diff --git a/tests/test_security_guards.py b/tests/test_security_guards.py
index 47eacbc..7ec094e 100644
--- a/tests/test_security_guards.py
+++ b/tests/test_security_guards.py
@@ -125,6 +125,29 @@ class GitignoreGuardTests(GuardRepoFixture):
         self.assertEqual(result.returncode, 0, result.stdout + result.stderr)
 
 
+class GitignoreNegationTests(GuardRepoFixture):
+    def test_negation_reincluding_personal_data_fails(self):
+        # .gitignore is order-sensitive: `!salary_data.json` after the
+        # `salary_data.json` rule re-includes the file, so the required rule is
+        # still present but no longer takes effect. Set membership on the
+        # required rules cannot see this, so the negation must be rejected.
+        self.write_gitignore(list(security_guards.REQUIRED_IGNORE_RULES) + ["!salary_data.json"])
+        result = run_guards(self.root)
+        self.assertEqual(result.returncode, 1, result.stdout + result.stderr)
+        self.assertIn("negation rule not in the reviewed allowlist", result.stdout)
+        self.assertIn("!salary_data.json", result.stdout)
+
+    def test_allowlisted_negations_pass(self):
+        # The template's own benign negations (example CV/cover letter, fonts,
+        # .gitkeep placeholders) must keep passing.
+        self.write_gitignore(
+            list(security_guards.REQUIRED_IGNORE_RULES)
+            + sorted(security_guards.ALLOWED_IGNORE_NEGATIONS)
+        )
+        result = run_guards(self.root)
+        self.assertEqual(result.returncode, 0, result.stdout + result.stderr)
+
+
 class ManifestGuardTests(GuardRepoFixture):
     def test_each_lifecycle_script_fails(self):
         for script in sorted(security_guards.FORBIDDEN_SCRIPTS):
diff --git a/tools/security_guards.py b/tools/security_guards.py
index 4eb783f..e9102f6 100644
--- a/tools/security_guards.py
+++ b/tools/security_guards.py
@@ -13,9 +13,10 @@ Checks:
 1. .claude/settings.json — every permissions.allow entry must be in the exact
    allowlist below. Catches permission widening (e.g. Bash(*), Bash(curl:*)),
    which would auto-approve commands on every fork.
-2. .gitignore — the personal-data ignore rules must all still be present.
-   Catches weakening that would make future users silently commit their
-   tracker, profile exports, or application archives.
+2. .gitignore — the personal-data ignore rules must all still be present,
+   and no un-allowlisted negation (!pattern) may re-include them. Catches
+   weakening that would make future users silently commit their tracker,
+   profile exports, or application archives.
 3. .agents/**/package.json — no npm/bun lifecycle scripts (preinstall,
    install, postinstall, prepare, prepack) and no trustedDependencies.
    Catches code execution smuggled into `bun install`.
@@ -55,6 +56,20 @@ REQUIRED_IGNORE_RULES = [
     "job_search_tracker.csv",
 ]
 
+# Negation (re-include) rules the template legitimately ships. .gitignore is
+# order-sensitive: a later `!pattern` re-includes a path an earlier rule
+# excluded, so a rule can be physically present in REQUIRED_IGNORE_RULES yet
+# no longer ignored (e.g. adding `!salary_data.json`). Set membership on the
+# required rules cannot see that. Any negation outside this allowlist is a
+# failure - add an intentional one here in the same PR, exactly as with
+# ALLOWED_PERMISSIONS, so the widening is explicit and reviewable.
+ALLOWED_IGNORE_NEGATIONS = {
+    "!cover_letters/OpenFonts/fonts/**",
+    "!cv/main_example.tex",
+    "!cover_letters/cover_example.tex",
+    "!documents/**/.gitkeep",
+}
+
 FORBIDDEN_SCRIPTS = {"preinstall", "install", "postinstall", "prepare", "prepack"}
 
 
@@ -93,10 +108,11 @@ def check_permissions() -> None:
 def check_gitignore() -> None:
     path = ROOT / ".gitignore"
     try:
-        rules = {line.strip() for line in path.read_text(encoding="utf-8").splitlines()}
+        lines = [line.strip() for line in path.read_text(encoding="utf-8").splitlines()]
     except OSError as exc:
         errors.append(f".gitignore: unreadable: {exc}")
         return
+    rules = set(lines)
     for rule in REQUIRED_IGNORE_RULES:
         if rule not in rules:
             errors.append(
@@ -105,6 +121,15 @@ def check_gitignore() -> None:
                 "or was renamed intentionally, update REQUIRED_IGNORE_RULES in "
                 "tools/security_guards.py in the same PR."
             )
+    for line in lines:
+        if line.startswith("!") and line not in ALLOWED_IGNORE_NEGATIONS:
+            errors.append(
+                f".gitignore: negation rule not in the reviewed allowlist: {line!r}. "
+                "A negation re-includes a path an earlier rule excluded and can silently "
+                "re-expose personal data (a required ignore rule stays present but stops "
+                "taking effect). If this negation is intentional, add it to "
+                "ALLOWED_IGNORE_NEGATIONS in tools/security_guards.py in the same PR."
+            )
 
 
 def check_package_manifests() -> None: