diff --git a/src/almalinux/8/helix/amd64/Dockerfile b/src/almalinux/8/helix/amd64/Dockerfile
index 8bae71692..1b34638c2 100644
--- a/src/almalinux/8/helix/amd64/Dockerfile
+++ b/src/almalinux/8/helix/amd64/Dockerfile
@@ -21,10 +21,7 @@ RUN dnf upgrade --refresh -y \
         file \
     && dnf clean all
 
-RUN python3 -m pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && python3 -m pip install ./helix_scripts-*-py3-none-any.whl
-
-# Aspnetcore test runs expect python to be available without version suffix
+# Test runs expect python to be available without version suffix
 RUN alternatives --set python /usr/bin/python3 \
     && ln -sf /usr/bin/pip3 /usr/bin/pip
 
@@ -33,8 +30,14 @@ ENV LANG=en-US.UTF-8
 # create helixbot user and give rights to sudo without password
 RUN adduser --uid 1000 --shell /bin/bash --gid adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python3 -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/alpine/3.18/helix/Dockerfile b/src/alpine/3.18/helix/Dockerfile
index 658403841..b50c94814 100644
--- a/src/alpine/3.18/helix/Dockerfile
+++ b/src/alpine/3.18/helix/Dockerfile
@@ -10,7 +10,8 @@ RUN apk add --upgrade --no-cache \
 RUN python3 -m venv /venv && \
         source /venv/bin/activate && \
         pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-        pip install ./helix_scripts-*-py3-none-any.whl
+        pip install ./helix_scripts-*-py3-none-any.whl && \
+        rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/alpine:3.18
 
@@ -52,5 +53,5 @@ USER helixbot
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/alpine/3.20/helix/Dockerfile b/src/alpine/3.20/helix/Dockerfile
index ed3db3c64..167919264 100644
--- a/src/alpine/3.20/helix/Dockerfile
+++ b/src/alpine/3.20/helix/Dockerfile
@@ -12,7 +12,8 @@ RUN apk add --upgrade --no-cache \
 RUN python3 -m venv /venv && \
         source /venv/bin/activate && \
         pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-        pip install ./helix_scripts-*-py3-none-any.whl
+        pip install ./helix_scripts-*-py3-none-any.whl && \
+        rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/alpine:3.20
 
@@ -55,5 +56,5 @@ USER helixbot
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/alpine/3.21/helix/Dockerfile b/src/alpine/3.21/helix/Dockerfile
index e4ef7b6a0..be3b1c9fc 100644
--- a/src/alpine/3.21/helix/Dockerfile
+++ b/src/alpine/3.21/helix/Dockerfile
@@ -12,7 +12,8 @@ RUN apk add --upgrade --no-cache \
 RUN python3 -m venv /venv && \
         source /venv/bin/activate && \
         pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-        pip install ./helix_scripts-*-py3-none-any.whl
+        pip install ./helix_scripts-*-py3-none-any.whl && \
+        rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/alpine:3.21
 
@@ -53,5 +54,5 @@ USER helixbot
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/azurelinux/3.0/helix/Dockerfile b/src/azurelinux/3.0/helix/Dockerfile
index dfe4cecf6..bac125136 100644
--- a/src/azurelinux/3.0/helix/Dockerfile
+++ b/src/azurelinux/3.0/helix/Dockerfile
@@ -12,8 +12,8 @@ RUN tdnf install --refresh -y \
 RUN python3 -m venv /venv && \
         source /venv/bin/activate && \
         pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-        pip install ./helix_scripts-*-py3-none-any.whl
-
+        pip install ./helix_scripts-*-py3-none-any.whl && \
+        rm ./helix_scripts-*-py3-none-any.whl
 
 FROM mcr.microsoft.com/azurelinux/base/core:3.0
 
@@ -29,6 +29,7 @@ RUN tdnf install --setopt tsflags=nodocs --refresh -y \
         python3 \
         python3-pip \
         shadow-utils \
+        sudo \
         tar \
         tzdata \
         which \
@@ -37,7 +38,7 @@ RUN tdnf install --setopt tsflags=nodocs --refresh -y \
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/useradd -c '' --uid 1000 --shell /bin/bash --groups adm helixbot && \
     chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" >> /etc/sudoers && \
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot && \
     mkdir /home/helixbot/ && chown -R helixbot /home/helixbot/
 
 USER helixbot
@@ -45,5 +46,5 @@ USER helixbot
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/cbl-mariner/2.0/helix/amd64/Dockerfile b/src/cbl-mariner/2.0/helix/amd64/Dockerfile
index 3c4c9b2fd..41d414431 100644
--- a/src/cbl-mariner/2.0/helix/amd64/Dockerfile
+++ b/src/cbl-mariner/2.0/helix/amd64/Dockerfile
@@ -13,23 +13,27 @@ RUN tdnf install --setopt tsflags=nodocs --refresh -y \
          llvm \
          python3-pip \
          shadow-utils \
+         sudo \
          tar \
          tzdata \
          which \
     && tdnf clean all
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python && \
-    python -m pip install --upgrade setuptools && \
-    pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-    pip install ./helix_scripts-*-py3-none-any.whl && \
-    rm ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/useradd -c '' --uid 1000 --shell /bin/bash --groups adm helixbot && \
     chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" >> /etc/sudoers && \
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot && \
     mkdir /home/helixbot/ && chown -R helixbot /home/helixbot/
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install --upgrade pip && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/centos-stream/10/helix/Dockerfile b/src/centos-stream/10/helix/Dockerfile
index 38b654d78..6d4c14a6f 100644
--- a/src/centos-stream/10/helix/Dockerfile
+++ b/src/centos-stream/10/helix/Dockerfile
@@ -11,8 +11,9 @@ RUN dnf upgrade --refresh -y \
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
-    
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
+
 FROM quay.io/centos/centos:stream10
 
 # Install dependencies
@@ -50,12 +51,12 @@ ENV LANG=en_US.utf8
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/adduser --uid 1000 --shell /bin/bash --gid adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
 # Install Helix Dependencies
-ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/centos-stream/9/helix/amd64/Dockerfile b/src/centos-stream/9/helix/amd64/Dockerfile
index da8260f34..6fcb25154 100644
--- a/src/centos-stream/9/helix/amd64/Dockerfile
+++ b/src/centos-stream/9/helix/amd64/Dockerfile
@@ -32,17 +32,21 @@ RUN dnf upgrade --refresh -y \
         which \
     && dnf clean all
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python \
-    && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
 ENV LANG=en_US.utf8
 
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/adduser --uid 1000 --shell /bin/bash --gid adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/centos-stream/9/mlnet/helix/amd64/Dockerfile b/src/centos-stream/9/mlnet/helix/amd64/Dockerfile
index d97eaea99..aeb8601b0 100644
--- a/src/centos-stream/9/mlnet/helix/amd64/Dockerfile
+++ b/src/centos-stream/9/mlnet/helix/amd64/Dockerfile
@@ -46,6 +46,7 @@ RUN dnf upgrade --refresh -y \
         procps-ng \
         python3 \
         python3-devel \
+        python3-pip \
         readline-devel \
         sudo \
         swig \
@@ -82,17 +83,21 @@ RUN wget http://releases.llvm.org/3.9.1/openmp-3.9.1.src.tar.xz \
 # Sets the library path to pickup openmp
 ENV LD_LIBRARY_PATH=/usr/local/lib:/usr/local/lib64
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python \
-    && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
 ENV LANG=en_US.utf8
 
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/adduser --uid 1000 --shell /bin/bash --gid adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
\ No newline at end of file
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/debian/11/helix/amd64/Dockerfile b/src/debian/11/helix/amd64/Dockerfile
index 65857407a..7f14dddc9 100644
--- a/src/debian/11/helix/amd64/Dockerfile
+++ b/src/debian/11/helix/amd64/Dockerfile
@@ -42,16 +42,20 @@ RUN apt-get update \
 
 ENV LANG=en_US.utf8
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python \
-    && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
 # Create helixbot user and give rights to sudo without password
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install --upgrade pip && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/debian/11/helix/arm64v8/Dockerfile b/src/debian/11/helix/arm64v8/Dockerfile
index 4ed013917..26049bd0b 100644
--- a/src/debian/11/helix/arm64v8/Dockerfile
+++ b/src/debian/11/helix/arm64v8/Dockerfile
@@ -43,20 +43,20 @@ RUN apt-get update \
 
 ENV LANG=en_US.utf8
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python \
-    && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && export CRYPTOGRAPHY_DONT_BUILD_RUST=1 \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
-# Create helixbot users and give rights to sudo without password
-# (we use two users here to ensure volume mounting works with two possible UIDs of the host UID)
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
-RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1001 --shell /bin/bash --ingroup adm helixbot \
-    && /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot2 \
+# Create helixbot user and give rights to sudo without password
+RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers \
-    && echo "helixbot2 ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers 
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install --upgrade pip && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/debian/12/helix/amd64/Dockerfile b/src/debian/12/helix/amd64/Dockerfile
index 9bfb114d0..eaf09ac89 100644
--- a/src/debian/12/helix/amd64/Dockerfile
+++ b/src/debian/12/helix/amd64/Dockerfile
@@ -12,7 +12,8 @@ RUN apt-get update \
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/debian:bookworm
 
@@ -59,15 +60,14 @@ RUN apt-get update \
 ENV LANG=en_US.utf8
 
 # Create helixbot user and give rights to sudo without password
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/debian/12/helix/arm32v7/Dockerfile b/src/debian/12/helix/arm32v7/Dockerfile
index da99d6dcd..f2a548c32 100644
--- a/src/debian/12/helix/arm32v7/Dockerfile
+++ b/src/debian/12/helix/arm32v7/Dockerfile
@@ -21,7 +21,8 @@ ENV PATH="/root/.cargo/bin:${PATH}"
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/debian:bookworm
 
@@ -68,15 +69,14 @@ RUN apt-get update \
 ENV LANG=en_US.utf8
 
 # Create helixbot user and give rights to sudo without password
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/debian/12/helix/arm64v8/Dockerfile b/src/debian/12/helix/arm64v8/Dockerfile
index 510e8ce46..ff1bdccf0 100644
--- a/src/debian/12/helix/arm64v8/Dockerfile
+++ b/src/debian/12/helix/arm64v8/Dockerfile
@@ -12,7 +12,8 @@ RUN apt-get update \
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/debian:bookworm
 
@@ -58,15 +59,14 @@ RUN apt-get update \
 ENV LANG=en_US.utf8
 
 # Create helixbot user and give rights to sudo without password
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/debian/13/helix/Dockerfile b/src/debian/13/helix/Dockerfile
index b49c0c22a..e73e093a6 100644
--- a/src/debian/13/helix/Dockerfile
+++ b/src/debian/13/helix/Dockerfile
@@ -15,7 +15,8 @@ RUN apt-get update \
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/debian:trixie
 ARG TARGETARCH
@@ -73,15 +74,14 @@ RUN ARCH=$TARGETARCH \
 ENV LANG=en_US.utf8
 
 # Create helixbot user and give rights to sudo without password
-# additionally, preinstall the virtualenv packages used for VSTS reporting to save time
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/fedora/41/helix/amd64/Dockerfile b/src/fedora/41/helix/amd64/Dockerfile
index 0b526b55a..bb8271ad1 100644
--- a/src/fedora/41/helix/amd64/Dockerfile
+++ b/src/fedora/41/helix/amd64/Dockerfile
@@ -14,9 +14,9 @@ RUN dnf upgrade --refresh -y \
 
 RUN python3 -m venv /venv \
     && source /venv/bin/activate \
-    pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM library/fedora:41
 
@@ -62,11 +62,13 @@ ENV LANG=en-US.UTF-8
 # Fedora does not have all options as other Linux systems
 RUN /usr/sbin/adduser --uid 1000 --shell /bin/bash --group adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers \
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot \
     && chmod +s /usr/bin/ping
 
-# Install Helix Dependencies
+USER helixbot
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
+
+# Install Helix Dependencies
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
diff --git a/src/opensuse/15.6/helix/amd64/Dockerfile b/src/opensuse/15.6/helix/amd64/Dockerfile
index f646a0b42..aca58128b 100644
--- a/src/opensuse/15.6/helix/amd64/Dockerfile
+++ b/src/opensuse/15.6/helix/amd64/Dockerfile
@@ -45,15 +45,19 @@ RUN wget https://packages.microsoft.com/keys/microsoft.asc \
         libmsquic \
     && zypper clean -a
 
-RUN ln -sf /usr/bin/python3.12 /usr/bin/python \
-    && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3.12 /usr/bin/python
 
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/useradd --uid 1000 --shell /bin/bash --system --create-home --groups trusted helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/ubuntu/20.04/helix/Dockerfile b/src/ubuntu/20.04/helix/Dockerfile
index 7e55a1542..357c8732e 100644
--- a/src/ubuntu/20.04/helix/Dockerfile
+++ b/src/ubuntu/20.04/helix/Dockerfile
@@ -27,9 +27,9 @@ RUN apt-get update && \
         llvm \
         locales \
         locales-all \
-        python3-dev \
+        python3.9-dev \
         python3-pip \
-        python3-venv \
+        python3.9-venv \
         software-properties-common \
         sudo \
         tzdata \
@@ -41,9 +41,7 @@ RUN apt-get update && \
 
 ENV LANG=en_US.utf8
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python && \
-    pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-    pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3.9 /usr/bin/python
 
 # Add MsQuic
 RUN curl -LO https://packages.microsoft.com/keys/microsoft.asc && \
@@ -58,8 +56,14 @@ RUN curl -LO https://packages.microsoft.com/keys/microsoft.asc && \
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot && \
     chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/ubuntu/20.04/helix/sqlserver/amd64/Dockerfile b/src/ubuntu/20.04/helix/sqlserver/amd64/Dockerfile
index 6d424c3d6..5ab8eb46b 100644
--- a/src/ubuntu/20.04/helix/sqlserver/amd64/Dockerfile
+++ b/src/ubuntu/20.04/helix/sqlserver/amd64/Dockerfile
@@ -25,4 +25,4 @@ RUN groupadd -g 1000 sqlserver_users \
 
 CMD ["/opt/mssql/bin/sqlservr"]
 
-USER helixbot
\ No newline at end of file
+USER helixbot
diff --git a/src/ubuntu/20.04/helix/wasm/amd64/Dockerfile b/src/ubuntu/20.04/helix/wasm/amd64/Dockerfile
index 1abade825..0737598c4 100644
--- a/src/ubuntu/20.04/helix/wasm/amd64/Dockerfile
+++ b/src/ubuntu/20.04/helix/wasm/amd64/Dockerfile
@@ -8,7 +8,7 @@ USER root
 
 RUN apt-get clean && \
     mv /etc/apt/sources.list /etc/apt/sources.list1 && apt-get update && \
-    mv /etc/apt/sources.list1 /etc/apt/sources.list &&  apt-get update && \
+    mv /etc/apt/sources.list1 /etc/apt/sources.list && apt-get update && \
     apt-get install -qq -y \
         libnode-dev \
         curl \
@@ -17,7 +17,6 @@ RUN apt-get clean && \
      \
      && localedef -i en_US -c -f UTF-8 -A /usr/share/locale/locale.alias en_US.UTF-8
 
-
 # update node, which is required for newer npm, jsvu and v8
 COPY ./setup-node-23.x.sh /tmp
 RUN /tmp/setup-node-23.x.sh && apt-get -y install nodejs
diff --git a/src/ubuntu/22.04/helix/Dockerfile b/src/ubuntu/22.04/helix/Dockerfile
index 1f23cc4e1..60d18cef5 100644
--- a/src/ubuntu/22.04/helix/Dockerfile
+++ b/src/ubuntu/22.04/helix/Dockerfile
@@ -40,9 +40,7 @@ RUN apt-get update && \
 
 ENV LANG=en_US.utf8
 
-RUN ln -sf /usr/bin/python3 /usr/bin/python && \
-    pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-    pip install ./helix_scripts-*-py3-none-any.whl
+RUN ln -sf /usr/bin/python3 /usr/bin/python
 
 # Add MsQuic
 RUN curl -LO https://packages.microsoft.com/keys/microsoft.asc && \
@@ -57,8 +55,14 @@ RUN curl -LO https://packages.microsoft.com/keys/microsoft.asc && \
 # create helixbot user and give rights to sudo without password
 RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot && \
     chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 
-RUN python -m venv /home/helixbot/.vsts-env
+RUN python -m venv /home/helixbot/.vsts-env && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/ubuntu/22.04/mlnet/helix/amd64/Dockerfile b/src/ubuntu/22.04/mlnet/helix/amd64/Dockerfile
index add7e30e2..13b29c35b 100644
--- a/src/ubuntu/22.04/mlnet/helix/amd64/Dockerfile
+++ b/src/ubuntu/22.04/mlnet/helix/amd64/Dockerfile
@@ -1,21 +1,25 @@
-FROM mcr.microsoft.com/dotnet-buildtools/prereqs:ubuntu-22.04-mlnet
-
-# Install Helix Dependencies
-RUN apt-get update \
-    && apt-get install -y \
-        python3-pip \
-        python3-venv \
-    && rm -rf /var/lib/apt/lists/*
-
-RUN ln -sf /usr/bin/python3 /usr/bin/python && \
-    pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-    pip install ./helix_scripts-*-py3-none-any.whl
-
-# create helixbot user and give rights to sudo without password
-RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot && \
-    chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
-
-USER helixbot
-
-RUN python -m venv /home/helixbot/.vsts-env
+FROM mcr.microsoft.com/dotnet-buildtools/prereqs:ubuntu-22.04-mlnet
+
+# Install Helix Dependencies
+RUN apt-get update \
+    && apt-get install -y \
+        python3-pip \
+        python3-venv \
+    && rm -rf /var/lib/apt/lists/*
+
+RUN ln -sf /usr/bin/python3 /usr/bin/python
+
+# create helixbot user and give rights to sudo without password
+RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot && \
+    chmod 755 /root && \
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
+
+USER helixbot
+WORKDIR /home/helixbot
+ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
+
+RUN python -m venv $VIRTUAL_ENV && \
+    ${VIRTUAL_ENV}/bin/pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
+    ${VIRTUAL_ENV}/bin/pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
diff --git a/src/ubuntu/24.04/helix/Dockerfile b/src/ubuntu/24.04/helix/Dockerfile
index 84f0dff5b..c9dbba9e1 100644
--- a/src/ubuntu/24.04/helix/Dockerfile
+++ b/src/ubuntu/24.04/helix/Dockerfile
@@ -16,7 +16,8 @@ RUN apt-get update && \
 RUN python3 -m venv /venv && \
     . /venv/bin/activate && \
     pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple && \
-    pip install ./helix_scripts-*-py3-none-any.whl
+    pip install ./helix_scripts-*-py3-none-any.whl && \
+    rm ./helix_scripts-*-py3-none-any.whl
 
 FROM ubuntu.azurecr.io/ubuntu:noble
 ARG TARGETARCH
@@ -24,7 +25,7 @@ ENV DEBIAN_FRONTEND=noninteractive
 
 RUN LIBCURL=libcurl4 && \
     if [ "$TARGETARCH" = "arm" ]; then \
-        LIBCURL="libcurl4t64"; fi && \ 
+        LIBCURL="libcurl4t64"; fi && \
     apt-get update && \
     apt-get install -qq -y \
         autoconf \
@@ -73,16 +74,19 @@ RUN curl -LO https://packages.microsoft.com/keys/microsoft.asc && \
     apt-get install -y libmsquic && \
     rm -rf /var/lib/apt/lists/*
 
+# Remove user (probably ubuntu) with UID 1000 to UID 2000 to avoid conflict with helixbot
+RUN user_id=$(id -un 1000) && \
+    /usr/sbin/userdel --force --remove $user_id
+
 # create helixbot user and give rights to sudo without password
-RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1001 --shell /bin/bash --ingroup adm helixbot && \
+RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot && \
     chmod 755 /root && \
-    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV
-
diff --git a/src/ubuntu/24.10/helix/Dockerfile b/src/ubuntu/24.10/helix/Dockerfile
index b6aa30f94..ce1c1be47 100644
--- a/src/ubuntu/24.10/helix/Dockerfile
+++ b/src/ubuntu/24.10/helix/Dockerfile
@@ -16,7 +16,8 @@ RUN apt-get update \
 RUN python3 -m venv /venv \
     && . /venv/bin/activate \
     && pip download --no-deps helix-scripts --index-url https://dnceng.pkgs.visualstudio.com/public/_packaging/helix-client-prod/pypi/simple \
-    && pip install ./helix_scripts-*-py3-none-any.whl
+    && pip install ./helix_scripts-*-py3-none-any.whl \
+    && rm ./helix_scripts-*-py3-none-any.whl
 
 FROM ubuntu.azurecr.io/ubuntu:oracular
 ARG TARGETARCH
@@ -24,7 +25,7 @@ ENV DEBIAN_FRONTEND=noninteractive
 
 RUN LIBCURL=libcurl4 \
     && if [ "$TARGETARCH" = "arm" ]; then \
-         LIBCURL="libcurl4t64"; fi \ 
+         LIBCURL="libcurl4t64"; fi \
     && apt-get update \
     && apt-get install -qq -y \
         autoconf \
@@ -76,15 +77,19 @@ RUN ARCH=$TARGETARCH \
     && dpkg -i libmsquic* \
     && rm libmsquic*
 
+# Remove user (probably ubuntu) with UID 1000 to UID 2000 to avoid conflict with helixbot
+RUN user_id=$(id -un 1000) && \
+    /usr/sbin/userdel --force --remove $user_id
+
 # create helixbot user and give rights to sudo without password
-RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1001 --shell /bin/bash --ingroup adm helixbot \
+RUN /usr/sbin/adduser --disabled-password --gecos '' --uid 1000 --shell /bin/bash --ingroup adm helixbot \
     && chmod 755 /root \
-    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers
+    && echo "helixbot ALL=(ALL)       NOPASSWD: ALL" > /etc/sudoers.d/helixbot
 
 USER helixbot
 
 # Install Helix Dependencies
 ENV VIRTUAL_ENV=/home/helixbot/.vsts-env
 RUN python3 -m venv $VIRTUAL_ENV
-ENV PATH="$VIRTUAL_ENV/bin:$PATH"
+ENV PATH="${VIRTUAL_ENV}/bin:${PATH}"
 COPY --from=venv --chown=helixbot /venv $VIRTUAL_ENV