diff --git a/roles/kubernetes-apps/helm/tasks/main.yml b/roles/kubernetes-apps/helm/tasks/main.yml
index 5a89fb69c..0ac7edca9 100644
--- a/roles/kubernetes-apps/helm/tasks/main.yml
+++ b/roles/kubernetes-apps/helm/tasks/main.yml
@@ -17,6 +17,11 @@
   package:
     name: "{{ pyyaml_package }}"
     state: present
+  when: pyyaml_package is defined
+
+- name: Helm | Install PyYaml [flatcar]
+  include_tasks: pyyaml-flatcar.yml
+  when: ansible_os_family in ["Flatcar", "Flatcar Container Linux by Kinvolk"]
 
 - name: Helm | Download helm
   include_tasks: "../../../download/tasks/download_file.yml"
diff --git a/roles/kubernetes-apps/helm/tasks/pyyaml-flatcar.yml b/roles/kubernetes-apps/helm/tasks/pyyaml-flatcar.yml
new file mode 100644
index 000000000..ea0d63a08
--- /dev/null
+++ b/roles/kubernetes-apps/helm/tasks/pyyaml-flatcar.yml
@@ -0,0 +1,22 @@
+---
+- name: Get installed pip version
+  command: "{{ ansible_python_interpreter if ansible_python_interpreter is defined else 'python' }} -m pip --version"
+  register: pip_version_output
+  ignore_errors: yes
+  changed_when: false
+
+- name: Get installed PyYAML version
+  command: "{{ ansible_python_interpreter if ansible_python_interpreter is defined else 'python' }} -m pip show PyYAML"
+  register: pyyaml_version_output
+  ignore_errors: yes
+  changed_when: false
+
+- name: Install pip
+  command: "{{ ansible_python_interpreter if ansible_python_interpreter is defined else 'python' }} -m ensurepip --upgrade"
+  when: (pyyaml_version_output is failed) and (pip_version_output is failed)
+
+- name: Install PyYAML
+  ansible.builtin.pip:
+    name:
+      - PyYAML
+  when: (pyyaml_version_output is failed)