diff --git a/apps/cli/src/commands/add-skill.ts b/apps/cli/src/commands/add-skill.ts
index dd486de0e..6339c16d8 100644
--- a/apps/cli/src/commands/add-skill.ts
+++ b/apps/cli/src/commands/add-skill.ts
@@ -3,6 +3,7 @@ import {
   lstatSync,
   mkdirSync,
   readlinkSync,
+  rmSync,
   symlinkSync,
   unlinkSync,
   writeFileSync,
@@ -91,6 +92,14 @@ const downloadSkill = async (skillDir: string): Promise<boolean> => {
   }
 };
 
+const getPathStats = (path: string) => {
+  try {
+    return lstatSync(path);
+  } catch {
+    return undefined;
+  }
+};
+
 const selectAgents = async (agents: readonly SupportedAgent[], nonInteractive: boolean) => {
   if (nonInteractive) return [...agents];
 
@@ -114,18 +123,21 @@ const selectAgents = async (agents: readonly SupportedAgent[], nonInteractive: b
   return (response.agents ?? []) as SupportedAgent[];
 };
 
-const ensureAgentSymlink = (projectRoot: string, agent: SupportedAgent): boolean | string => {
+export const ensureAgentSymlink = (projectRoot: string, agent: SupportedAgent): boolean | string => {
   const skillSourceDir = join(projectRoot, AGENTS_SKILLS_DIR, SKILL_NAME);
   const agentSkillDir = join(projectRoot, toSkillDir(agent));
   const symlinkPath = join(agentSkillDir, SKILL_NAME);
   const targetPath = relative(dirname(symlinkPath), skillSourceDir);
 
   try {
-    if (existsSync(symlinkPath)) {
-      const stats = lstatSync(symlinkPath);
-      if (!stats.isSymbolicLink()) return `${symlinkPath} exists and is not a symlink`;
-      if (readlinkSync(symlinkPath) === targetPath) return true;
-      unlinkSync(symlinkPath);
+    const stats = getPathStats(symlinkPath);
+    if (stats) {
+      if (stats.isSymbolicLink()) {
+        if (readlinkSync(symlinkPath) === targetPath) return true;
+        unlinkSync(symlinkPath);
+      } else {
+        rmSync(symlinkPath, { recursive: true, force: true });
+      }
     }
 
     mkdirSync(dirname(symlinkPath), { recursive: true });
diff --git a/apps/cli/tests/add-skill.test.ts b/apps/cli/tests/add-skill.test.ts
index db25f2311..0fcb521f8 100644
--- a/apps/cli/tests/add-skill.test.ts
+++ b/apps/cli/tests/add-skill.test.ts
@@ -1,8 +1,18 @@
-import { mkdtempSync, readFileSync, readdirSync, rmSync } from "node:fs";
+import {
+  lstatSync,
+  mkdirSync,
+  mkdtempSync,
+  readFileSync,
+  readdirSync,
+  readlinkSync,
+  rmSync,
+  symlinkSync,
+  writeFileSync,
+} from "node:fs";
 import { join } from "node:path";
 import { tmpdir } from "node:os";
 import { describe, expect, it, beforeEach, afterEach } from "vite-plus/test";
-import { extractTarEntries, readNullTerminated } from "../src/commands/add-skill";
+import { ensureAgentSymlink, extractTarEntries, readNullTerminated } from "../src/commands/add-skill";
 
 const TAR_HEADER_SIZE = 512;
 
@@ -108,3 +118,43 @@ describe("extractTarEntries", () => {
     expect(readdirSync(destDir)).toEqual([]);
   });
 });
+
+describe("ensureAgentSymlink", () => {
+  it("replaces an existing non-symlink expect directory with a symlink", () => {
+    const projectRoot = mkdtempSync(join(tmpdir(), "ensure-symlink-"));
+
+    try {
+      mkdirSync(join(projectRoot, ".agents", "skills", "expect"), { recursive: true });
+      mkdirSync(join(projectRoot, ".codex", "skills", "expect"), { recursive: true });
+      writeFileSync(join(projectRoot, ".codex", "skills", "expect", "old-file.txt"), "legacy");
+
+      const result = ensureAgentSymlink(projectRoot, "codex");
+
+      expect(result).toBe(true);
+      const linkedPath = join(projectRoot, ".codex", "skills", "expect");
+      expect(lstatSync(linkedPath).isSymbolicLink()).toBe(true);
+      expect(readlinkSync(linkedPath)).toBe("../../.agents/skills/expect");
+    } finally {
+      rmSync(projectRoot, { recursive: true, force: true });
+    }
+  });
+
+  it("replaces a broken symlink expect path with a valid symlink", () => {
+    const projectRoot = mkdtempSync(join(tmpdir(), "ensure-symlink-broken-"));
+
+    try {
+      mkdirSync(join(projectRoot, ".agents", "skills", "expect"), { recursive: true });
+      mkdirSync(join(projectRoot, ".codex", "skills"), { recursive: true });
+      symlinkSync("../../../.agents/skills/does-not-exist", join(projectRoot, ".codex", "skills", "expect"));
+
+      const result = ensureAgentSymlink(projectRoot, "codex");
+
+      expect(result).toBe(true);
+      const linkedPath = join(projectRoot, ".codex", "skills", "expect");
+      expect(lstatSync(linkedPath).isSymbolicLink()).toBe(true);
+      expect(readlinkSync(linkedPath)).toBe("../../.agents/skills/expect");
+    } finally {
+      rmSync(projectRoot, { recursive: true, force: true });
+    }
+  });
+});