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/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