diff --git a/.circleci/config.yml b/.circleci/config.yml
index 05e221d..242bc5f 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -11,10 +11,10 @@ jobs:
       - run:
          name: base build
          command: |
-           docker pull debian:jessie
+           docker pull debian:stretch
            make base
            mkdir -p ~/docker
-           docker save -o ~/docker/base.tar debian:jessie dockcross/base:latest
+           docker save -o ~/docker/base.tar debian:stretch dockcross/base:latest
       - run:
          name: base test
          command: |
diff --git a/Dockerfile b/Dockerfile
new file mode 100644
index 0000000..f6de010
--- /dev/null
+++ b/Dockerfile
@@ -0,0 +1,103 @@
+FROM debian:stretch-20190326-slim
+MAINTAINER Matt McCormick "matt.mccormick@kitware.com"
+
+#include "common.debian"
+# Image build scripts
+COPY imagefiles/install-gosu-binary.sh /buildscripts/
+
+ARG DEBIAN_FRONTEND=noninteractive
+ARG REPO=http://cdn-fastly.deb.debian.org
+
+RUN \
+  bash -c "echo \"deb $REPO/debian stretch main contrib non-free\" > /etc/apt/sources.list"  && \
+  bash -c "echo \"deb $REPO/debian stretch-updates main contrib non-free\" >> /etc/apt/sources.list"  && \
+  bash -c "echo \"deb $REPO/debian-security stretch/updates main\" >> /etc/apt/sources.list" && \
+  bash -c "echo \"deb http://ftp.debian.org/debian stretch-backports main\" >> /etc/apt/sources.list" && \
+  apt-get update --yes && \
+  apt-get install --no-install-recommends --yes \
+    automake \
+    autogen \
+    bash \
+    build-essential \
+    bc \
+    bzip2 \
+    ca-certificates \
+    curl \
+    dirmngr \
+    file \
+    gettext \
+    gzip \
+    gnupg \
+    zip \
+    make \
+    ncurses-dev \
+    pkg-config \
+    libtool \
+    python \
+    python-pip \
+    rsync \
+    sed \
+    ssh \
+    bison \
+    flex \
+    tar \
+    pax \
+    vim \
+    wget \
+    xz-utils \
+    zlib1g-dev \
+  && \
+  apt-get clean --yes && \
+  /buildscripts/install-gosu-binary.sh && \
+  rm -rf /buildscripts
+
+#include "common.docker"
+WORKDIR /usr/src
+
+ARG GIT_VERSION=2.20.1
+ARG CMAKE_VERSION=3.13.2
+
+# Image build scripts
+COPY \
+  imagefiles/build-and-install-cmake.sh \
+  imagefiles/build-and-install-curl.sh \
+  imagefiles/build-and-install-git.sh \
+  imagefiles/build-and-install-ninja.sh \
+  imagefiles/build-and-install-openssl.sh \
+  imagefiles/build-and-install-openssh.sh \
+  imagefiles/install-cmake-binary.sh \
+  imagefiles/install-liquidprompt-binary.sh \
+  imagefiles/install-python-packages.sh \
+  imagefiles/utils.sh \
+  /buildscripts/
+
+RUN \
+  X86_FLAG=$([ "$DEFAULT_DOCKCROSS_IMAGE" = "dockcross/manylinux-x86" ] && echo "-32" || echo "") && \
+  /buildscripts/build-and-install-openssl.sh $X86_FLAG && \
+  /buildscripts/build-and-install-openssh.sh && \
+  /buildscripts/build-and-install-curl.sh && \
+  /buildscripts/build-and-install-git.sh && \
+  /buildscripts/install-cmake-binary.sh $X86_FLAG && \
+  /buildscripts/install-liquidprompt-binary.sh && \
+  PYTHON=$([ -e /opt/python/cp35-cp35m/bin/python ] && echo "/opt/python/cp35-cp35m/bin/python" || echo "python") && \
+  /buildscripts/install-python-packages.sh -python ${PYTHON} && \
+  /buildscripts/build-and-install-ninja.sh -python ${PYTHON} && \
+  rm -rf /buildscripts
+
+RUN echo "root:root" | chpasswd
+WORKDIR /work
+ENTRYPOINT ["/dockcross/entrypoint.sh"]
+
+# Runtime scripts
+COPY imagefiles/cmake.sh /usr/local/bin/cmake
+COPY imagefiles/ccmake.sh /usr/local/bin/ccmake
+COPY imagefiles/entrypoint.sh imagefiles/dockcross /dockcross/
+
+# Build-time metadata as defined at http://label-schema.org
+# Note: To avoid systematic rebuild of dependent images, only
+#       name and vcs-url are included.
+ARG IMAGE
+ARG VCS_URL
+LABEL org.label-schema.name=$IMAGE \
+      org.label-schema.vcs-url=$VCS_URL \
+      org.label-schema.schema-version="1.0"
diff --git a/Dockerfile.in b/Dockerfile.in
index 8f5340c..2ae59c8 100644
--- a/Dockerfile.in
+++ b/Dockerfile.in
@@ -1,4 +1,4 @@
-FROM debian:jessie-20181112
+FROM debian:stretch-20190326-slim
 MAINTAINER Matt McCormick "matt.mccormick@kitware.com"
 
 #include "common.debian"
diff --git a/common.debian b/common.debian
index 0a7a7a2..40e3368 100644
--- a/common.debian
+++ b/common.debian
@@ -5,10 +5,10 @@ ARG DEBIAN_FRONTEND=noninteractive
 ARG REPO=http://cdn-fastly.deb.debian.org
 
 RUN \
-  bash -c "echo \"deb $REPO/debian jessie main contrib non-free\" > /etc/apt/sources.list"  && \
-  bash -c "echo \"deb $REPO/debian jessie-updates main contrib non-free\" >> /etc/apt/sources.list"  && \
-  bash -c "echo \"deb $REPO/debian-security jessie/updates main\" >> /etc/apt/sources.list" && \
-  bash -c "echo \"deb http://ftp.debian.org/debian jessie-backports main\" >> /etc/apt/sources.list" && \
+  bash -c "echo \"deb $REPO/debian stretch main contrib non-free\" > /etc/apt/sources.list"  && \
+  bash -c "echo \"deb $REPO/debian stretch-updates main contrib non-free\" >> /etc/apt/sources.list"  && \
+  bash -c "echo \"deb $REPO/debian-security stretch/updates main\" >> /etc/apt/sources.list" && \
+  bash -c "echo \"deb http://ftp.debian.org/debian stretch-backports main\" >> /etc/apt/sources.list" && \
   apt-get update --yes && \
   apt-get install --no-install-recommends --yes \
     automake \
@@ -19,9 +19,11 @@ RUN \
     bzip2 \
     ca-certificates \
     curl \
+    dirmngr \
     file \
     gettext \
     gzip \
+    gnupg \
     zip \
     make \
     ncurses-dev \
diff --git a/linux-ppc64le/Dockerfile b/linux-ppc64le/Dockerfile
index eaa3d51..bb2cbd8 100644
--- a/linux-ppc64le/Dockerfile
+++ b/linux-ppc64le/Dockerfile
@@ -37,9 +37,6 @@ ENV AS=/usr/bin/${CROSS_TRIPLE}-as \
 
 WORKDIR /work
 
-# Note: Toolchain file support is currently in debian Experimental according to:
-# https://wiki.debian.org/CrossToolchains#In_jessie_.28Debian_8.29
-# We can switch to that when it becomes stable.
 COPY Toolchain.cmake /usr/lib/${CROSS_TRIPLE}/
 ENV CMAKE_TOOLCHAIN_FILE /usr/lib/${CROSS_TRIPLE}/Toolchain.cmake
 
diff --git a/linux-x86/Dockerfile b/linux-x86/Dockerfile
index 8f01008..c2e500e 100644
--- a/linux-x86/Dockerfile
+++ b/linux-x86/Dockerfile
@@ -33,8 +33,6 @@ ENV AS=${CROSS_ROOT}/bin/${CROSS_TRIPLE}-as \
     CC=${CROSS_ROOT}/bin/${CROSS_TRIPLE}-gcc \
     CXX=${CROSS_ROOT}/bin/${CROSS_TRIPLE}-g++
 
-# Note: Toolchain file support is currently in debian Experimental:
-# https://wiki.debian.org/CrossToolchains#In_jessie_.28Debian_8.29
 COPY Toolchain.cmake /usr/lib/${CROSS_TRIPLE}/
 ENV CMAKE_TOOLCHAIN_FILE /usr/lib/${CROSS_TRIPLE}/Toolchain.cmake