diff --git a/Dockerfile b/Dockerfile
index 67a5c1f..9d42b7e 100644
--- a/Dockerfile
+++ b/Dockerfile
@@ -1,82 +1,122 @@
 ARG CRYSTAL_VERSION=1.0.0
-FROM crystallang/crystal:${CRYSTAL_VERSION} as build
 
-ARG PLACE_COMMIT=DEV
+# Digest CLI
+###############################################################################
+FROM crystallang/crystal:${CRYSTAL_VERSION} as digest
+
+ARG CRYSTAL_VERSION=1.0.0
+ARG PLACE_COMMIT="DEV"
 
 WORKDIR /app
 
-RUN apt update
-RUN apt install --no-install-recommends -y \
+RUN apt-get update && \
+    apt-get install -y apt-transport-https && \
+    apt-get update && \
+    DEBIAN_FRONTEND=noninteractive \
+    apt install --no-install-recommends -y \
         bash \
         ca-certificates \
         curl \
-        git \
-        libssh2-1 libssh2-1-dev \
-        libgc-dev \
         llvm-10 llvm-10-dev \
-        tzdata
+        libssh2-1 libssh2-1-dev \
+        libyaml-dev \
+    && apt-get clean && rm -rf /var/lib/apt/lists/* /tmp/* /var/tmp/*
 
-# Add trusted CAs for communicating with external services
-RUN update-ca-certificates
+# Install shards before adding source.
+COPY shard.yml /app
+COPY shard.lock /app
+RUN shards install --ignore-crystal-version
 
-# Create a non-privileged user
-ARG IMAGE_UID="10001"
-ENV UID=$IMAGE_UID
-ENV USER=appuser
-RUN adduser \
-    --disabled-password \
-    --gecos "" \
-    --home "/nonexistent" \
-    --shell "/sbin/nologin" \
-    --no-create-home \
-    --uid "${UID}" \
-    "${USER}"
+# Build digest tool before copying rest of source for better caching.
+COPY src/digest_cli.cr /app/src/digest_cli.cr
+RUN CRYSTAL_PATH=lib:/usr/share/crystal/src/ \
+    LLVM_CONFIG=$(/usr/share/crystal/src/llvm/ext/find-llvm-config) \
+    shards build digest_cli -Dpreview_mt --ignore-crystal-version --no-debug --production
 
-# These provide certificate chain validation where communicating with external services over TLS
-ENV SSL_CERT_FILE=/etc/ssl/certs/ca-certificates.crt
+# Extract dependencies
+RUN ldd /app/bin/digest_cli | tr -s '[:blank:]' '\n' | grep '^/' | xargs -I % sh -c 'mkdir -p $(dirname deps%); cp % deps%;'
 
-# Create binary directories
-RUN mkdir -p repositories bin/drivers
+# Build
+###############################################################################
 
-RUN mkdir /app/.shards
+FROM crystallang/crystal:${CRYSTAL_VERSION}-alpine as build
 
-# Install deps
-COPY shard.yml /app
-COPY shard.lock /app
+ARG CRYSTAL_VERSION=1.0.0
+ARG PLACE_COMMIT="DEV"
 
-RUN shards install --production --ignore-crystal-version
+WORKDIR /app
 
-# Copy source for the long building `digest_cli`
-RUN mkdir /app/src
-COPY src/digest_cli.cr /app/src/digest_cli.cr
+# Install the latest version of LibSSH2, ping, etc
+RUN apk add --no-cache \
+    bash \
+    ca-certificates \
+    curl \
+    iputils \
+    libssh2-static \
+    yaml-static
+
+# Add a glibc shim
+# NOTE: Once musl builds are a supported target, `asdf` should be updated to use those builds
+RUN mkdir keys && (cd keys && curl -slO https://alpine-pkgs.sgerrand.com/sgerrand.rsa.pub) && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-i18n-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-bin-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-dev-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-dev-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-bin-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-i18n-2.33-r0.apk && \
+    rm -r keys *.apk
 
-RUN CRYSTAL_PATH=lib:/usr/share/crystal/src/ \
-    LLVM_CONFIG=$(/usr/share/crystal/src/llvm/ext/find-llvm-config) \
-    PLACE_COMMIT=${PLACE_COMMIT} \
-    UNAME_AT_COMPILE_TIME=true \
-    shards build --error-trace --ignore-crystal-version --release --production -Dpreview_mt digest_cli
+# Add trusted CAs for communicating with external services
+RUN update-ca-certificates
+
+# Install shards before adding source.
+COPY shard.yml /app
+COPY shard.lock /app
+RUN shards install --ignore-crystal-version
+
+# Copy the `digest_cli` binary, and all of its runtime dependencies
+COPY --from=digest /app/deps /
+COPY --from=digest /app/bin/digest_cli /app/bin
 
 # Add the rest of the source last for efficient caching
+COPY scripts /app/scripts
 COPY src /app/src
 
 RUN PLACE_COMMIT=${PLACE_COMMIT} \
     UNAME_AT_COMPILE_TIME=true \
-    shards build --error-trace --ignore-crystal-version --release --production -Dpreview_mt build
-
-RUN chown appuser -R /app
+    shards build --error-trace -Dpreview_mt --release --ignore-crystal-version --production build
 
 ###############################################################################
 
-USER appuser:appuser
+ENV HOME="/app"
+ENV CRYSTAL_VERSION=$CRYSTAL_VERSION
+ENV SSL_CERT_FILE=/etc/ssl/certs/ca-certificates.crt
+
+# Create a non-privileged user
+ARG IMAGE_UID="10001"
+ENV UID=$IMAGE_UID
+ENV USER=appuser
+RUN adduser \
+    --disabled-password \
+    --gecos "" \
+    --home "${HOME}" \
+    --shell "/sbin/nologin" \
+    --uid "${UID}" \
+    "${USER}"
 
 # Install asdf version manager
 SHELL ["/bin/bash", "-l", "-c"]
-RUN git clone https://github.com/asdf-vm/asdf.git $HOME/.asdf --branch v0.8.0
-RUN $HOME/.asdf/bin/asdf plugin-add crystal https://github.com/asdf-community/asdf-crystal.git
-RUN echo -e '\n. $HOME/.asdf/asdf.sh' >> ~/.bashrc && \
+RUN git clone --depth 1 https://github.com/asdf-vm/asdf.git $HOME/.asdf --branch v0.8.0 && \
+    $HOME/.asdf/bin/asdf plugin-add crystal https://github.com/asdf-community/asdf-crystal.git && \
+    echo -e '\n. $HOME/.asdf/asdf.sh' >> ~/.bashrc && \
     echo -e '\n. $HOME/.asdf/asdf.sh' >> ~/.profile && \
     source ~/.bashrc
 
+RUN chown appuser -R "${HOME}"
+USER appuser:appuser
+
 EXPOSE 3000
 HEALTHCHECK CMD wget -qO- http://localhost:3000/api/build/v1
 CMD ["/app/scripts/entrypoint.sh", "--server", "-b", "0.0.0.0", "-p", "3000"]
diff --git a/Dockerfile.test b/Dockerfile.test
index 0d175a8..66802ef 100644
--- a/Dockerfile.test
+++ b/Dockerfile.test
@@ -1,25 +1,26 @@
 ARG CRYSTAL_VERSION=1.0.0
-FROM crystallang/crystal:${CRYSTAL_VERSION}
 
+# Digest CLI
+###############################################################################
+FROM crystallang/crystal:${CRYSTAL_VERSION} as digest
+
+ARG CRYSTAL_VERSION=1.0.0
 ARG PLACE_COMMIT="DEV"
 
 WORKDIR /app
 
-RUN apt update
-RUN apt install --no-install-recommends -y \
+RUN apt-get update && \
+    apt-get install -y apt-transport-https && \
+    apt-get update && \
+    DEBIAN_FRONTEND=noninteractive \
+    apt install --no-install-recommends -y \
         bash \
         ca-certificates \
         curl \
-        libssh2-1 libssh2-1-dev \
         llvm-10 llvm-10-dev \
-
-# Install watchexec
-RUN curl -sLO https://github.com/watchexec/watchexec/releases/download/cli-v1.16.0/watchexec-1.16.0-x86_64-unknown-linux-gnu.deb && \
-    dpkg -i watchexec-1.16.0-x86_64-unknown-linux-gnu.deb && \
-    rm -rf ./*.deb
-
-# Add trusted CAs for communicating with external services
-RUN update-ca-certificates
+        libssh2-1 libssh2-1-dev \
+        libyaml-dev \
+    && apt-get clean && rm -rf /var/lib/apt/lists/* /tmp/* /var/tmp/*
 
 # Install shards before adding source.
 COPY shard.yml /app
@@ -27,29 +28,81 @@ COPY shard.lock /app
 RUN shards install --ignore-crystal-version
 
 # Build digest tool before copying rest of source for better caching.
-RUN mkdir /app/src
 COPY src/digest_cli.cr /app/src/digest_cli.cr
-
 RUN CRYSTAL_PATH=lib:/usr/share/crystal/src/ \
     LLVM_CONFIG=$(/usr/share/crystal/src/llvm/ext/find-llvm-config) \
-    shards build digest_cli --ignore-crystal-version --no-debug
+    shards build digest_cli -Dpreview_mt --ignore-crystal-version --no-debug --production
 
-COPY src/digest_cli.cr /app/src/digest_cli.cr
+# Extract dependencies
+RUN ldd /app/bin/digest_cli | tr -s '[:blank:]' '\n' | grep '^/' | xargs -I % sh -c 'mkdir -p $(dirname deps%); cp % deps%;'
 
-COPY scripts /app/scripts
-COPY src /app/sr
+# Build
+###############################################################################
+
+FROM crystallang/crystal:${CRYSTAL_VERSION}-alpine as build
+
+ARG CRYSTAL_VERSION=1.0.0
+ARG PLACE_COMMIT="DEV"
+
+WORKDIR /app
+
+# Install the latest version of LibSSH2, ping, etc
+RUN apk add --no-cache \
+    bash \
+    ca-certificates \
+    curl \
+    iputils \
+    libssh2-static \
+    yaml-static
 
-RUN mkdir -p /app/bin/drivers
+# Add a glibc shim
+# NOTE: Once musl builds are a supported target, `asdf` should be updated to use those builds
+RUN mkdir keys && (cd keys && curl -slO https://alpine-pkgs.sgerrand.com/sgerrand.rsa.pub) && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-i18n-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-bin-2.33-r0.apk && \
+    curl -sLO https://github.com/sgerrand/alpine-pkg-glibc/releases/download/2.33-r0/glibc-dev-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-dev-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-bin-2.33-r0.apk && \
+    apk add --allow-untrusted --keys-dir keys glibc-i18n-2.33-r0.apk && \
+    rm -r keys *.apk
+
+# Add trusted CAs for communicating with external services
+RUN update-ca-certificates
+
+# Add watchexec
+RUN apk add --no-cache -X http://dl-cdn.alpinelinux.org/alpine/edge/testing watchexec
+
+# Install shards before adding source.
+COPY shard.yml /app
+COPY shard.lock /app
+RUN shards install --ignore-crystal-version
+
+# Copy the `digest_cli` binary, and all of its runtime dependencies
+COPY --from=digest /app/deps /
+COPY --from=digest /app/bin/digest_cli /app/bin
+
+COPY scripts /app/scripts
+COPY src /app/src
 
 # These provide certificate chain validation where communicating with external services over TLS
 ENV SSL_CERT_FILE=/etc/ssl/certs/ca-certificates.crt
 
-# Install asdf version manager
+###############################################3###############################
+
+ENV CRYSTAL_PATH=lib:/usr/share/crystal/src
+ENV CRYSTAL_LIBRARY_PATH=/usr/local/lib
+ENV CRYSTAL_VERSION=${CRYSTAL_VERSION}
+
+ENV HOME="/app"
 SHELL ["/bin/bash", "-l", "-c"]
-RUN git clone https://github.com/asdf-vm/asdf.git $HOME/.asdf --branch v0.8.0 && \
+
+# Install asdf version manager
+RUN git clone --depth 1 https://github.com/asdf-vm/asdf.git $HOME/.asdf --branch v0.8.0 && \
     $HOME/.asdf/bin/asdf plugin-add crystal https://github.com/asdf-community/asdf-crystal.git && \
-    echo -e '\n. $HOME/.asdf/asdf.sh' >> ~/.bashrc && \
-    echo -e '\n. $HOME/.asdf/asdf.sh' >> ~/.profile && \
+    echo -e '\n. $HOME/.asdf/asdf.sh' >> $HOME/.bashrc && \
+    echo -e '\n. $HOME/.asdf/asdf.sh' >> $HOME/.profile && \
     source ~/.bashrc
 
 CMD /app/scripts/entrypoint-test.sh
diff --git a/scripts/entrypoint-test.sh b/scripts/entrypoint-test.sh
index 49454ac..e02c93e 100755
--- a/scripts/entrypoint-test.sh
+++ b/scripts/entrypoint-test.sh
@@ -2,10 +2,10 @@
 
 set -eu
 
-source $HOME/.asdf/asdf.sh
+source ${HOME}/.asdf/asdf.sh
 
-asdf install crystal 1.0.0
-asdf global crystal 1.0.0
+asdf install crystal ${CRYSTAL_VERSION}
+asdf global crystal ${CRYSTAL_VERSION}
 
 if [ -z ${GITHUB_ACTION+x} ]
 then
@@ -16,9 +16,6 @@ then
   crystal lib/ameba/bin/ameba.cr
 fi
 
-export CRYSTAL_PATH=lib:/usr/share/crystal/src
-export CRYSTAL_LIBRARY_PATH=/usr/local/lib
-
 watch="false"
 multithreaded="false"
 while [[ $# -gt 0 ]]
@@ -36,13 +33,13 @@ do
   esac
 done
 
-if [[ "$multithreaded" == "true" ]]; then
+if [[ "${multithreaded}" == "true" ]]; then
   args="-Dpreview_mt"
 else
   args=""
 fi
 
-if [[ "$watch" == "true" ]]; then
+if [[ "${watch}" == "true" ]]; then
   CRYSTAL_WORKERS=$(nproc) watchexec -e cr -c -r -w src -w spec -- scripts/crystal-spec.sh -v ${args}
 else
   CRYSTAL_WORKERS=$(nproc) scripts/crystal-spec.sh -v ${args}