diff --git a/src/hooks/athena-sisyphus-only/index.test.ts b/src/hooks/athena-sisyphus-only/index.test.ts
index 056089497..2710d2f11 100644
--- a/src/hooks/athena-sisyphus-only/index.test.ts
+++ b/src/hooks/athena-sisyphus-only/index.test.ts
@@ -1,7 +1,11 @@
-import { describe, expect, it } from "bun:test"
+/// <reference types="bun-types" />
+
+import { afterEach, beforeEach, describe, expect, it } from "bun:test"
+import { mkdir, mkdtemp, rm, symlink, writeFile } from "node:fs/promises"
+import { join } from "node:path"
+import { tmpdir } from "node:os"
 import { isAllowedPath } from "./path-policy"
 import { isAthenaAgent } from "./agent-matcher"
-
 const WORKSPACE_ROOT = "/fake/workspace"
 
 describe("athena-sisyphus-only hook", () => {
@@ -65,6 +69,73 @@ describe("athena-sisyphus-only hook", () => {
         const absPath = `${WORKSPACE_ROOT}/.sisyphus/plans/test.md`
         expect(isAllowedPath(absPath, WORKSPACE_ROOT)).toBe(true)
       })
+
+      it("#then allows .sisyphus/plans/foo.md when .sisyphus doesn't exist yet (bootstrap)", () => {
+        expect(isAllowedPath(".sisyphus/plans/foo.md", WORKSPACE_ROOT)).toBe(true)
+      })
+
+      it("#then blocks ../etc/passwd even when .sisyphus doesn't exist", () => {
+        expect(isAllowedPath("../etc/passwd", WORKSPACE_ROOT)).toBe(false)
+      })
+
+      it("#then blocks ../../etc/passwd path traversal", () => {
+        expect(isAllowedPath("../../etc/passwd", WORKSPACE_ROOT)).toBe(false)
+      })
+    })
+
+    describe("#when checking symlink rejection", () => {
+      let tempWorkspaceRoot: string
+
+      beforeEach(async () => {
+        tempWorkspaceRoot = await mkdtemp(join(tmpdir(), "athena-sisyphus-only-"))
+        await mkdir(join(tempWorkspaceRoot, ".sisyphus", "tmp"), { recursive: true })
+        await mkdir(join(tempWorkspaceRoot, "outside", "nested"), { recursive: true })
+      })
+
+      afterEach(async () => {
+        await rm(tempWorkspaceRoot, { recursive: true, force: true })
+      })
+
+      it("#then rejects symlink inside .sisyphus/tmp/ pointing outside workspace", async () => {
+        const outsideFile = join(tempWorkspaceRoot, "outside", "secret.md")
+        const symlinkPath = join(tempWorkspaceRoot, ".sisyphus", "tmp", "escape.md")
+
+        await writeFile(outsideFile, "secret", "utf-8")
+        await symlink(outsideFile, symlinkPath)
+
+        expect(isAllowedPath(symlinkPath, tempWorkspaceRoot)).toBe(false)
+      })
+
+      it("#then rejects symlink inside .sisyphus/ pointing to /etc/passwd", async () => {
+        const symlinkPath = join(tempWorkspaceRoot, ".sisyphus", "passwd-link")
+
+        await symlink("/etc/passwd", symlinkPath)
+
+        expect(isAllowedPath(symlinkPath, tempWorkspaceRoot)).toBe(false)
+      })
+
+      it("#then allows a regular file inside .sisyphus/tmp/", async () => {
+        const regularFile = join(tempWorkspaceRoot, ".sisyphus", "tmp", "prompt.md")
+
+        await writeFile(regularFile, "prompt", "utf-8")
+
+        expect(isAllowedPath(regularFile, tempWorkspaceRoot)).toBe(true)
+      })
+
+      it("#then rejects a path with .. traversal", () => {
+        expect(isAllowedPath(".sisyphus/tmp/../../outside/secret.md", tempWorkspaceRoot)).toBe(false)
+      })
+
+      it("#then rejects nested symlinks that escape workspace", async () => {
+        const outsideNestedDir = join(tempWorkspaceRoot, "outside", "nested")
+        const nestedFile = join(outsideNestedDir, "secret.md")
+        const linkedDir = join(tempWorkspaceRoot, ".sisyphus", "tmp", "linked-dir")
+
+        await writeFile(nestedFile, "secret", "utf-8")
+        await symlink(outsideNestedDir, linkedDir)
+
+        expect(isAllowedPath(join(linkedDir, "secret.md"), tempWorkspaceRoot)).toBe(false)
+      })
     })
   })
 
diff --git a/src/hooks/athena-sisyphus-only/path-policy.ts b/src/hooks/athena-sisyphus-only/path-policy.ts
index c6f8da102..598fae612 100644
--- a/src/hooks/athena-sisyphus-only/path-policy.ts
+++ b/src/hooks/athena-sisyphus-only/path-policy.ts
@@ -1,4 +1,5 @@
-import { relative, resolve, isAbsolute } from "node:path"
+import { dirname, isAbsolute, relative, resolve } from "node:path"
+import { existsSync, realpathSync } from "node:fs"
 
 /**
  * Cross-platform path validator for Athena file writes.
@@ -9,20 +10,63 @@ import { relative, resolve, isAbsolute } from "node:path"
  * - Workspace confinement (blocks paths outside root or via traversal)
  * - No extension restriction: any file type is allowed inside .sisyphus/
  */
+function isWithinRoot(targetPath: string, rootPath: string): boolean {
+  const rel = relative(rootPath, targetPath)
+  return !((rel === ".." || rel.startsWith("../") || rel.startsWith("..\\")) || isAbsolute(rel))
+}
+
+function isWithinSisyphusSubtree(targetPath: string, rootPath: string): boolean {
+  const rel = relative(rootPath, targetPath)
+  return /(^|[\/\\])\.sisyphus([\/\\]|$)/i.test(rel)
+}
+
+function getNearestExistingPath(targetPath: string): string | null {
+  let current = targetPath
+  while (!existsSync(current)) {
+    const parent = dirname(current)
+    if (parent === current) {
+      return null
+    }
+    current = parent
+  }
+  return current
+}
+
 export function isAllowedPath(filePath: string, workspaceRoot: string): boolean {
-  // 1. Resolve to absolute path
-  const resolved = resolve(workspaceRoot, filePath)
+  const resolvedWorkspaceRoot = resolve(workspaceRoot)
+  const resolved = resolve(resolvedWorkspaceRoot, filePath)
 
-  // 2. Get relative path from workspace root
-  const rel = relative(workspaceRoot, resolved)
-
-  // 3. Reject if escapes root (traversal or absolute path)
-  if ((rel === ".." || rel.startsWith("../") || rel.startsWith("..\\")) || isAbsolute(rel)) {
+  const rel = relative(resolvedWorkspaceRoot, resolved)
+  if (!isWithinRoot(resolved, resolvedWorkspaceRoot)) {
     return false
   }
 
-  // 4. Check if .sisyphus is a complete path segment
-  if (!/(^|[\/\\])\.sisyphus[\/\\]/i.test(rel)) {
+  if (!/(^|[\/\\])\.sisyphus([\/\\]|$)/i.test(rel)) {
+    return false
+  }
+
+  if (!existsSync(resolvedWorkspaceRoot)) {
+    return true
+  }
+
+  const existingPath = getNearestExistingPath(resolved)
+  if (!existingPath) {
+    return false
+  }
+
+  const realWorkspaceRoot = realpathSync(resolvedWorkspaceRoot)
+  const realExistingPath = realpathSync(existingPath)
+  if (!isWithinRoot(realExistingPath, realWorkspaceRoot)) {
+    return false
+  }
+
+  // Allow bootstrap writes when nearest existing path is workspace root itself
+  // and the target path is within .sisyphus subtree
+  if (realExistingPath === realWorkspaceRoot) {
+    return isWithinSisyphusSubtree(resolved, realWorkspaceRoot)
+  }
+
+  if (!isWithinSisyphusSubtree(realExistingPath, realWorkspaceRoot)) {
     return false
   }