diff --git a/api/caddy_manager.py b/api/caddy_manager.py
index dcb6154..3971feb 100644
--- a/api/caddy_manager.py
+++ b/api/caddy_manager.py
@@ -649,11 +649,12 @@ class CaddyManager(BaseServiceManager):
     # ── Active cert management ────────────────────────────────────────────
 
     def renew_cert(self) -> Dict[str, Any]:
-        """Trigger ACME cert renewal by reloading Caddy.
+        """Regenerate the Caddyfile, reload Caddy, and trigger ACME cert renewal.
 
-        Returns immediately with status='pending' so the caller can poll
-        GET /api/caddy/cert-status to track progress.  Not applicable to
-        LAN mode — callers should use upload_custom_cert() instead.
+        Regenerates first so a stale or broken on-disk Caddyfile never blocks
+        the reload.  Returns immediately with status='pending'; the caller
+        polls GET /api/caddy/cert-status to track progress.  Not applicable
+        to LAN mode — callers should use upload_custom_cert() instead.
         """
         ident = (self.config_manager.get_identity() if self.config_manager else {}) or {}
         domain_mode = ident.get('domain_mode', 'lan')
@@ -665,7 +666,17 @@ class CaddyManager(BaseServiceManager):
                          'Upload a custom certificate instead.',
             }
 
-        if not self.reload_caddy():
+        # Regenerate → write → reload in one shot so the Caddyfile is always fresh.
+        if self.config_manager:
+            try:
+                ok = self.regenerate_with_installed([])
+            except Exception as exc:
+                logger.error('renew_cert: regenerate_with_installed failed: %s', exc)
+                ok = False
+        else:
+            ok = self.reload_caddy()
+
+        if not ok:
             return {'ok': False, 'error': 'Caddy reload failed — check Caddy logs.'}
 
         # Invalidate the cached status so the next poll triggers a fresh SSL check.
diff --git a/tests/test_caddy_manager.py b/tests/test_caddy_manager.py
index 3708d0b..f85590f 100644
--- a/tests/test_caddy_manager.py
+++ b/tests/test_caddy_manager.py
@@ -493,17 +493,17 @@ class TestRenewCert(unittest.TestCase):
         self.assertFalse(result['ok'])
         self.assertIn('LAN', result['error'])
 
-    def test_acme_mode_calls_reload(self):
+    def test_acme_mode_calls_regenerate(self):
         mgr = _mgr(identity={'domain_mode': 'pic_ngo'})
-        with patch.object(mgr, 'reload_caddy', return_value=True) as mock_reload:
+        with patch.object(mgr, 'regenerate_with_installed', return_value=True) as mock_regen:
             result = mgr.renew_cert()
-        mock_reload.assert_called_once()
+        mock_regen.assert_called_once_with([])
         self.assertTrue(result['ok'])
         self.assertEqual(result['status'], 'pending')
 
     def test_reload_failure_propagated(self):
         mgr = _mgr(identity={'domain_mode': 'cloudflare'})
-        with patch.object(mgr, 'reload_caddy', return_value=False):
+        with patch.object(mgr, 'regenerate_with_installed', return_value=False):
             result = mgr.renew_cert()
         self.assertFalse(result['ok'])
         self.assertIn('reload failed', result['error'])
@@ -512,7 +512,7 @@ class TestRenewCert(unittest.TestCase):
         import time
         mgr = _mgr(identity={'domain_mode': 'pic_ngo'})
         mgr._cert_refreshed_at = time.monotonic()
-        with patch.object(mgr, 'reload_caddy', return_value=True):
+        with patch.object(mgr, 'regenerate_with_installed', return_value=True):
             mgr.renew_cert()
         self.assertIsNone(mgr._cert_refreshed_at)