diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.in b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.in
new file mode 100644
index 0000000000000000000000000000000000000000..68f017c3bbb61b0cb4f1adcaacab91c89326e036
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.in
@@ -0,0 +1 @@
+urllib3~=1.24.0
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.txt b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.txt
new file mode 100644
index 0000000000000000000000000000000000000000..5c118370aa97ff0863958d2373515789b78d76d0
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/with_updates/requirements.txt
@@ -0,0 +1,7 @@
+#
+# This file is autogenerated by pip-compile
+# To update, run:
+#
+#    pip-compile
+#
+urllib3==1.24.2           # via -r requirements.in
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.in b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.in
new file mode 100644
index 0000000000000000000000000000000000000000..68f017c3bbb61b0cb4f1adcaacab91c89326e036
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.in
@@ -0,0 +1 @@
+urllib3~=1.24.0
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.txt b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.txt
new file mode 100644
index 0000000000000000000000000000000000000000..0b886c8ea31924572b67de67a0c5a102450a5e0f
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades-py3/without_updates/requirements.txt
@@ -0,0 +1,7 @@
+#
+# This file is autogenerated by pip-compile
+# To update, run:
+#
+#    pip-compile
+#
+urllib3==1.24.3           # via -r requirements.in
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.in b/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.in
new file mode 100644
index 0000000000000000000000000000000000000000..68f017c3bbb61b0cb4f1adcaacab91c89326e036
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.in
@@ -0,0 +1 @@
+urllib3~=1.24.0
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.txt b/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.txt
new file mode 100644
index 0000000000000000000000000000000000000000..5c118370aa97ff0863958d2373515789b78d76d0
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades/with_updates/requirements.txt
@@ -0,0 +1,7 @@
+#
+# This file is autogenerated by pip-compile
+# To update, run:
+#
+#    pip-compile
+#
+urllib3==1.24.2           # via -r requirements.in
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.in b/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.in
new file mode 100644
index 0000000000000000000000000000000000000000..68f017c3bbb61b0cb4f1adcaacab91c89326e036
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.in
@@ -0,0 +1 @@
+urllib3~=1.24.0
diff --git a/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.txt b/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.txt
new file mode 100644
index 0000000000000000000000000000000000000000..0b886c8ea31924572b67de67a0c5a102450a5e0f
--- /dev/null
+++ b/roles/common/molecule/default/files/pip_check_requirements_upgrades/without_updates/requirements.txt
@@ -0,0 +1,7 @@
+#
+# This file is autogenerated by pip-compile
+# To update, run:
+#
+#    pip-compile
+#
+urllib3==1.24.3           # via -r requirements.in
diff --git a/roles/common/molecule/default/playbook.yml b/roles/common/molecule/default/playbook.yml
index b7c06c07f243a3e669cc078a3f3512242eb62564..43847a26c525b79ef53fd35f4038cc449513d3eb 100644
--- a/roles/common/molecule/default/playbook.yml
+++ b/roles/common/molecule/default/playbook.yml
@@ -13,3 +13,40 @@
   become: true
   roles:
     - common
+
+- hosts: parameters-mandatory,parameters-optional
+  become: true
+  tasks:
+
+    - name: Set-up directories for testing pip requirements upgrade checks script
+      file:
+        path: "{{ item }}"
+        state: directory
+        owner: root
+        group: pipreqcheck
+        mode: 0750
+      with_items:
+        - "/tmp/pip_check_requirements_upgrades"
+        - "/tmp/pip_check_requirements_upgrades/with_updates"
+        - "/tmp/pip_check_requirements_upgrades/without_updates"
+        - "/tmp/pip_check_requirements_upgrades-py3"
+        - "/tmp/pip_check_requirements_upgrades-py3/with_updates"
+        - "/tmp/pip_check_requirements_upgrades-py3/without_updates"
+
+    - name: Deploy files for testing pip requirements upgrade checks script
+      copy:
+        src: "{{ item }}"
+        dest: "/tmp/{{ item }}"
+        owner: root
+        group: pipreqcheck
+        mode: 0640
+        directory_mode: 0750
+      with_items:
+        - "pip_check_requirements_upgrades/with_updates/requirements.in"
+        - "pip_check_requirements_upgrades/with_updates/requirements.txt"
+        - "pip_check_requirements_upgrades/without_updates/requirements.in"
+        - "pip_check_requirements_upgrades/without_updates/requirements.txt"
+        - "pip_check_requirements_upgrades-py3/with_updates/requirements.in"
+        - "pip_check_requirements_upgrades-py3/with_updates/requirements.txt"
+        - "pip_check_requirements_upgrades-py3/without_updates/requirements.in"
+        - "pip_check_requirements_upgrades-py3/without_updates/requirements.txt"
diff --git a/roles/common/molecule/default/tests/test_default.py b/roles/common/molecule/default/tests/test_default.py
index f481064435a30e5e108a7b45684b6ad21140320b..89c6047e75faec911565c444d66e8dd89cd53884 100644
--- a/roles/common/molecule/default/tests/test_default.py
+++ b/roles/common/molecule/default/tests/test_default.py
@@ -1,4 +1,5 @@
 import os
+import re
 
 import testinfra.utils.ansible_runner
 
@@ -403,3 +404,30 @@ def test_pipreqcheck_virtualenv_wrong_python_version_not_present(host, wrong_pyt
         wrong_python_path_file = host.file(wrong_python_path)
 
         assert not wrong_python_path_file.exists
+
+
+@pytest.mark.parametrize('environment,config_directory', [
+    ('/var/lib/pipreqcheck/virtualenv', '/tmp/pip_check_requirements_upgrades'),
+    ('/var/lib/pipreqcheck/virtualenv-py3', '/tmp/pip_check_requirements_upgrades-py3'),
+])
+def test_pipreqcheck_script_output(host, environment, config_directory):
+    """
+    Tests if the pip_check_requirements_upgrades.sh script properly
+    reports available updates or not.
+    """
+
+    expected_line_count = 9
+    expected_warning_message = "[WARN]  Upgrades available for: %s/with_updates/requirements.txt" % config_directory
+    expected_package_diff = "@@ -1 +1 @@\n-urllib3==1.24.2\n+urllib3==1.24.3"
+
+    with host.sudo("pipreqcheck"):
+        report = host.run("/usr/local/bin/pip_check_requirements_upgrades.sh -q -V %s %s", environment, config_directory)
+
+        # Clean-up the SSH warning from the beginning of stderr if
+        # present.
+        stderr = re.sub("^Warning: Permanently added.*?\r\n", "", report.stderr)
+
+    assert stderr == ""
+    assert len(report.stdout.split("\n")) == expected_line_count
+    assert expected_warning_message in report.stdout
+    assert expected_package_diff in report.stdout