diff --git a/etc/kayobe/ansible/reboot.yml b/etc/kayobe/ansible/reboot.yml
index 8810afd7f..a6deb536c 100644
--- a/etc/kayobe/ansible/reboot.yml
+++ b/etc/kayobe/ansible/reboot.yml
@@ -4,7 +4,19 @@
   serial: "{{ lookup('env', 'ANSIBLE_SERIAL') | default(1, true) }}"
   tags:
     - reboot
+  vars:
+    reboot_timeout_s: "{{ 20 * 60 }}"
   tasks:
     - name: Reboot and wait
       become: true
       reboot:
+        reboot_timeout: "{{ reboot_timeout_s }}"
+        search_paths:
+          # Systems running molly-guard hang waiting for confirmation before rebooting without this.
+          - "/lib/molly-guard"
+          # Default list:
+          - "/sbin"
+          - "/bin"
+          - "/usr/sbin"
+          - "/usr/bin"
+          - "/usr/local/sbin"
diff --git a/etc/kayobe/ansible/ubuntu-upgrade.yml b/etc/kayobe/ansible/ubuntu-upgrade.yml
index 66ed49643..b7cfe7338 100644
--- a/etc/kayobe/ansible/ubuntu-upgrade.yml
+++ b/etc/kayobe/ansible/ubuntu-upgrade.yml
@@ -40,6 +40,15 @@
       reboot:
         reboot_timeout: "{{ reboot_timeout_s }}"
         connect_timeout: 600
+        search_paths:
+          # Systems running molly-guard hang waiting for confirmation before rebooting without this.
+          - "/lib/molly-guard"
+          # Default list:
+          - "/sbin"
+          - "/bin"
+          - "/usr/sbin"
+          - "/usr/bin"
+          - "/usr/local/sbin"
       become: true
       when: file_status.stat.exists
 
@@ -101,6 +110,15 @@
       reboot:
         reboot_timeout: "{{ reboot_timeout_s }}"
         connect_timeout: 600
+        search_paths:
+          # Systems running molly-guard hang waiting for confirmation before rebooting without this.
+          - "/lib/molly-guard"
+          # Default list:
+          - "/sbin"
+          - "/bin"
+          - "/usr/sbin"
+          - "/usr/bin"
+          - "/usr/local/sbin"
       become: true
 
     - name: Update distribution facts