diff --git a/tasks/plus/install-pip2.yml b/tasks/plus/install-pip2.yml
new file mode 100644
index 000000000..3a67bd372
--- /dev/null
+++ b/tasks/plus/install-pip2.yml
@@ -0,0 +1,19 @@
+- name: (Python 2) Get version 2.7 'pip' script
+  ansible.builtin.get_url:
+    url: "https://bootstrap.pypa.io/pip/2.7/get-pip.py"
+    dest: "/tmp/get-pip.py"
+    mode: "0755"
+
+- name: (Python 2) Check if 'pip' binary exists
+  ansible.builtin.stat:
+    path: /usr/bin/pip
+  ignore_errors: true
+  register: pip
+
+- name: (Python 2) Install 'pip' version 2.7
+  ansible.builtin.command: "python get-pip.py"
+  args:
+    chdir: /tmp/
+  when: not pip.stat.exists
+  register: pip_install
+  changed_when: pip_install.changed
diff --git a/tasks/plus/install-pip3.yml b/tasks/plus/install-pip3.yml
new file mode 100644
index 000000000..dc325aeca
--- /dev/null
+++ b/tasks/plus/install-pip3.yml
@@ -0,0 +1,7 @@
+- name: (Python 3) Install 'pip' package
+  ansible.builtin.package:
+    name: python3-pip
+
+- name: (Python 3) Ensure 'pip' is updated
+  ansible.builtin.pip:
+    name: pip>=21.2.4
diff --git a/tasks/plus/setup-license.yml b/tasks/plus/setup-license.yml
index 4f6b188cb..1689e9b58 100644
--- a/tasks/plus/setup-license.yml
+++ b/tasks/plus/setup-license.yml
@@ -47,6 +47,9 @@
 - name: (Debian/Red Hat/SLES OSs) Set up NGINX Plus license
   when: ansible_facts['os_family'] != 'Alpine'
   block:
+    - name: (RedHat) Install pip
+      ansible.builtin.include_tasks: "{{ role_path }}/tasks/plus/install-pip{{ ansible_python['version']['major'] }}.yml"
+
     - name: (Debian/Red Hat/SLES OSs) Create SSL directory
       ansible.builtin.file:
         path: /etc/ssl/nginx
@@ -64,8 +67,8 @@
         - "{{ nginx_license['key'] }}"
 
     - name: (Debian/Red Hat/SLES OSs) Install cryptography package
-      ansible.builtin.package:
-        name: "{{ (ansible_python['version']['major'] == 3) | ternary('python3-cryptography', 'python2-cryptography') }}"
+      ansible.builtin.pip:
+        name: cryptography
       when: not (ansible_facts['distribution'] == "OracleLinux" and ansible_facts['distribution_major_version'] == "8")
 
     - name: (OracleLinux 8) Install cryptography package