diff --git a/scripts/deploy.sh b/scripts/deploy.sh
index 16e01fe..5835277 100755
--- a/scripts/deploy.sh
+++ b/scripts/deploy.sh
@@ -159,14 +159,23 @@ if [ '${COMPOSE_UP[$TARGET]}' = '1' ]; then
   # A Caddyfile render is a bind-mount content change, not a container
   # config change: the caddy container often survives 'up -d' and keeps
   # serving its in-memory config. Reload explicitly; the file watcher
-  # (admin on) is the backstop if the API is not up yet.
+  # (admin on) is the backstop if the API is not up yet. If the reload
+  # cannot be applied at all (e.g. the running config has the admin API
+  # disabled -- the fix cannot ride the API it is meant to enable),
+  # restart the container so it reads the file on start.
+  caddy_reloaded=0
   for i in 1 2 3 4 5; do
     if podman exec caddy caddy reload --config /etc/caddy/Caddyfile --adapter caddyfile >/dev/null 2>&1; then
+      caddy_reloaded=1
       echo \"  Caddy reloaded.\"
       break
     fi
     sleep 3
   done
+  if [ \"\$caddy_reloaded\" -ne 1 ]; then
+    echo \"  Caddy reload failed; restarting the container to load the file.\"
+    podman restart caddy
+  fi
 else
   echo '[4/4] Skipping compose restart (stack runs as bare containers on this host)'
 fi
diff --git a/tests/deployment_flow.bats b/tests/deployment_flow.bats
index 99614a5..96742d5 100644
--- a/tests/deployment_flow.bats
+++ b/tests/deployment_flow.bats
@@ -45,6 +45,14 @@ load helpers
     grep -q 'caddy reload' "$REPO_ROOT/scripts/deploy.sh"
 }
 
+@test "deploy.sh restarts caddy when the reload cannot be applied" {
+    # If the running config has the admin API disabled (or the API is down),
+    # 'caddy reload' can never apply the new file -- the fix cannot be
+    # delivered over the API it is meant to enable. The fallback is a
+    # container restart, which always reads the file.
+    grep -q 'podman restart caddy' "$REPO_ROOT/scripts/deploy.sh"
+}
+
 @test "deploy.sh Caddyfile render survives a slash-bearing bcrypt hash" {
     local hash='$2a$14$dndiQ9EaycJv0w3Gp2oAYO/xH6O9x2ZRhMLJdCxrgi9rMn1te9D/spy'
     local rendered