diff --git a/roles/common/tasks/main.yml b/roles/common/tasks/main.yml
index 861fff5b90e5597804ea76824bb52f35789d4b1b..65531e3ba4cc489a0b1d1aa0843415f3f6361aa6 100644
--- a/roles/common/tasks/main.yml
+++ b/roles/common/tasks/main.yml
@@ -298,18 +298,24 @@
 
 - name: Create directory for Python virtual environment used for installing/running pip-tools
   file:
-    path: "/var/lib/pipreqcheck/virtualenv"
+    path: "{{ item }}"
     state: directory
     owner: pipreqcheck
     group: pipreqcheck
     mode: 0750
+  with_items:
+    - "/var/lib/pipreqcheck/virtualenv"
+    - "/var/lib/pipreqcheck/virtualenv-py3"
 
 - name: Create Python virtual environment used for installing/running pip-tools
-  command: "/usr/bin/virtualenv --prompt '(pipreqcheck)' '/var/lib/pipreqcheck/virtualenv'"
+  command: "/usr/bin/virtualenv --prompt '({{ item.key }})' '{{ item.value }}'"
   args:
     creates: '/var/lib/pipreqcheck/virtualenv/bin/activate'
   become: true
   become_user: "pipreqcheck"
+  with_dict:
+    pipreqcheck: "/var/lib/pipreqcheck/virtualenv"
+    pipreqcheck-py3: "/var/lib/pipreqcheck/virtualenv-py3"
   tags:
     # [ANSIBLE0012] Commands should not change things if nothing needs doing
     #   Command will not run if the virtualenv has already been created,
@@ -318,53 +324,71 @@
 
 - name: Create directory for storing pip requirements files
   file:
-    path: "/etc/pip_check_requirements_upgrades"
+    path: "{{ item }}"
     state: "directory"
     owner: root
     group: pipreqcheck
     mode: 0750
+  with_items:
+    - "/etc/pip_check_requirements_upgrades"
+    - "/etc/pip_check_requirements_upgrades-py3"
 
 - name: Set-up directory for storing pip requirements file for pip-tools virtual environment itself
   file:
-    path: "/etc/pip_check_requirements_upgrades/pipreqcheck"
+    path: "{{ item }}"
     state: "directory"
     owner: root
     group: pipreqcheck
     mode: 0750
+  with_items:
+    - "/etc/pip_check_requirements_upgrades/pipreqcheck"
+    - "/etc/pip_check_requirements_upgrades-py3/pipreqcheck"
 
 - name: Deploy .in file for pip requirements in pip-tools virtual environment
   copy:
     src: "pipreqcheck_requirements.in"
-    dest: "/etc/pip_check_requirements_upgrades/pipreqcheck/requirements.in"
+    dest: "{{ item }}"
     owner: root
     group: pipreqcheck
     mode: 0640
+  with_items:
+    - "/etc/pip_check_requirements_upgrades/pipreqcheck/requirements.in"
+    - "/etc/pip_check_requirements_upgrades-py3/pipreqcheck/requirements.in"
 
 - name: Deploy requirements file for pipreqcheck virtual environment
   template:
     src: "pipreqcheck_requirements.txt.j2"
-    dest: "/etc/pip_check_requirements_upgrades/pipreqcheck/requirements.txt"
+    dest: "{{ item }}"
     owner: root
     group: pipreqcheck
     mode: 0640
+  with_items:
+    - "/etc/pip_check_requirements_upgrades/pipreqcheck/requirements.txt"
+    - "/etc/pip_check_requirements_upgrades-py3/pipreqcheck/requirements.txt"
 
 - name: Install latest pip in pip-tools virtual environment
   pip:
     name:
-      - "pip>=9.0.0,<10.0.0"
-    virtualenv: "~pipreqcheck/virtualenv"
+      - "pip>=18.0.0,<19.0.0"
+    virtualenv: "{{ item }}"
   become: true
   become_user: "pipreqcheck"
+  with_items:
+    - "~pipreqcheck/virtualenv"
+    - "~pipreqcheck/virtualenv-py3"
 
 - name: Install pip-tools if not present
   pip:
     name: pip-tools
     state: present
-    virtualenv: "~pipreqcheck/virtualenv"
+    virtualenv: "{{ item }}"
   become: true
   become_user: "pipreqcheck"
+  with_items:
+    - "~pipreqcheck/virtualenv"
+    - "~pipreqcheck/virtualenv-py3"
 
-- name: Synchronise pip-tools virtual environment via deployed requirements file
+- name: Synchronise pip-tools virtual environment via deployed requirements file (Python 2)
   shell: "source ~pipreqcheck/virtualenv/bin/activate && pip-sync /etc/pip_check_requirements_upgrades/pipreqcheck/requirements.txt"
   args:
     executable: /bin/bash
@@ -373,6 +397,15 @@
   register: pipreqcheck_pip_sync
   changed_when: "pipreqcheck_pip_sync.stdout != 'Everything up-to-date'"
 
+- name: Synchronise pip-tools virtual environment via deployed requirements file (Python 3)
+  shell: "source ~pipreqcheck/virtualenv-py3/bin/activate && pip-sync /etc/pip_check_requirements_upgrades-py3/pipreqcheck/requirements.txt"
+  args:
+    executable: /bin/bash
+  become: true
+  become_user: "pipreqcheck"
+  register: pipreqcheck_pip_sync
+  changed_when: "pipreqcheck_pip_sync.stdout != 'Everything up-to-date'"
+
 - name: Deploy script for checking available upgrades
   copy:
     src: "pip_check_requirements_upgrades.sh"
@@ -389,6 +422,14 @@
     group: root
     mode: 0644
 
+- name: Deploy crontab entry for checking pip requirements
+  copy:
+    src: "cron_check_pip_requirements-py3"
+    dest: "/etc/cron.d/check_pip_requirements-py3"
+    owner: root
+    group: root
+    mode: 0644
+
 - name: Install NTP packages
   apt:
     name: