diff --git a/.github/scripts/setup-env.sh b/.github/scripts/setup-env.sh
new file mode 100755
index 0000000..1b43d94
--- /dev/null
+++ b/.github/scripts/setup-env.sh
@@ -0,0 +1,72 @@
+#!/usr/bin/env bash
+#
+# Environment setup script for the local project. Intended to be used with automation
+# to create a repeatable local environment for tests to be run in. The python env
+# this script creates can be accessed at the location defined by the CI_VENV variable
+# below.
+
+set -e;
+
+# ##### Prereqs #####
+#
+# Set global vars for usage in the script, create the cache directory so we can rely
+# on that existing, then dump some diagnostic info for later reference.
+#
+CI_VENV=$HOME/ci;
+CI_CACHE=$HOME/.cache;
+CI_CACHE_GET_POETRY="$CI_CACHE/get-poetry.py";
+CI_POETRY=$HOME/.poetry/bin/poetry;
+CI_VENV_PIP="$CI_VENV/bin/pip";
+CI_VENV_PIP_VERSION=19.3.1;
+CI_VENV_TOX="$CI_VENV/bin/tox";
+
+mkdir --parents "$CI_CACHE";
+
+command -v python;
+python --version;
+
+# ##### Install Poetry #####
+#
+# Download the poetry install script to the cache directory and then install poetry.
+# After dump the poetry version for later reference.
+#
+curl https://raw.githubusercontent.com/python-poetry/poetry/master/get-poetry.py \
+  --output "$CI_CACHE_GET_POETRY" \
+  --silent \
+  --show-error \
+  --location;
+python "$CI_CACHE_GET_POETRY" --yes 1>/dev/null;
+
+python "$CI_POETRY" --version --no-ansi;
+
+# ##### Setup Runtime Venv #####
+#
+# Create a virtual environment for poetry to use, upgrade pip in that venv to a pinned
+# version, then install the current project to the venv.
+#
+# Note 1: Poetry, Tox, and this project plugin all use pip under the hood for package
+#         installation. This means that even though we are creating up to eight venvs
+#         during a given CI run they all share the same download cache.
+# Note 2: The "VIRTUAL_ENV=$CI_VENV" prefix on the poetry commands below sets the venv
+#         that poetry will use for operations. There is no CLI flag for poetry that
+#         directs it to use a given environment, but if it finds itself in an existing
+#         environment it will use it and skip environment creation.
+#
+python -m venv "$CI_VENV";
+
+$CI_VENV_PIP install "pip==$CI_VENV_PIP_VERSION" \
+  --upgrade \
+  --quiet;
+
+VIRTUAL_ENV=$CI_VENV "$CI_POETRY" install \
+  --extras poetry \
+  --quiet \
+  --no-ansi \
+  &>/dev/null;
+
+# ##### Print Debug Info #####
+#
+# Print the pip and tox versions (which will include registered plugins)
+#
+$CI_VENV_PIP --version;
+echo "tox $($CI_VENV_TOX --version)";
diff --git a/.github/workflows/ci.yaml b/.github/workflows/ci.yaml
index 6fa8c21..30c31b8 100644
--- a/.github/workflows/ci.yaml
+++ b/.github/workflows/ci.yaml
@@ -20,24 +20,51 @@ jobs:
           - version: 3.9
             toxenv: py39
     steps:
-      - uses: actions/checkout@v2
-      - name: Set up Python ${{ matrix.python.version }}
+      - name: Checkout
+        uses: actions/checkout@v2
+      - name: Setup:python${{ matrix.python.version }}
         uses: actions/setup-python@v1
         with:
           python-version: ${{ matrix.python.version }}
-      - name: Install project
-        run: pip install .
-      - name: Run tests via ${{ matrix.python.toxenv }}
-        run: tox -e ${{ matrix.python.toxenv }}
+      - name: Setup:cache
+        uses: actions/cache@v2
+        with:
+          path: |
+            ~/.cache/pip
+            ~/.cache/pypoetry/cache
+            ~/.poetry
+          # Including the hashed poetry.lock in the cache slug ensures that the cache
+          # will be invalidated, and thus all packages will be redownloaded, if the
+          # lockfile is updated
+          key: ${{ runner.os }}-${{ matrix.python.toxenv }}-${{ hashFiles('**/poetry.lock') }}
+      - name: Setup:env
+        run: .github/scripts/setup-env.sh
+      - name: Run:${{ matrix.python.toxenv }}
+        run: $HOME/ci/bin/tox -e ${{ matrix.python.toxenv }}
   Check:
     runs-on: ubuntu-latest
     steps:
-      - uses: actions/checkout@v2
-      - name: Set up Python 3.8
+      - name: Checkout
+        uses: actions/checkout@v2
+      - name: Setup:python3.8
         uses: actions/setup-python@v1
         with:
           python-version: 3.8
-      - name: Install project
-        run: pip install .
-      - name: Run meta checks
-        run: tox -e static -e static-tests -e security
+      - name: Setup:cache
+        uses: actions/cache@v2
+        with:
+          path: |
+            ~/.cache/pip
+            ~/.cache/pypoetry/cache
+            ~/.poetry
+          # Hardcoded 'py38' slug here lets this cache piggyback on the 'py38' cache
+          # that is generated for the tests above
+          key: ${{ runner.os }}-py38-${{ hashFiles('**/poetry.lock') }}
+      - name: Setup:env
+        run: .github/scripts/setup-env.sh
+      - name: Run:static
+        run: $HOME/ci/bin/tox -e static
+      - name: Run:static-tests
+        run: $HOME/ci/bin/tox -e static-tests
+      - name: Run:security
+        run: $HOME/ci/bin/tox -e security