diff --git a/scripts/lib/install/apply.js b/scripts/lib/install/apply.js
index 0ce44fae0..7da51910c 100644
--- a/scripts/lib/install/apply.js
+++ b/scripts/lib/install/apply.js
@@ -96,13 +96,22 @@ function readInstalledFileNoFollow(plan, operation) {
   }
 
   try {
+    const openedStat = fs.fstatSync(descriptor, { bigint: true });
+    const finalPathStat = fs.lstatSync(operation.destinationPath, { bigint: true });
+    if (finalPathStat.isSymbolicLink() || !finalPathStat.isFile()) {
+      return null;
+    }
+    const identityMatches = openedStat.ino === finalPathStat.ino
+      && (!openedStat.dev || !finalPathStat.dev || openedStat.dev === finalPathStat.dev);
+    if (!openedStat.isFile() || !identityMatches) {
+      throw new Error(
+        `Refusing to hash changed install destination: ${operation.destinationPath}`
+      );
+    }
     // Revalidate the full path after opening. The descriptor pins the file so
     // the digest and metadata refer to the same object.
     assertSafeInstallOperation(plan, operation);
     assertSafeClaudeSkillOperation(plan, operation);
-    if (!fs.fstatSync(descriptor).isFile()) {
-      return null;
-    }
     return fs.readFileSync(descriptor);
   } finally {
     fs.closeSync(descriptor);
@@ -457,7 +466,10 @@ function applyInstallPlan(plan, dependencies = {}) {
           stateWithContentDigests(migration.bridgeState, appliedPlan)
         );
       } catch (checkpointError) {
-        error.message += ` Install-state checkpoint also failed: ${checkpointError.message}`;
+        throw new Error(
+          `${error.message} Install-state checkpoint also failed: ${checkpointError.message}`,
+          { cause: error }
+        );
       }
     }
     throw error;
diff --git a/tests/lib/install-lifecycle.test.js b/tests/lib/install-lifecycle.test.js
index 8f72ebc66..7ddd8d48f 100644
--- a/tests/lib/install-lifecycle.test.js
+++ b/tests/lib/install-lifecycle.test.js
@@ -188,7 +188,16 @@ function managedOperation(kind, destinationPath, overrides = {}) {
         destinationPath,
         fs.constants.O_RDONLY | (fs.constants.O_NOFOLLOW || 0)
       );
-      if (fs.fstatSync(descriptor).isFile()) {
+      const openedStat = fs.fstatSync(descriptor, { bigint: true });
+      const finalPathStat = fs.lstatSync(destinationPath, { bigint: true });
+      const identityMatches = openedStat.ino === finalPathStat.ino
+        && (!openedStat.dev || !finalPathStat.dev || openedStat.dev === finalPathStat.dev);
+      if (
+        openedStat.isFile()
+        && finalPathStat.isFile()
+        && !finalPathStat.isSymbolicLink()
+        && identityMatches
+      ) {
         operation.contentSha256 = crypto.createHash('sha256')
           .update(fs.readFileSync(descriptor))
           .digest('hex');
@@ -212,6 +221,25 @@ function runTests() {
   let passed = 0;
   let failed = 0;
 
+  if (test('managed-operation digest never follows a final symlink', () => {
+    const tempDir = createTempDir('install-lifecycle-symlink-digest-');
+    const victimPath = path.join(tempDir, 'victim.md');
+    const symlinkPath = path.join(tempDir, 'managed.md');
+    try {
+      fs.writeFileSync(victimPath, 'user content\n');
+      try {
+        fs.symlinkSync(victimPath, symlinkPath, 'file');
+      } catch {
+        console.log('    (file symlink unsupported on this platform; skipping)');
+        return;
+      }
+      const operation = managedOperation('copy-file', symlinkPath);
+      assert.strictEqual(operation.contentSha256, undefined);
+    } finally {
+      cleanup(tempDir);
+    }
+  })) passed++; else failed++;
+
   if (test('normalizes default targets and dedupes adapter aliases', () => {
     const defaultTargets = normalizeTargets();