diff --git a/README.md b/README.md
index e86ce10..9c14260 100644
--- a/README.md
+++ b/README.md
@@ -50,5 +50,5 @@ pip3 install awscli
 pip3 install pipenv
 ```
 
-### If Yubico is installed, run this : 
-`sudo ansible-playbook ~/Code/dotfiles/mac_playbook.yaml`
+### If Yubico is installed, run this :
+`sudo ansible-playbook ~/Code/dotfiles/macsecure_playbook.yaml`
diff --git a/dot_scripts/ansible/mac_playbook.yaml b/dot_scripts/ansible/macsecure_playbook.yaml
similarity index 52%
rename from dot_scripts/ansible/mac_playbook.yaml
rename to dot_scripts/ansible/macsecure_playbook.yaml
index 54b32ad..0ab7d1a 100644
--- a/dot_scripts/ansible/mac_playbook.yaml
+++ b/dot_scripts/ansible/macsecure_playbook.yaml
@@ -3,7 +3,29 @@
   connection: local
   become_method: sudo
   become: yes
+
   tasks:
+   - name: Check yubikey binaries are installed
+     stat:
+       path: "{{ item }}"
+     with_items:
+      - /usr/local/bin/ykpamcfg
+      - "/Applications/YubiKey\ Manager.app/Contents/MacOS/ykman"
+
+   - name: Check Yubico is recognized
+     shell: "'/Applications/YubiKey Manager.app/Contents/MacOS/ykman' list | awk '{print $6}'"
+     register: yubicoChallenge
+     failed_when: "yubicoChallenge.rc != 0 or yubicoChallenge.stdout == ''"
+
+   - name: Get current user
+     become: false
+     local_action: command whoami
+     register: username_on_host
+
+   - name: Check yubico challenge exists
+     stat:
+       path: "/Users/{{ username_on_host.stdout }}/.yubico/challenge-{{ yubicoChallenge.stdout }}"
+
    - name: Ensure yubikey is needed for authentication at login screen
      lineinfile:
        path: "{{ item }}"