diff --git a/pip.sh b/pip.sh
new file mode 100755
index 0000000..9a7e6b0
--- /dev/null
+++ b/pip.sh
@@ -0,0 +1,18 @@
+#!/usr/bin/env bash
+#
+# This file is managed centrally by release-tools and should not be modified
+# within individual charm repos.  See the 'global' dir contents for available
+# choices of tox.ini for OpenStack Charms:
+#     https://github.com/openstack-charmers/release-tools
+#
+# setuptools 58.0 dropped the support for use_2to3=true which is needed to
+# install blessings (an indirect dependency of charm-tools).
+#
+# More details on the beahvior of tox and virtualenv creation can be found at
+# https://github.com/tox-dev/tox/issues/448
+#
+# This script is wrapper to force the use of the pinned versions early in the
+# process when the virtualenv was created and upgraded before installing the
+# depedencies declared in the target.
+pip install 'pip<20.3' 'setuptools<50.0.0'
+pip "$@"
diff --git a/tox.ini b/tox.ini
index 87170ca..575fab0 100644
--- a/tox.ini
+++ b/tox.ini
@@ -7,6 +7,22 @@ sitepackages = False
 # NOTE(beisner): Avoid false positives by not skipping missing interpreters.
 skip_missing_interpreters = False
 
+# NOTES:
+# * We avoid the new dependency resolver by pinning pip < 20.3, see
+#   https://github.com/pypa/pip/issues/9187
+# * Pinning dependencies requires tox >= 3.2.0, see
+#   https://tox.readthedocs.io/en/latest/config.html#conf-requires
+# * It is also necessary to pin virtualenv as a newer virtualenv would still
+#   lead to fetching the latest pip in the func* tox targets, see
+#   https://stackoverflow.com/a/38133283
+requires =
+  pip < 20.3
+  virtualenv < 20.0
+  setuptools<50.0.0
+
+# NOTE: https://wiki.canonical.com/engineering/OpenStack/InstallLatestToxOnOsci
+minversion = 3.18.0
+
 [testenv]
 basepython = python3
 setenv = VIRTUAL_ENV={envdir}
@@ -15,7 +31,7 @@ setenv = VIRTUAL_ENV={envdir}
          JUJU_REPOSITORY={envdir}/tmp/build
 passenv = http_proxy https_proxy
 install_command =
-  pip install {opts} {packages}
+  {toxinidir}/pip.sh install {opts} {packages}
 deps =
   -r{toxinidir}/requirements.txt
 whitelist_externals = /bin/true /bin/echo /bin/mkdir /bin/ln