diff --git a/molecule/default/tests/test_default.py b/molecule/default/tests/test_default.py
index 4229110..a4f6def 100644
--- a/molecule/default/tests/test_default.py
+++ b/molecule/default/tests/test_default.py
@@ -15,8 +15,16 @@ def test_python_pip_packages_installed(host):
     assert apt_package_python3.is_installed
     assert apt_package_pip.is_installed
 
+def test_pip_installed_latest(host):
+    """Validate pip is installed and up-to-date"""
+    pip_packages_list = host.pip.get_packages(pip_path='pip')
+    pip_outdated_list = host.pip.get_outdated_packages(pip_path='pip')
+    assert 'pip' in pip_packages_list
+    assert 'pip' not in pip_outdated_list
+
 def test_packages_not_installed(host):
-    """Validate vim is installed"""
-    pip_packages_list = host.pip_package.get_packages(pip_path='pip')
-    print(pip_packages_list)
-    assert True == False
+    """Validate docker, yamllint and vault-cli are not installed"""
+    pip_packages_list = host.pip.get_packages(pip_path='pip')
+    assert 'docker' not in pip_packages_list
+    assert 'yamllint' not in pip_packages_list
+    assert 'vault-cli' not in pip_packages_list
diff --git a/molecule/with_custom_packages/tests/test_default.py b/molecule/with_custom_packages/tests/test_default.py
index 99cf339..66165b2 100644
--- a/molecule/with_custom_packages/tests/test_default.py
+++ b/molecule/with_custom_packages/tests/test_default.py
@@ -1,5 +1,6 @@
 """Role testing files using testinfra."""
-import json
+from packaging import version
+
 
 def test_hosts_file(host):
     """Validate /etc/hosts file."""
@@ -15,11 +16,22 @@ def test_python_pip_packages_installed(host):
     assert apt_package_python3.is_installed
     assert apt_package_pip.is_installed
 
-def test_packages_not_installed(host):
-    """Validate vim is installed"""
-    pip_packages_list = host.pip_package.get_packages(pip_path='pip')
-    assert pip_packages_list['pip']
-    assert pip_packages_list['docker']
-    assert pip_packages_list['zeubi']
-    print(pip_packages_list)
+def test_pip_installed_latest(host):
+    """Validate pip is installed and up-to-date"""
+    pip_packages_list = host.pip.get_packages(pip_path='pip')
+    pip_outdated_list = host.pip.get_outdated_packages(pip_path='pip')
+    assert 'pip' in pip_packages_list
+    assert 'pip' not in pip_outdated_list
 
+def test_packages_installed(host):
+    """Validate docker, yamllint and vault-cli are installed"""
+    pip_packages_list = host.pip.get_packages(pip_path='pip')
+    pip_outdated_list = host.pip.get_outdated_packages(pip_path='pip')
+    assert 'docker' in pip_packages_list
+    assert 'docker' not in  pip_outdated_list
+    assert 'yamllint' in pip_packages_list
+    assert 'yamllint' in  pip_outdated_list
+    assert version.parse(pip_packages_list['yamllint']['version']) == version.parse("1.24")
+    assert 'vault-cli' in pip_packages_list
+    assert 'vault-cli' in  pip_outdated_list
+    assert version.parse(pip_packages_list['vault-cli']['version']) < version.parse("3.1.0")
diff --git a/tasks/prerequisites.yml b/tasks/prerequisites.yml
index fac4de4..36ac285 100644
--- a/tasks/prerequisites.yml
+++ b/tasks/prerequisites.yml
@@ -11,3 +11,8 @@
       - name: "{{ manage_pip_packages_pip3_package_name }}"
         version: latest
         state: present
+
+- name: "Update pip to latest"
+  ansible.builtin.pip:
+    name: pip
+    extra_args: --upgrade