diff --git a/playbooks/roles/insightvm_agent/tasks/main.yml b/playbooks/roles/insightvm_agent/tasks/main.yml
index 8179bf48801..3d798ac2327 100644
--- a/playbooks/roles/insightvm_agent/tasks/main.yml
+++ b/playbooks/roles/insightvm_agent/tasks/main.yml
@@ -10,6 +10,7 @@
   stat:
     path: /etc/systemd/system/ir_agent.service
   register: r7_service
+  retries: 3
   tags:
     - manage_rapid7_check_agent
 
diff --git a/playbooks/roles/security/tasks/security-amazon.yml b/playbooks/roles/security/tasks/security-amazon.yml
index 6085d38061e..1ef8d15e2db 100644
--- a/playbooks/roles/security/tasks/security-amazon.yml
+++ b/playbooks/roles/security/tasks/security-amazon.yml
@@ -30,6 +30,7 @@
 - name: "Take security updates during ansible runs"
   command: "{{ item }}"
   when: SECURITY_UPGRADE_ON_ANSIBLE
+  retries: 3
   with_items:
     - yum check-update --security
     - yum update --security -y
diff --git a/playbooks/roles/security/tasks/security-ubuntu.yml b/playbooks/roles/security/tasks/security-ubuntu.yml
index 8dc273dc902..ffaad59b3ce 100644
--- a/playbooks/roles/security/tasks/security-ubuntu.yml
+++ b/playbooks/roles/security/tasks/security-ubuntu.yml
@@ -24,6 +24,7 @@
 - name: Disable unattended-upgrades if Xenial (16.04)
   command: "{{ item }}"
   when: ansible_distribution_release == 'xenial' and not SECURITY_UNATTENDED_UPGRADES
+  retries: 3
   with_items:
     - "systemctl disable apt-daily.service"
     - "systemctl disable apt-daily.timer"