diff --git a/diskimage_builder/elements/pip-and-virtualenv/install.d/pip-and-virtualenv-source-install/04-install-pip b/diskimage_builder/elements/pip-and-virtualenv/install.d/pip-and-virtualenv-source-install/04-install-pip
index f5ab79ee..09b49d8b 100755
--- a/diskimage_builder/elements/pip-and-virtualenv/install.d/pip-and-virtualenv-source-install/04-install-pip
+++ b/diskimage_builder/elements/pip-and-virtualenv/install.d/pip-and-virtualenv-source-install/04-install-pip
@@ -122,7 +122,10 @@ if [[ $DISTRO_NAME =~ (opensuse|fedora|centos|centos7|rhel|rhel7) ]]; then
     fi
 
     # install the latest python2 pip; this overwrites packaged pip
+    # NOTE(dpawlik) The get-pip.py script is not base on master release.
+    # Ensure that is uses latest available version.
     python /tmp/get-pip.py ${pip_args}
+    python -m pip install ${pip_args} pip
 
     # Install latest setuptools; there is a slight chicken-egg issue in
     # that pip requires setuptools for some operations like building a
@@ -141,7 +144,10 @@ if [[ $DISTRO_NAME =~ (opensuse|fedora|centos|centos7|rhel|rhel7) ]]; then
         # python2 would work -- alas get-pip.py doesn't seem to leave
         # python3 alone:
         #  https://github.com/pypa/pip/issues/4435
+        # NOTE(dpawlik) The get-pip.py script is not base on master release.
+        # Ensure that is uses latest available version.
         python3 /tmp/get-pip.py ${pip_args}
+        python3 -m pip install ${pip_args} pip
         pip3 install ${pip_args} setuptools
 
         # on < 27, this installed pip3 to /usr/bin/pip.  On >=27 it's
@@ -250,6 +256,11 @@ else
     python3 /tmp/get-pip.py $pip_args
     python2 /tmp/get-pip.py $pip_args
 
+    # NOTE(dpawlik) The get-pip.py script is not base on master release.
+    # Ensure that is uses latest available version.
+    python3 -m pip install $pip_args pip
+    python2 -m pip install $pip_args pip
+
     pip3 install $pip_args virtualenv
     pip install $pip_args virtualenv
 fi
diff --git a/diskimage_builder/elements/pip-and-virtualenv/source-repository-pip-and-virtualenv b/diskimage_builder/elements/pip-and-virtualenv/source-repository-pip-and-virtualenv
index 6d25b4c2..e74aec4b 100644
--- a/diskimage_builder/elements/pip-and-virtualenv/source-repository-pip-and-virtualenv
+++ b/diskimage_builder/elements/pip-and-virtualenv/source-repository-pip-and-virtualenv
@@ -1 +1,4 @@
-pip-and-virtualenv file /tmp/get-pip.py https://bootstrap.pypa.io/get-pip.py
+# NOTE(dpawlik) We set get-pip.py script to use 3.5 version, that is compatible
+# with python2.7 and newer. It should be removed in the future, when Python 2
+# is dropped.
+pip-and-virtualenv file /tmp/get-pip.py https://bootstrap.pypa.io/3.5/get-pip.py