diff --git a/Makefile b/Makefile
index 1e8fdb5e14..3755c20aa8 100644
--- a/Makefile
+++ b/Makefile
@@ -23,7 +23,7 @@ DEVEL_IMAGE_NAME ?= $(DEV_DOCKER_TAG_BASE)/awx_devel:$(COMPOSE_TAG)
 SRC_ONLY_PKGS ?= cffi,pycparser,psycopg2,twilio
 # These should be upgraded in the AWX and Ansible venv before attempting
 # to install the actual requirements
-VENV_BOOTSTRAP ?= pip==19.3.1 setuptools==41.6.0 wheel==0.36.2
+VENV_BOOTSTRAP ?= pip==21.2.4 setuptools==58.2.0 wheel==0.36.2
 
 NAME ?= awx
 
diff --git a/awx/main/tests/functional/test_licenses.py b/awx/main/tests/functional/test_licenses.py
index 8ff2e72bfe..d59ec0e45f 100644
--- a/awx/main/tests/functional/test_licenses.py
+++ b/awx/main/tests/functional/test_licenses.py
@@ -9,6 +9,8 @@ try:
 except ImportError:
     from pip.req import parse_requirements
 
+from pip._internal.req.constructors import parse_req_from_line
+
 
 def test_python_and_js_licenses():
     def index_licenses(path):
@@ -53,15 +55,16 @@ def test_python_and_js_licenses():
             fname = '%s/%s' % (path, req_file)
 
             for reqt in parse_requirements(fname, session=''):
-                name = reqt.name
-                version = str(reqt.specifier)
+                parsed_requirement = parse_req_from_line(reqt.requirement, None)
+                name = parsed_requirement.requirement.name
+                version = str(parsed_requirement.requirement.specifier)
                 if version.startswith('=='):
                     version = version[2:]
-                if reqt.link:
-                    if str(reqt.link).startswith(('http://', 'https://')):
-                        (name, version) = str(reqt.req).split('==', 1)
+                if parsed_requirement.link:
+                    if str(parsed_requirement.link).startswith(('http://', 'https://')):
+                        (name, version) = str(parsed_requirement.requirement).split('==', 1)
                     else:
-                        (name, version) = reqt.link.filename.split('@', 1)
+                        (name, version) = parsed_requirement.link.filename.split('@', 1)
                     if name.endswith('.git'):
                         name = name[:-4]
                     if name == 'receptor':
diff --git a/docs/licenses/tacacs-plus.txt b/docs/licenses/tacacs_plus.txt
similarity index 100%
rename from docs/licenses/tacacs-plus.txt
rename to docs/licenses/tacacs_plus.txt
diff --git a/requirements/requirements.in b/requirements/requirements.in
index 68cb3852df..6104cb3a59 100644
--- a/requirements/requirements.in
+++ b/requirements/requirements.in
@@ -57,8 +57,8 @@ twisted[tls]>=20.3.0  # CVE-2020-10108, CVE-2020-10109
 uWSGI
 uwsgitop
 wheel
-pip==19.3.1  # see UPGRADE BLOCKERs
-setuptools==41.6.0  # see UPGRADE BLOCKERs
+pip==21.2.4  # see UPGRADE BLOCKERs
+setuptools==58.2.0  # see UPGRADE BLOCKERs
 
 # Temporarily added to use ansible-runner from git branch, to be removed
 # when ansible-runner moves from requirements_git.txt to here
diff --git a/requirements/requirements.txt b/requirements/requirements.txt
index b7e9781d4b..304b73f8a5 100644
--- a/requirements/requirements.txt
+++ b/requirements/requirements.txt
@@ -412,9 +412,9 @@ zope.interface==5.0.0
     # via twisted
 
 # The following packages are considered to be unsafe in a requirements file:
-pip==19.3.1
+pip==21.2.4
     # via -r /awx_devel/requirements/requirements.in
-setuptools==41.6.0
+setuptools==58.2.0
     # via
     #   -r /awx_devel/requirements/requirements.in
     #   asciichartpy
diff --git a/requirements/requirements_dev.txt b/requirements/requirements_dev.txt
index 6811a16fd3..532ac920c3 100644
--- a/requirements/requirements_dev.txt
+++ b/requirements/requirements_dev.txt
@@ -1,6 +1,6 @@
 django-debug-toolbar==1.11
 django-rest-swagger
-pprofile
+# pprofile - re-add once https://github.com/vpelletier/pprofile/issues/41 is addressed
 ipython==7.21.0
 unittest2
 black
@@ -14,9 +14,9 @@ pytest-xdist==1.34.0 # 2.0.0 broke zuul for some reason
 tox  # for awxkit
 logutils
 jupyter
-matplotlib
+# matplotlib - Caused issues when bumping to setuptools 58
 backports.tempfile  # support in unit tests for py32+ tempfile.TemporaryDirectory
-mockldap
+git+https://github.com/artefactual-labs/mockldap.git@master#egg=mockldap
 sdb
 remote-pdb
 gprof2dot