diff --git a/packages/st2/Makefile b/packages/st2/Makefile
index c51cd396..2870c2cc 100644
--- a/packages/st2/Makefile
+++ b/packages/st2/Makefile
@@ -130,8 +130,8 @@ wheelhouse: .build-runners .stamp-wheelhouse
 .stamp-wheelhouse: | populate_version requirements inject-deps
 	cat requirements.txt
 	# Try to install wheels 2x in case the first one fails
-	$(PIP_BINARY) wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt || \
-		$(PIP_BINARY) wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt
+	$(PIP_BINARY) --use-deprecated=legacy-resolver  wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt || \
+		$(PIP_BINARY) --use-deprecated=legacy-resolver wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt
 	touch $@
 
 .build-runners:
diff --git a/packages/st2/component.makefile b/packages/st2/component.makefile
index 7b918003..f6675ee3 100644
--- a/packages/st2/component.makefile
+++ b/packages/st2/component.makefile
@@ -75,8 +75,8 @@ wheelhouse: .stamp-wheelhouse
 	# Install wheels into shared location
 	cat requirements.txt
 	# Try to install wheels 2x in case the first one fails
-	$(PIP_BINARY) wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt || \
-		$(PIP_BINARY) wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt
+	$(PIP_BINARY) --use-deprecated=legacy-resolver wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt || \
+		$(PIP_BINARY) --use-deprecated=legacy-resolver wheel --wheel-dir=$(WHEELDIR) --find-links=$(WHEELDIR) -r requirements.txt
 	touch $@
 
 bdist_wheel: .stamp-bdist_wheel
diff --git a/packages/st2/debian/rules b/packages/st2/debian/rules
index bcaf0476..2ae29880 100755
--- a/packages/st2/debian/rules
+++ b/packages/st2/debian/rules
@@ -11,6 +11,7 @@ PATH = /usr/local/sbin:/usr/local/bin:/usr/sbin:/usr/bin:/sbin:/bin
 WHEELDIR ?= /tmp/wheelhouse
 DH_VIRTUALENV_INSTALL_ROOT := /opt/stackstorm
 export DH_VIRTUALENV_INSTALL_ROOT
+PIP_VERSION = 20.3.3
 
 IS_SYSTEMD = $(shell command -v dh_systemd_enable > /dev/null 2>&1 && echo true)
 DEB_DISTRO := $(shell lsb_release -cs)
@@ -67,10 +68,11 @@ override_dh_virtualenv:
 	#
 	# NB! Use '--no-download' arg for 'virtualenv' is required,
 	# otherwise it downloads latest PIP version instead of bundled/pinned one.
-	# --force-pip-version is needed to ensure correct pip version is installed
-	# inside dh virtualenv
-	dh_virtualenv --extra-virtualenv-arg='--no-download' \
-								--force-pip-version='20.0.2' \
+	# NB! Use '--copies' else /opt/stackstorm/st2/bin/python is symlink to
+	# /usr/bin/pythonx rather than copy - and this breaks pack install
+	# which follows the path to calculate the location of the bin directory
+	dh_virtualenv --extra-virtualenv-arg='--copies' --extra-virtualenv-arg='--no-download' \
+								'--upgrade-pip-to=$(PIP_VERSION)' \
 								--extra-pip-arg '--find-links=$(WHEELDIR)' \
 								--extra-pip-arg '--no-index' --no-test
 
diff --git a/rpmspec/package_venv.spec b/rpmspec/package_venv.spec
index f25fa05f..5f5fce67 100644
--- a/rpmspec/package_venv.spec
+++ b/rpmspec/package_venv.spec
@@ -9,7 +9,7 @@
 
 %define venv_python %{venv_bin}/python3
 # https://github.com/StackStorm/st2/wiki/Where-all-to-update-pip-and-or-virtualenv
-%define pin_pip %{venv_python} %{venv_bin}/pip3 install pip==20.0.2
+%define pin_pip %{venv_python} %{venv_bin}/pip3 install pip==20.3.3
 %define install_venvctrl python3 -m pip install venvctrl
 %if 0%{?rhel} == 8
 %define install_crypto %{venv_python} %{venv_bin}/pip install cryptography==2.8 --no-binary cryptography
@@ -28,7 +28,7 @@
     virtualenv-3 -p python3 --no-download %{venv_dir} \
     %{pin_pip} \
     %{install_crypto} \
-    %{venv_pip} -r requirements.txt \
+    %{venv_pip} --use-deprecated=legacy-resolver -r requirements.txt \
     %{venv_pip} . \
     %{install_venvctrl} \
     venvctrl-relocate --source=%{venv_dir} --destination=/%{venv_install_dir} \