diff --git a/scripts/deploy-to-target.sh b/scripts/deploy-to-target.sh
index 3ce24086..6cc5c90a 100755
--- a/scripts/deploy-to-target.sh
+++ b/scripts/deploy-to-target.sh
@@ -624,6 +624,15 @@ if [ "$LIVE" = true ]; then
       scp $SSH_OPTS "$NGINX_CFG" "$TARGET_HOST:/tmp/nginx-archipelago.conf" 2>/dev/null || true
       ssh $SSH_OPTS "$TARGET_HOST" '
         sudo cp /tmp/nginx-archipelago.conf /etc/nginx/sites-available/archipelago
+        # Make sites-enabled a symlink to sites-available so future
+        # config updates actually take effect. Older deploys left
+        # sites-enabled as a regular file that fell out of sync.
+        if [ -f /etc/nginx/sites-enabled/archipelago ] && [ ! -L /etc/nginx/sites-enabled/archipelago ]; then
+            sudo rm -f /etc/nginx/sites-enabled/archipelago
+            sudo ln -s /etc/nginx/sites-available/archipelago /etc/nginx/sites-enabled/archipelago
+        elif [ ! -e /etc/nginx/sites-enabled/archipelago ]; then
+            sudo ln -s /etc/nginx/sites-available/archipelago /etc/nginx/sites-enabled/archipelago
+        fi
         rm -f /tmp/nginx-archipelago.conf
       ' 2>/dev/null || true
     fi