diff --git a/roles/common/defaults/main.yml b/roles/common/defaults/main.yml
index 11e746f1b1b0033f8b4ff22c57d3e477f1f6ef6c..a13792dab9b7d216427e296eced01dcc515cd924 100644
--- a/roles/common/defaults/main.yml
+++ b/roles/common/defaults/main.yml
@@ -12,6 +12,11 @@ prompt_id: null
 extra_backup_patterns:
   - "/root"
   - "/home"
+pip_check_requirements:
+  - click==6.7
+  - first==2.0.1
+  - pip-tools==1.9.0
+  - six==1.10.0
 
 # Internal use only.
 prompt_colour_mapping:
diff --git a/roles/common/files/pip_check_requirements_upgrades.sh b/roles/common/files/pip_check_requirements_upgrades.sh
new file mode 100755
index 0000000000000000000000000000000000000000..9d721287bebd8400ec0b811d2f31ee871a399b81
--- /dev/null
+++ b/roles/common/files/pip_check_requirements_upgrades.sh
@@ -0,0 +1,269 @@
+#!/bin/bash
+#
+# pip_check_requirements_upgrades.sh
+#
+# Copyright (C) 2017, Branko Majic <branko@majic.rs>
+#
+# This program is free software: you can redistribute it and/or modify
+# it under the terms of the GNU General Public License as published by
+# the Free Software Foundation, either version 3 of the License, or
+# (at your option) any later version.
+#
+# This program is distributed in the hope that it will be useful,
+# but WITHOUT ANY WARRANTY; without even the implied warranty of
+# MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the
+# GNU General Public License for more details.
+#
+# You should have received a copy of the GNU General Public License
+# along with this program.  If not, see <http://www.gnu.org/licenses/>.
+#
+
+program="pip_check_requirements_upgrades.sh"
+
+function usage() {
+    cat <<EOF
+$program, a non-interactive utility for checking for available upgrades in
+Python pip requirements files based on pip-tools
+
+Usage: $program [OPTIONS] configuration_directory
+
+$program a non-interactive utility for checking for available upgrades in Python
+pip requirements files based on pip-tools. Utility is written specifically with
+pip-tools in mind, and pip-tools must be available when running the utility.
+
+If you are unfamiliar with pip-tools, please read its documentation first, and
+make sure you fully understand how it works.
+
+Utility accepts a single positionl argument - path to configuration
+directory. Configuration directory should contain one or more sub-directories
+where each sub-directory is treated as describing a separate Python virtual
+environment. This allows the checks to be run for multiple virtual environments
+in a modular manner.
+
+Each sub-directory should contain one or more .in files with corresponding .txt
+file. Base names must match (i.e. if you have production.in, the requirements
+file must be called production.txt).
+
+Utility iterates over each .in/.txt pair, calculates new requirements based on
+the .in file, and diffs this against existing .txt file.
+
+Utility creates copy of existing requirements file, stripping it from all
+comments, then calculates new requirements file (storing result in temporary
+location as well), and runs a diff between them.
+
+If newer pacakges are available that would satisfiy the provided .in file, a
+diff is shown on standard output in addition to a warning message.
+
+$program accepts the following options:
+
+    -V virtualenv
+        Path to virtual environment with pre-installed pip-tools. If specified,
+        the virtual environment will be activated prior to running the utility.
+
+    -q
+        Quiet mode. Output a message only if newer packages are available.
+    -d
+        Enable debug mode.
+    -v
+        Show script licensing information.
+    -h
+        Show usage help.
+
+
+Please report bugs and send feature requests to <branko@majic.rs>.
+EOF
+}
+
+function version() {
+    cat <<EOF
+$program
+
++-----------------------------------------------------------------------+
+| Copyright (C) 2017, Branko Majic <branko@majic.rs>                    |
+|                                                                       |
+| This program is free software: you can redistribute it and/or modify  |
+| it under the terms of the GNU General Public License as published by  |
+| the Free Software Foundation, either version 3 of the License, or     |
+| (at your option) any later version.                                   |
+|                                                                       |
+| This program is distributed in the hope that it will be useful,       |
+| but WITHOUT ANY WARRANTY; without even the implied warranty of        |
+| MERCHANTABILITY or FITNESS FOR A PARTICULAR PURPOSE.  See the         |
+| GNU General Public License for more details.                          |
+|                                                                       |
+| You should have received a copy of the GNU General Public License     |
+| along with this program.  If not, see <http://www.gnu.org/licenses/>. |
++-----------------------------------------------------------------------+
+
+EOF
+}
+
+# Set-up colours for message printing if we're not piping and terminal is
+# capable of outputting the colors.
+_color_terminal=$(tput colors 2>&1)
+if [[ -t 1 ]] && (( ${_color_terminal} > 0 )); then
+    _text_bold=$(tput bold)
+    _text_white=$(tput setaf 7)
+    _text_blue=$(tput setaf 6)
+    _text_green=$(tput setaf 2)
+    _text_yellow=$(tput setaf 3)
+    _text_red=$(tput setaf 1)
+    _text_reset=$(tput sgr0)
+else
+    _text_bold=""
+    _text_white=""
+    _text_blue=""
+    _text_green=""
+    _text_yellow=""
+    _text_red=""
+    _text_reset=""
+fi
+
+# Set-up functions for printing coloured messages.
+function debug() {
+    if [[ $debug != 0 ]]; then
+        echo "${_text_bold}${_text_blue}[DEBUG]${_text_reset}" "$@"
+    fi
+}
+
+function info() {
+    echo "${_text_bold}${_text_white}[INFO] ${_text_reset}" "$@"
+}
+
+function success() {
+    echo "${_text_bold}${_text_green}[OK]   ${_text_reset}" "$@"
+}
+
+function warning() {
+    echo "${_text_bold}${_text_yellow}[WARN] ${_text_reset}" "$@"
+}
+
+function error() {
+    echo "${_text_bold}${_text_red}[ERROR]${_text_reset}" "$@" >&2
+}
+
+# Clean-up command for temporary files.
+function on_exit() {
+    debug "Cleaning-up temporary file: $tmp_current"
+    [[ -f $tmp_current ]] && rm "$tmp_current"
+
+    debug "Cleaning-up temporayr file: $tmp_new"
+    [[ -f $tmp_new ]] && rm "$tmp_new"
+}
+trap on_exit EXIT
+
+# Define error codes.
+SUCCESS=0
+ERROR_ARGUMENTS=1
+ERROR_CONFIG_DIR=2
+ERROR_PIP_TOOLS_MISSING=3
+
+# Disable debug and quiet modes by default.
+debug=0
+quiet=0
+
+# Set-up defaults.
+virtualenv=""
+
+# If no arguments were given, just show usage help.
+if [[ -z $1 ]]; then
+    usage
+    exit "$SUCCESS"
+fi
+
+# Parse the arguments
+while getopts "V:qdvh" opt; do
+    case "$opt" in
+	V) virtualenv="$OPTARG";;
+	q) quiet=1;;
+	d) debug=1;;
+        v) version
+           exit "$SUCCESS";;
+        h) usage
+           exit "$SUCCESS";;
+        *) usage
+           exit "$ERROR_ARGUMENTS";;
+    esac
+done
+i=$OPTIND
+shift $(($i-1))
+
+
+if [[ ${#@} == 0 ]]; then
+    error "Must pass configuration directory."
+    usage
+    exit "$ERROR_ARGUMENTS"
+fi
+
+# Verfiy positional arguments.
+config_dir="$1"
+if [[ ! -d $config_dir ]]; then
+    error "No such directory: $config_dir"
+    exit "$ERROR_ARGUMENTS"
+fi
+
+# Make sure virtual environment exists.
+if [[ -n $virtualenv && ! -f $virtualenv/bin/activate ]]; then
+    error "Invalid virtual environment specified: $virtualenv"
+    exit "$ERROR_ARGUMENTS"
+fi
+
+# Activate the virtual environment if it was specified.
+[[ -n $virtualenv ]] && source "$virtualenv/bin/activate"
+
+# Verify pip-compile is available.
+if ! which pip-compile >/dev/null 2>&1; then
+    error "Could not find command pip-compile from packagep pip-tools. Package might not be available in the virtual environment."
+    exit "$ERROR_PIP_TOOLS_MISSING"
+fi
+
+# Create temporary files where files where "normalised" outputs will be
+# stored.
+tmp_current=$(mktemp)
+tmp_new=$(mktemp)
+
+# Process each environment.
+for environment in "$config_dir"/*; do
+    # Empty directory.
+    if [[ ! -e $environment ]]; then
+	error "Configuration directory is empty: $config_dir"
+	exit "$ERROR_CONFIG_DIR"
+    fi
+
+    # Process each .in file.
+    for req_in in "$environment"/*.in; do
+	# Directory without .in files.
+	if [[ ! -e $req_in ]]; then
+	    error "No .in files in directory, skipping: $environment"
+	    continue
+	fi
+
+	# Figure out if .txt file exists.
+	req_txt="${req_in%.in}.txt"
+	if [[ ! -f $req_txt ]]; then
+	    warning "Missing .txt file for: $req_in"
+	    continue
+	fi
+
+	# Deploy the existing requirements file and the new one.
+	sed -e 's/[[:blank:]]*#.*//' "$req_txt" | grep -v "^$" | sort -u > "$tmp_current" 
+	if ! pip-compile --no-header --no-annotate --no-index --output-file "$tmp_new" "$req_in" > /dev/null; then
+	    error "Failed while running pip-compile command against (see error stack trace above): $req_in"
+	    continue
+	fi
+
+	# Run diff, storing the output and result.
+	diff=$(diff -u "$tmp_current" "$tmp_new")
+	result="$?"
+
+	# Show warning about available updates.
+	if [[ $result == 0 ]]; then
+	    [[ $quiet == 0 ]] && info "No upgrades available for: $req_txt"
+	else
+	    warning "Upgrades available for: $req_txt"
+	    echo
+	    echo "$diff"
+	    echo
+	fi
+    done
+done
diff --git a/roles/common/files/pipreqcheck_requirements.in b/roles/common/files/pipreqcheck_requirements.in
new file mode 100644
index 0000000000000000000000000000000000000000..2c362e602b6b13e495e9b08fc2afbc41b9e9fc84
--- /dev/null
+++ b/roles/common/files/pipreqcheck_requirements.in
@@ -0,0 +1 @@
+pip-tools
\ No newline at end of file
diff --git a/roles/common/tasks/main.yml b/roles/common/tasks/main.yml
index 17ca82f4befb2cdf6cda16dab31403394e035e26..84802926801cb72f1d7811151ec952855d0722b7 100644
--- a/roles/common/tasks/main.yml
+++ b/roles/common/tasks/main.yml
@@ -149,6 +149,65 @@
 - name: Install apticron (for checking available upgrades)
   apt: name=apticron state=installed
 
+# Implementation for checking pip requirements files via via pip-tools.
+- name: Install virtualenv for pip requirements checks
+  apt: name=virtualenv state=installed
+
+- name: Create dedicated group for user running pip requirements checks
+  group: name="pipreqcheck" gid="{{ pipreqcheck_gid | default(omit) }}" state=present
+
+- name: Create user for running pip requirements checks
+  user: name="pipreqcheck" uid="{{ pipreqcheck_uid | default(omit) }}" group="pipreqcheck"
+        home="/var/lib/pipreqcheck" state=present
+
+- name: Create directory for Python virtual environment used for installing/running pip-tools
+  file: path="/var/lib/pipreqcheck/virtualenv" state=directory
+        owner="pipreqcheck" group="pipreqcheck" mode="0750"
+
+- name: Create Python virtual environment used for installing/running pip-tools
+  become_user: "pipreqcheck"
+  command: /usr/bin/virtualenv --prompt "(pipreqcheck)" "/var/lib/pipreqcheck/virtualenv" creates="/var/lib/pipreqcheck/virtualenv/bin/activate"
+
+- name: Create directory for storing pip requirements files
+  file: path="/etc/pip_check_requirements_upgrades" state="directory"
+        owner="root" group="pipreqcheck" mode=750
+
+- name: Set-up directory for storing pip requirements file for pip-tools virtual environment itself
+  file: path="/etc/pip_check_requirements_upgrades/pipreqcheck" state="directory"
+        owner="root" group="pipreqcheck" mode=750
+
+- 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"
+        owner="root" group="pipreqcheck" mode=640
+
+- name: Deploy requirements file for pipreqcheck virtual environment
+  template: src="pipreqcheck_requirements.txt.j2" dest="/etc/pip_check_requirements_upgrades/pipreqcheck/requirements.txt"
+            owner="root" group="pipreqcheck" mode=640
+
+- name: Install latest pip in pip-tools virtual environment
+  become_user: "pipreqcheck"
+  pip: name=pip state=latest virtualenv="~pipreqcheck/virtualenv"
+
+- name: Install pip-tools if not present
+  become_user: "pipreqcheck"
+  pip: name=pip-tools state=present virtualenv="~pipreqcheck/virtualenv"
+
+- name: Synchronise pip-tools virtual environment via deployed requirements file
+  become_user: "pipreqcheck"
+  shell: "source ~pipreqcheck/virtualenv/bin/activate && pip-sync /etc/pip_check_requirements_upgrades/pipreqcheck/requirements.txt"
+  args:
+    executable: /bin/bash
+  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" dest="/usr/local/bin/pip_check_requirements_upgrades.sh"
+        owner=root group=root mode=755
+
+- name: Deploy crontab entry for checking pip requirements
+  cron: name="check_pip_requirements" cron_file="check_pip_requirements" hour=0 minute=0 job="/usr/local/bin/pip_check_requirements_upgrades.sh /etc/pip_check_requirements_upgrades"
+        state=present user=pipreqcheck
+
 - name: Explicitly run all handlers
   include: ../handlers/main.yml
   when: "handlers | default(False) | bool() == True"
diff --git a/roles/common/templates/pipreqcheck_requirements.txt.j2 b/roles/common/templates/pipreqcheck_requirements.txt.j2
new file mode 100644
index 0000000000000000000000000000000000000000..3ab42c6c01ed9b5480eaa48384498c5121d4e921
--- /dev/null
+++ b/roles/common/templates/pipreqcheck_requirements.txt.j2
@@ -0,0 +1,3 @@
+{% for requirement in pip_check_requirements %}
+{{ requirement }}
+{% endfor %}