameSchema>
diff --git a/src/hooks/index.ts b/src/hooks/index.ts
index abbf79bb7..8121f5097 100644
--- a/src/hooks/index.ts
+++ b/src/hooks/index.ts
@@ -52,3 +52,4 @@ export { createHashlineReadEnhancerHook } from "./hashline-read-enhancer";
 export { createJsonErrorRecoveryHook, JSON_ERROR_TOOL_EXCLUDE_LIST, JSON_ERROR_PATTERNS, JSON_ERROR_REMINDER } from "./json-error-recovery";
 export { createReadImageResizerHook } from "./read-image-resizer"
 export { createTodoDescriptionOverrideHook } from "./todo-description-override"
+export { createWebFetchRedirectGuardHook } from "./webfetch-redirect-guard"
diff --git a/src/hooks/webfetch-redirect-guard/constants.ts b/src/hooks/webfetch-redirect-guard/constants.ts
new file mode 100644
index 000000000..9befcf24d
--- /dev/null
+++ b/src/hooks/webfetch-redirect-guard/constants.ts
@@ -0,0 +1,11 @@
+export const DEFAULT_WEBFETCH_TIMEOUT_MS = 30_000
+export const MAX_WEBFETCH_TIMEOUT_MS = 120_000
+export const MAX_WEBFETCH_REDIRECTS = 10
+export const WEBFETCH_REDIRECT_GUARD_STALE_TIMEOUT_MS = 15 * 60 * 1000
+
+export const WEBFETCH_REDIRECT_ERROR_PATTERNS = [
+  /redirected too many times/i,
+  /too many redirects/i,
+] as const
+
+export const WEBFETCH_REDIRECT_STATUSES = new Set([301, 302, 303, 307, 308])
diff --git a/src/hooks/webfetch-redirect-guard/hook.ts b/src/hooks/webfetch-redirect-guard/hook.ts
new file mode 100644
index 000000000..aec40aa18
--- /dev/null
+++ b/src/hooks/webfetch-redirect-guard/hook.ts
@@ -0,0 +1,119 @@
+import type { PluginInput } from "@opencode-ai/plugin"
+import { log } from "../../shared"
+import {
+  MAX_WEBFETCH_REDIRECTS,
+  WEBFETCH_REDIRECT_ERROR_PATTERNS,
+  WEBFETCH_REDIRECT_GUARD_STALE_TIMEOUT_MS,
+} from "./constants"
+import {
+  resolveWebFetchRedirects,
+  type WebFetchFormat,
+} from "./redirect-resolution"
+
+type ToolExecuteInput = { tool: string; sessionID: string; callID: string }
+type ToolExecuteBeforeOutput = { args: Record<string, unknown> }
+type ToolExecuteAfterOutput = {
+  title: string
+  output: string
+  metadata: Record<string, unknown>
+}
+
+type PendingRedirectFailure = {
+  originalUrl: string
+  storedAt: number
+}
+
+function makeKey(sessionID: string, callID: string): string {
+  return `${sessionID}:${callID}`
+}
+
+function isWebFetchTool(toolName: string): boolean {
+  return toolName.toLowerCase() === "webfetch"
+}
+
+function getWebFetchUrl(args: Record<string, unknown>): string | undefined {
+  return typeof args.url === "string" && args.url.length > 0 ? args.url : undefined
+}
+
+function getWebFetchFormat(args: Record<string, unknown>): WebFetchFormat {
+  return args.format === "text" || args.format === "html" ? args.format : "markdown"
+}
+
+function getTimeoutSeconds(args: Record<string, unknown>): number | undefined {
+  return typeof args.timeout === "number" && Number.isFinite(args.timeout) ? args.timeout : undefined
+}
+
+function cleanupStaleEntries(pendingFailures: Map<string, PendingRedirectFailure>): void {
+  const now = Date.now()
+  for (const [key, value] of pendingFailures) {
+    if (now - value.storedAt > WEBFETCH_REDIRECT_GUARD_STALE_TIMEOUT_MS) {
+      pendingFailures.delete(key)
+    }
+  }
+}
+
+function isRedirectLoopError(output: string): boolean {
+  return WEBFETCH_REDIRECT_ERROR_PATTERNS.some((pattern) => pattern.test(output))
+}
+
+function buildRedirectLimitMessage(url?: string): string {
+  const suffix = url ? ` for ${url}` : ""
+  return `Error: WebFetch failed: exceeded maximum redirects (${MAX_WEBFETCH_REDIRECTS})${suffix}`
+}
+
+export function createWebFetchRedirectGuardHook(_ctx: PluginInput) {
+  const pendingFailures = new Map<string, PendingRedirectFailure>()
+
+  return {
+    "tool.execute.before": async (input: ToolExecuteInput, output: ToolExecuteBeforeOutput) => {
+      if (!isWebFetchTool(input.tool)) return
+
+      const url = getWebFetchUrl(output.args)
+      if (!url) return
+
+      cleanupStaleEntries(pendingFailures)
+
+      try {
+        const resolution = await resolveWebFetchRedirects({
+          url,
+          format: getWebFetchFormat(output.args),
+          timeoutSeconds: getTimeoutSeconds(output.args),
+        })
+
+        if (resolution.type === "resolved") {
+          output.args.url = resolution.url
+          return
+        }
+
+        pendingFailures.set(makeKey(input.sessionID, input.callID), {
+          originalUrl: url,
+          storedAt: Date.now(),
+        })
+      } catch (error) {
+        log("[webfetch-redirect-guard] Failed to pre-resolve redirects", {
+          sessionID: input.sessionID,
+          callID: input.callID,
+          url,
+          error,
+        })
+      }
+    },
+
+    "tool.execute.after": async (input: ToolExecuteInput, output: ToolExecuteAfterOutput) => {
+      if (!isWebFetchTool(input.tool)) return
+      if (typeof output.output !== "string") return
+
+      const key = makeKey(input.sessionID, input.callID)
+      const pendingFailure = pendingFailures.get(key)
+      if (pendingFailure) {
+        pendingFailures.delete(key)
+        output.output = buildRedirectLimitMessage(pendingFailure.originalUrl)
+        return
+      }
+
+      if (isRedirectLoopError(output.output)) {
+        output.output = buildRedirectLimitMessage()
+      }
+    },
+  }
+}
diff --git a/src/hooks/webfetch-redirect-guard/index.test.ts b/src/hooks/webfetch-redirect-guard/index.test.ts
new file mode 100644
index 000000000..3d53b1f9e
--- /dev/null
+++ b/src/hooks/webfetch-redirect-guard/index.test.ts
@@ -0,0 +1,170 @@
+import { afterEach, describe, expect, it } from "bun:test"
+import { createWebFetchRedirectGuardHook } from "./hook"
+
+const originalFetch = globalThis.fetch
+
+type FetchCall = {
+  url: string
+  init?: RequestInit
+}
+
+function createInput(tool = "webfetch") {
+  return {
+    tool,
+    sessionID: "ses_test",
+    callID: "call_test",
+  }
+}
+
+function createBeforeOutput(url: string, format: "markdown" | "text" | "html" = "markdown") {
+  return {
+    args: {
+      url,
+      format,
+    },
+  }
+}
+
+function createAfterOutput(outputText: string) {
+  return {
+    title: "WebFetch",
+    output: outputText,
+    metadata: {},
+  }
+}
+
+function getHeaderValue(headers: RequestInit["headers"], key: string): string | undefined {
+  if (!headers) return undefined
+  if (headers instanceof Headers) return headers.get(key) ?? undefined
+  if (Array.isArray(headers)) {
+    const match = headers.find(([name]) => name.toLowerCase() === key.toLowerCase())
+    return match?.[1]
+  }
+
+  const match = Object.entries(headers).find(([name]) => name.toLowerCase() === key.toLowerCase())
+  return typeof match?.[1] === "string" ? match[1] : undefined
+}
+
+function createFetchMock(
+  implementation: (input: RequestInfo | URL, init?: RequestInit) => Promise<Response>,
+): typeof fetch {
+  return Object.assign(implementation, {
+    preconnect: originalFetch.preconnect,
+  })
+}
+
+afterEach(() => {
+  globalThis.fetch = originalFetch
+})
+
+describe("createWebFetchRedirectGuardHook", () => {
+  describe("#given the webfetch tool", () => {
+    describe("#when the URL redirects once", () => {
+      it("#then should replace args.url with the resolved final URL", async () => {
+        const calls: FetchCall[] = []
+        globalThis.fetch = createFetchMock(async (input: RequestInfo | URL, init?: RequestInit) => {
+          calls.push({ url: String(input), init })
+
+          if (calls.length === 1) {
+            return new Response(null, {
+              status: 302,
+              headers: { Location: "https://example.com/final" },
+            })
+          }
+
+          return new Response("ok", { status: 200 })
+        })
+
+        const hook = createWebFetchRedirectGuardHook({} as never)
+        const input = createInput()
+        const output = createBeforeOutput("https://example.com/start")
+
+        await hook["tool.execute.before"](input, output)
+
+        expect(output.args.url).toBe("https://example.com/final")
+        expect(getHeaderValue(calls[0]?.init?.headers, "accept")).toContain("text/markdown")
+        expect(getHeaderValue(calls[0]?.init?.headers, "user-agent")).toContain("Mozilla/5.0")
+        expect(getHeaderValue(calls[0]?.init?.headers, "accept-language")).toBe("en-US,en;q=0.9")
+      })
+    })
+
+    describe("#when the redirect location is relative", () => {
+      it("#then should resolve the location against the current URL", async () => {
+        let callCount = 0
+        globalThis.fetch = createFetchMock(async (_input: RequestInfo | URL) => {
+          callCount += 1
+
+          if (callCount === 1) {
+            return new Response(null, {
+              status: 301,
+              headers: { Location: "/docs/final" },
+            })
+          }
+
+          return new Response("ok", { status: 200 })
+        })
+
+        const hook = createWebFetchRedirectGuardHook({} as never)
+        const input = createInput()
+        const output = createBeforeOutput("https://example.com/docs/start")
+
+        await hook["tool.execute.before"](input, output)
+
+        expect(output.args.url).toBe("https://example.com/docs/final")
+      })
+    })
+
+    describe("#when the redirect chain exceeds the limit", () => {
+      it("#then should rewrite the raw redirect-loop error to a clear message", async () => {
+        globalThis.fetch = createFetchMock(async () => {
+          return new Response(null, {
+            status: 302,
+            headers: { Location: "/loop" },
+          })
+        })
+
+        const hook = createWebFetchRedirectGuardHook({} as never)
+        const input = createInput()
+        const beforeOutput = createBeforeOutput("https://example.com/loop")
+        const afterOutput = createAfterOutput(
+          "Error: The response redirected too many times. For more information, pass `verbose: true` in the second argument to fetch()",
+        )
+
+        await hook["tool.execute.before"](input, beforeOutput)
+        await hook["tool.execute.after"](input, afterOutput)
+
+        expect(afterOutput.output).toBe(
+          "Error: WebFetch failed: exceeded maximum redirects (10) for https://example.com/loop",
+        )
+      })
+    })
+
+    describe("#when a raw redirect-loop error arrives without tracked state", () => {
+      it("#then should still normalize the message", async () => {
+        const hook = createWebFetchRedirectGuardHook({} as never)
+        const input = createInput()
+        const output = createAfterOutput("error: too many redirects")
+
+        await hook["tool.execute.after"](input, output)
+
+        expect(output.output).toBe(
+          "Error: WebFetch failed: exceeded maximum redirects (10)",
+        )
+      })
+    })
+  })
+
+  describe("#given a non-webfetch tool", () => {
+    describe("#when the hook runs", () => {
+      it("#then should leave the args untouched", async () => {
+        const hook = createWebFetchRedirectGuardHook({} as never)
+        const input = createInput("grep")
+        const output = createBeforeOutput("https://example.com/start")
+
+        await hook["tool.execute.before"](input, output)
+
+        expect(output.args.url).toBe("https://example.com/start")
+      })
+    })
+  })
+})
diff --git a/src/hooks/webfetch-redirect-guard/index.ts b/src/hooks/webfetch-redirect-guard/index.ts
new file mode 100644
index 000000000..372e35f1e
--- /dev/null
+++ b/src/hooks/webfetch-redirect-guard/index.ts
@@ -0,0 +1 @@
+export { createWebFetchRedirectGuardHook } from "./hook"
diff --git a/src/hooks/webfetch-redirect-guard/redirect-resolution.ts b/src/hooks/webfetch-redirect-guard/redirect-resolution.ts
new file mode 100644
index 000000000..ca23c2a67
--- /dev/null
+++ b/src/hooks/webfetch-redirect-guard/redirect-resolution.ts
@@ -0,0 +1,89 @@
+import {
+  DEFAULT_WEBFETCH_TIMEOUT_MS,
+  MAX_WEBFETCH_REDIRECTS,
+  MAX_WEBFETCH_TIMEOUT_MS,
+  WEBFETCH_REDIRECT_STATUSES,
+} from "./constants"
+
+export type WebFetchFormat = "markdown" | "text" | "html"
+
+type RedirectResolutionParams = {
+  url: string
+  format: WebFetchFormat
+  timeoutSeconds?: number
+}
+
+export type RedirectResolutionResult =
+  | { type: "resolved"; url: string }
+  | { type: "exceeded"; url: string; maxRedirects: number }
+
+function buildAcceptHeader(format: WebFetchFormat): string {
+  switch (format) {
+    case "markdown":
+      return "text/markdown;q=1.0, text/x-markdown;q=0.9, text/plain;q=0.8, text/html;q=0.7, */*;q=0.1"
+    case "text":
+      return "text/plain;q=1.0, text/markdown;q=0.9, text/html;q=0.8, */*;q=0.1"
+    case "html":
+      return "text/html;q=1.0, application/xhtml+xml;q=0.9, text/plain;q=0.8, text/markdown;q=0.7, */*;q=0.1"
+  }
+}
+
+function buildWebFetchHeaders(format: WebFetchFormat): Record<string, string> {
+  return {
+    "User-Agent":
+      "Mozilla/5.0 (Windows NT 10.0; Win64; x64) AppleWebKit/537.36 (KHTML, like Gecko) Chrome/143.0.0.0 Safari/537.36",
+    Accept: buildAcceptHeader(format),
+    "Accept-Language": "en-US,en;q=0.9",
+  }
+}
+
+function normalizeTimeoutMs(timeoutSeconds?: number): number {
+  if (typeof timeoutSeconds !== "number" || !Number.isFinite(timeoutSeconds) || timeoutSeconds <= 0) {
+    return DEFAULT_WEBFETCH_TIMEOUT_MS
+  }
+
+  return Math.min(timeoutSeconds * 1000, MAX_WEBFETCH_TIMEOUT_MS)
+}
+
+function resolveRedirectLocation(currentUrl: string, location: string): string {
+  return new URL(location, currentUrl).toString()
+}
+
+export async function resolveWebFetchRedirects(
+  params: RedirectResolutionParams,
+): Promise<RedirectResolutionResult> {
+  const timeoutMs = normalizeTimeoutMs(params.timeoutSeconds)
+  const signal = AbortSignal.timeout(timeoutMs)
+  const headers = buildWebFetchHeaders(params.format)
+
+  let currentUrl = params.url
+  let redirectCount = 0
+
+  while (true) {
+    const response = await fetch(currentUrl, {
+      headers,
+      redirect: "manual",
+      signal,
+    })
+
+    if (!WEBFETCH_REDIRECT_STATUSES.has(response.status)) {
+      return { type: "resolved", url: currentUrl }
+    }
+
+    const location = response.headers.get("location")
+    if (!location) {
+      return { type: "resolved", url: currentUrl }
+    }
+
+    if (redirectCount >= MAX_WEBFETCH_REDIRECTS) {
+      return {
+        type: "exceeded",
+        url: params.url,
+        maxRedirects: MAX_WEBFETCH_REDIRECTS,
+      }
+    }
+
+    currentUrl = resolveRedirectLocation(currentUrl, location)
+    redirectCount += 1
+  }
+}
diff --git a/src/plugin/hooks/create-tool-guard-hooks.ts b/src/plugin/hooks/create-tool-guard-hooks.ts
index 1c79f6949..46f724cf7 100644
--- a/src/plugin/hooks/create-tool-guard-hooks.ts
+++ b/src/plugin/hooks/create-tool-guard-hooks.ts
@@ -15,6 +15,7 @@ import {
   createReadImageResizerHook,
   createJsonErrorRecoveryHook,
   createTodoDescriptionOverrideHook,
+  createWebFetchRedirectGuardHook,
 } from "../../hooks"
 import {
   getOpenCodeVersion,
@@ -37,6 +38,7 @@ export type ToolGuardHooks = {
   jsonErrorRecovery: ReturnType<typeof createJsonErrorRecoveryHook> | null
   readImageResizer: ReturnType<typeof createReadImageResizerHook> | null
   todoDescriptionOverride: ReturnType<typeof createTodoDescriptionOverrideHook> | null
+  webfetchRedirectGuard: ReturnType<typeof createWebFetchRedirectGuardHook> | null
 }
 
 export function createToolGuardHooks(args: {
@@ -117,6 +119,10 @@ export function createToolGuardHooks(args: {
     ? safeHook("todo-description-override", () => createTodoDescriptionOverrideHook())
     : null
 
+  const webfetchRedirectGuard = isHookEnabled("webfetch-redirect-guard")
+    ? safeHook("webfetch-redirect-guard", () => createWebFetchRedirectGuardHook(ctx))
+    : null
+
   return {
     commentChecker,
     toolOutputTruncator,
@@ -130,5 +136,6 @@ export function createToolGuardHooks(args: {
     jsonErrorRecovery,
     readImageResizer,
     todoDescriptionOverride,
+    webfetchRedirectGuard,
   }
 }
diff --git a/src/plugin/tool-execute-after.ts b/src/plugin/tool-execute-after.ts
index 0cc986b7d..fb1be3aa4 100644
--- a/src/plugin/tool-execute-after.ts
+++ b/src/plugin/tool-execute-after.ts
@@ -125,6 +125,7 @@ export function createToolExecuteAfterHandler(args: {
       await hooks.taskResumeInfo?.["tool.execute.after"]?.(input, output)
       await hooks.readImageResizer?.["tool.execute.after"]?.(input, output)
       await hooks.hashlineReadEnhancer?.["tool.execute.after"]?.(input, output)
+      await hooks.webfetchRedirectGuard?.["tool.execute.after"]?.(input, output)
       await hooks.jsonErrorRecovery?.["tool.execute.after"]?.(input, output)
     }
 
diff --git a/src/plugin/tool-execute-before.ts b/src/plugin/tool-execute-before.ts
index 5d4f2c86e..e5aad89a0 100644
--- a/src/plugin/tool-execute-before.ts
+++ b/src/plugin/tool-execute-before.ts
@@ -50,6 +50,7 @@ export function createToolExecuteBeforeHandler(args: {
     await hooks.directoryReadmeInjector?.["tool.execute.before"]?.(input, output)
     await hooks.rulesInjector?.["tool.execute.before"]?.(input, output)
     await hooks.tasksTodowriteDisabler?.["tool.execute.before"]?.(input, output)
+    await hooks.webfetchRedirectGuard?.["tool.execute.before"]?.(input, output)
     await hooks.prometheusMdOnly?.["tool.execute.before"]?.(input, output)
     await hooks.sisyphusJuniorNotepad?.["tool.execute.before"]?.(input, output)
     await hooks.atlasHook?.["tool.execute.before"]?.(input, output)