diff --git a/tasks/get_system_key.yml b/tasks/get_system_key.yml
index 0ff606e..9778eea 100644
--- a/tasks/get_system_key.yml
+++ b/tasks/get_system_key.yml
@@ -3,6 +3,9 @@
   command:    grep -o -P '(?<=systemKey\":\")[a-zA-Z0-9]*' {{ jumpcloud_agent_config }}
   register:   jumpcloud_system_key_result
   become:     "{{ jumpcloud_use_sudo }}"
+  retries: 5
+  delay: 3
+  until: jumpcloud_system_key_result.rc == 0
   changed_when: "not jumpcloud_system_key_result.stdout"
 
 - name: Set Jumpcloud System Key