diff --git a/README.md b/README.md
index 7badb74..988c058 100644
--- a/README.md
+++ b/README.md
@@ -70,3 +70,14 @@ pipenv
 ```
 
 You can specify a non-default location of this file by setting a `ASDF_PYTHON_DEFAULT_PACKAGES_FILE` variable.
+
+### Upgrade pip before installing Default Python packages
+
+In some cases (older verisons of pip - which come with older versions of Python) unpinned package versions in `$HOME/.default-python-packages` (or `ASDF_PYTHON_DEFAULT_PACKAGES_FILE` environment variable) may cause errors during pip install - due to latest package dependency versions not being available.
+
+You can set the environment variable `ASDF_PYTHON_PKGS_UPGRADE_PIP_FIRST` (to either `true` or `True`) to first upgrade your pip version, before installing pacakges from `$HOME/.default-python-packages` (or `ASDF_PYTHON_DEFAULT_PACKAGES_FILE` environment variable):
+
+```
+export ASDF_PYTHON_PKGS_UPGRADE_PIP_FIRST=true
+asdf install python 3.6.15
+```
diff --git a/bin/install b/bin/install
index 3c4219c..2963508 100755
--- a/bin/install
+++ b/bin/install
@@ -34,6 +34,10 @@ install_default_python_packages() {
   local packages_file="${ASDF_PYTHON_DEFAULT_PACKAGES_FILE:-$HOME/.default-python-packages}"
 
   if [ -f "$packages_file" ]; then
+    if [[ "${ASDF_PYTHON_PKGS_UPGRADE_PIP_FIRST:-}" =~ ^t|True ]]; then
+        echo "pip install --upgrade pip"
+        PATH="$ASDF_INSTALL_PATH/bin:$PATH" pip install --upgrade pip
+    fi
     echo -ne "\nInstalling default python packages..."
     PATH="$ASDF_INSTALL_PATH/bin:$PATH" pip install -U -r "$packages_file"
   fi