diff --git a/Install.ps1 b/Install.ps1
index 0d2e40c565..535528a121 100644
--- a/Install.ps1
+++ b/Install.ps1
@@ -102,10 +102,7 @@ foreach ($extra in $extras)
     $extras_cli += $extra
 }
 
-if (-not (Get-Item -ErrorAction SilentlyContinue ".penv/Scripts/poetry.exe").Exists)
-{
-    ./Setup-poetry.ps1 -pythonVersion "$pythonVersion"
-}
+./Setup-poetry.ps1 -pythonVersion "$pythonVersion"
 
 .penv/Scripts/poetry env use $(py -"$pythonVersion" -c 'import sys; print(sys.executable)')
 .penv/Scripts/poetry install @extras_cli
diff --git a/Setup-poetry.ps1 b/Setup-poetry.ps1
index 1b8fb305c1..b841f3f015 100644
--- a/Setup-poetry.ps1
+++ b/Setup-poetry.ps1
@@ -6,7 +6,10 @@ param(
 
 $ErrorActionPreference = "Stop"
 
-py -$pythonVersion -m venv .penv
-.penv/Scripts/python -m pip install --upgrade pip setuptools wheel
+if (-not (Get-Item -ErrorAction SilentlyContinue ".penv/Scripts/").Exists)
+{
+    py -$pythonVersion -m venv .penv
+    .penv/Scripts/python -m pip install --upgrade pip
+}
 # TODO: maybe make our own zipapp/shiv/pex of poetry and download that?
-.penv/Scripts/python -m pip install --requirement requirements-poetry.txt
+.penv/Scripts/python -m pip install --upgrade --requirement requirements-poetry.txt
diff --git a/install.sh b/install.sh
index 516e6e0845..240ec9ab0c 100755
--- a/install.sh
+++ b/install.sh
@@ -168,9 +168,7 @@ if [ "$OPENSSL_VERSION_INT" -lt "269488367" ]; then
   echo "Your OS may have patched OpenSSL and not updated the version to 1.1.1n"
 fi
 
-if [ ! -f .penv/bin/poetry ]; then
-  ./setup-poetry.sh -c "${INSTALL_PYTHON_PATH}"
-fi
+./setup-poetry.sh -c "${INSTALL_PYTHON_PATH}"
 
 .penv/bin/poetry env use "${INSTALL_PYTHON_PATH}"
 # shellcheck disable=SC2086
diff --git a/setup-poetry.sh b/setup-poetry.sh
index 76339613be..f90056371b 100755
--- a/setup-poetry.sh
+++ b/setup-poetry.sh
@@ -30,7 +30,9 @@ while getopts c:h flag; do
   esac
 done
 
-"$PYTHON_COMMAND" -m venv .penv
-.penv/bin/python -m pip install --upgrade pip setuptools wheel
+if [ ! -d .penv/bin/ ]; then
+  "$PYTHON_COMMAND" -m venv .penv
+  .penv/bin/python -m pip install --upgrade pip
+fi
 # TODO: maybe make our own zipapp/shiv/pex of poetry and download that?
-.penv/bin/python -m pip install --requirement requirements-poetry.txt
+.penv/bin/python -m pip install --upgrade --requirement requirements-poetry.txt