diff --git a/roles/pfsense_upgrade/tasks/upgrade.yml b/roles/pfsense_upgrade/tasks/upgrade.yml
index 834d7a1..8a8dbfb 100644
--- a/roles/pfsense_upgrade/tasks/upgrade.yml
+++ b/roles/pfsense_upgrade/tasks/upgrade.yml
@@ -128,20 +128,36 @@
 - name: Initiate system reboot
   ansible.builtin.raw: |
     /sbin/reboot
+  ignore_unreachable: true
+  ignore_errors: true
   when: 
     - perform_upgrade | bool
-    - upgrade_successful
+    - upgrade_successful | bool
     - _reboot_check.stdout | trim == "REBOOT_NEEDED"
 
-- name: Wait for system to come back online after reboot
-  ansible.builtin.wait_for_connection:
-    timeout: "{{ reboot_timeout | default(300) }}"
-    delay: 15
+# - name: Wait for system to come back online after reboot
+#   ansible.builtin.wait_for_connection:
+#     timeout: "{{ reboot_timeout | default(600) }}"
+#     delay: 15
+#   when: 
+#     - perform_upgrade | bool
+#     - upgrade_successful | bool
+#     - _reboot_check.stdout | trim == "REBOOT_NEEDED"
+
+- name: Wait for system to come back online (raw ping loop)
+  ansible.builtin.raw: |
+    for i in 1 2 3 4 5 6 7 8 9 10 11 12; do
+      sleep 10
+      /sbin/ping -c 1 -t 2 8.8.8.8 > /dev/null 2>&1 && exit 0
+    done
+    exit 1
+  register: _wait_result
+  ignore_errors: true
   when: 
     - perform_upgrade | bool
-    - upgrade_successful
+    - upgrade_successful | bool
     - _reboot_check.stdout | trim == "REBOOT_NEEDED"
-
+    
 # ---------------------------------------------------------------------------
 # 5. Final status and failure handling
 # ---------------------------------------------------------------------------