diff --git a/docker/tool/linux/Dockerfile b/docker/tool/linux/Dockerfile
index 14bd8d59..6bcfd1d6 100644
--- a/docker/tool/linux/Dockerfile
+++ b/docker/tool/linux/Dockerfile
@@ -1,12 +1,7 @@
 FROM iotedgedev-linux-base
 ARG IOTEDGEDEV_VERSION
 COPY iotedgedev-$IOTEDGEDEV_VERSION-py2.py3-none-any.whl dist/iotedgedev-$IOTEDGEDEV_VERSION-py2.py3-none-any.whl
-RUN pip install dist/iotedgedev-$IOTEDGEDEV_VERSION-py2.py3-none-any.whl
-RUN export LC_ALL=C.UTF-8 && \
-    export LANG=C.UTF-8
-
-RUN useradd -m iotedgedev && \
-    echo 'iotedgedev ALL=(ALL) NOPASSWD:ALL' >> /etc/sudoers && \
-    chown -R iotedgedev:iotedgedev .
-
-USER iotedgedev
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+RUN sudo -H pip3 install dist/iotedgedev-$IOTEDGEDEV_VERSION-py2.py3-none-any.whl && \
+    sudo rm -rf dist/
+ENV LC_ALL C.UTF-8
+ENV LANG C.UTF-8
\ No newline at end of file
diff --git a/docker/tool/linux/Dockerfile.base b/docker/tool/linux/Dockerfile.base
index 87ca2d7f..7fc9fa2e 100644
--- a/docker/tool/linux/Dockerfile.base
+++ b/docker/tool/linux/Dockerfile.base
@@ -27,18 +27,26 @@ RUN AZ_REPO=$(lsb_release -cs) && \
     tee /etc/apt/sources.list.d/azure-cli.list && \
     apt-key adv --keyserver packages.microsoft.com --recv-keys 52E16F86FEE04B979B07E28DB02C46DF417A0893 && \   
     apt-get update && apt-get install azure-cli
-RUN apt-get update && az extension add --name azure-cli-iot-ext && \
+RUN apt-get update && \
     npm i npm@latest -g && \
     npm i -g iothub-explorer yo generator-azure-iot-edge-module && \
     apt-get install -y --no-install-recommends python-dev build-essential libssl-dev libffi-dev libxml2-dev libxslt1-dev zlib1g-dev sudo && \
     rm -rf /var/lib/apt/lists/*
-RUN python -m pip install --upgrade pip && \
-    alias python=python3 && \
-    alias pip=pip3 && \
-    python -m pip install --upgrade pip && \
-    pip install setuptools && \
-    pip install cookiecutter
+RUN python3 -m pip install --upgrade pip && \
+    pip3 install setuptools && \
+    pip3 install cookiecutter
 WORKDIR /home/iotedge
 COPY install-dev.sh /scripts/install-dev.sh
 RUN sed -i 's/\r//' /scripts/install-dev.sh
+
+# Switch to a non-root user because Yeoman does not work root with users
+# https://github.com/Azure/iotedgedev/issues/312
+RUN useradd -m iotedgedev && \
+    echo 'iotedgedev ALL=(ALL) NOPASSWD:ALL' >> /etc/sudoers && \
+    chown -R iotedgedev:iotedgedev /home/iotedge
+USER iotedgedev
+# Azure CLI extensions are installed per user
+RUN az extension add --name azure-cli-iot-ext && \
+    echo 'alias python=python3' >> ~/.bashrc && \
+    echo 'alias pip=pip3' >> ~/.bashrc
 ENV DEBIAN_FRONTEND teletype
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