diff --git a/.ci/build.sh b/.ci/build.sh
new file mode 100755
index 000000000..d259356ec
--- /dev/null
+++ b/.ci/build.sh
@@ -0,0 +1,20 @@
+#!/usr/bin/env bash
+
+csource="${BASH_SOURCE[0]}"
+while [ -h "$csource" ] ; do csource="$(readlink "$csource")"; done
+root="$( cd -P "$( dirname "$csource" )/../" && pwd )"
+
+. "${root}/.ci/common.sh"
+
+pushd "${root}" > "${output}"
+
+# Build our gem
+wrap gem build *.gemspec \
+     "Failed to build Vagrant RubyGem"
+
+# Get the path of our new gem
+g=(vagrant*.gem)
+gem=$(printf "%s" "${g}")
+
+wrap aws s3 cp "${gem}" "${ASSETS_PRIVATE_BUCKET}/${repository}/vagrant-master.gem" \
+     "Failed to store Vagrant RubyGem master build"
diff --git a/.ci/common.sh b/.ci/common.sh
new file mode 100644
index 000000000..7d33a0057
--- /dev/null
+++ b/.ci/common.sh
@@ -0,0 +1,358 @@
+#!/usr/bin/env bash
+
+# Write failure message, send error to configured
+# slack, and exit with non-zero status. If a
+# /tmp/.ci-output file exists, the last 5 lines will be
+# included in the slack message.
+#
+# $1: Failure message
+function fail() {
+    (>&2 echo "ERROR: ${1}")
+    if [ -f "/tmp/.ci-output" ]; then
+        slack -s error -m "ERROR: ${1}" -f /tmp/.ci-output -T 5
+    else
+        slack -s error -m "ERROR: ${1}"
+    fi
+    exit 1
+}
+
+# Write warning message, send warning to configured
+# slack
+#
+# $1: Warning message
+function warn() {
+    (>&2 echo "WARN:  ${1}")
+    if [ -f "/tmp/.ci-output" ]; then
+        slack -s warn -m "WARNING: ${1}" -f /tmp/.ci-output
+    else
+        slack -s warn -m "WARNING: ${1}"
+    fi
+}
+
+# Execute command while redirecting all output to
+# a file (file is used within fail mesage on when
+# command is unsuccessful). Final argument is the
+# error message used when the command fails.
+#
+# $@{1:$#-1}: Command to execute
+# $@{$#}: Failure message
+function wrap() {
+    i=$(("${#}" - 1))
+    rm -f /tmp/.ci-output
+    "${@:1:$i}" > /tmp/.ci-output 2>&1
+    if [ $? -ne 0 ]; then
+        cat /tmp/.ci-output
+        fail "${@:$#}"
+    fi
+    rm /tmp/.ci-output
+}
+
+# Execute command while redirecting all output to
+# a file (file is used within fail mesage on when
+# command is unsuccessful). Command output will be
+# streamed during execution. Final argument is the
+# error message used when the command fails.
+#
+# $@{1:$#-1}: Command to execute
+# $@{$#}: Failure message
+function wrap_stream() {
+    i=$(("${#}" - 1))
+    rm -f /tmp/.ci-output
+    "${@:1:$i}" > /tmp/.ci-output 2>&1 &
+    pid=$!
+    until [ -f /tmp/.ci-output ]; do
+        sleep 0.1
+    done
+    tail -f --quiet --pid "${pid}" /tmp/.ci-output
+    wait "${pid}"
+    if [ $? -ne 0 ]; then
+        fail "${@:$#}"
+    fi
+    rm /tmp/.ci-output
+}
+
+# Send command to packet device and wrap
+# execution
+function pkt_wrap() {
+    wrap packet-exec run -quiet -- "${@}"
+}
+
+# Send command to packet device and wrap
+# execution with output streaming
+function pkt_wrap_stream() {
+    wrap_stream packet-exec run -quiet -- "${@}"
+}
+
+# Generates location within the asset storage
+# bucket to retain built assets.
+function asset_location() {
+    if [ "${tag}" = "" ]; then
+        dst="${ASSETS_PRIVATE_LONGTERM}/${repository}/${ident_ref}/${short_sha}"
+    else
+        if [[ "${tag}" = *"+"* ]]; then
+            dst="${ASSETS_PRIVATE_LONGTERM}/${repository}/${tag}"
+        else
+            dst="${ASSETS_PRIVATE_BUCKET}/${repository}/${tag}"
+        fi
+    fi
+    echo -n "${dst}"
+}
+
+# Upload assets to the asset storage bucket.
+#
+# $1: Path to asset file or directory to upload
+function upload_assets() {
+    if [ "${1}" = "" ]; then
+        fail "Parameter required for asset upload"
+    fi
+    if [ -d "${1}" ]; then
+        wrap aws s3 cp --recursive "${1}" "$(asset_location)/" \
+             "Upload to asset storage failed"
+    else
+        wrap aws s3 cp "${1}" "$(asset_location)/" \
+             "Upload to asset storage failed"
+    fi
+}
+
+# Download assets from the asset storage bucket. If
+# destination is not provided, remote path will be
+# used locally.
+#
+# $1: Path to asset or directory to download
+# $2: Optional destination for downloaded assets
+function download_assets() {
+    if [ "${1}" = "" ]; then
+        fail "At least one parameter required for asset download"
+    fi
+    if [ "${2}" = "" ]; then
+        dst="${1#/}"
+    else
+        dst="${2}"
+    fi
+    mkdir -p "${dst}"
+    src="$(asset_location)/${1#/}"
+    remote=$(aws s3 ls "${src}")
+    if [[ "${remote}" = *" PRE "* ]]; then
+        mkdir -p "${dst}"
+        wrap aws s3 cp --recursive "${src%/}/" "${dst}" \
+             "Download from asset storage failed"
+    else
+        mkdir -p "$(dirname "${dst}")"
+        wrap aws s3 cp "${src}" "${dst}" \
+             "Download from asset storage failed"
+    fi
+}
+
+# Upload assets to the cache storage bucket.
+#
+# $1: Path to asset file or directory to upload
+function upload_cache() {
+    if [ "${1}" = "" ]; then
+        fail "Parameter required for cache upload"
+    fi
+    if [ -d "${1}" ]; then
+        wrap aws s3 cp --recursive "${1}" "${asset_cache}/" \
+             "Upload to cache failed"
+    else
+        wrap aws s3 cp "${1}" "${asset_cache}/" \
+             "Upload to cache failed"
+    fi
+}
+
+# Download assets from the cache storage bucket. If
+# destination is not provided, remote path will be
+# used locally.
+#
+# $1: Path to asset or directory to download
+# $2: Optional destination for downloaded assets
+function download_cache() {
+    if [ "${1}" = "" ]; then
+        fail "At least one parameter required for cache download"
+    fi
+    if [ "${2}" = "" ]; then
+        dst="${1#/}"
+    else
+        dst="${2}"
+    fi
+    mkdir -p "${dst}"
+    src="${asset_cache}/${1#/}"
+    remote=$(aws s3 ls "${src}")
+    if [[ "${remote}" = *" PRE "* ]]; then
+        mkdir -p "${dst}"
+        wrap aws s3 cp --recursive "${src%/}/" "${dst}" \
+             "Download from cache storage failed"
+    else
+        mkdir -p "$(dirname "${dst}")"
+        wrap aws s3 cp "${src}" "${dst}" \
+             "Download from cache storage failed"
+    fi
+}
+
+# Validate arguments for GitHub release. Checks for
+# two arguments and that second argument is an exiting
+# file asset, or directory.
+#
+# $1: GitHub tag name
+# $2: Asset file or directory of assets
+function release_validate() {
+    if [ "${1}" = "" ]; then
+        fail "Missing required position 1 argument (TAG) for release"
+    fi
+    if [ "${2}" = "" ]; then
+        fail "Missing required position 2 argument (PATH) for release"
+    fi
+    if [ ! -e "${2}" ]; then
+        fail "Path provided for release (${2}) does not exist"
+    fi
+}
+
+# Generate a GitHub release
+#
+# $1: GitHub tag name
+# $2: Asset file or directory of assets
+function release() {
+    release_validate "${@}"
+    wrap ghr -u "${repo_owner}" -r "${repo_name}" -c "${full_sha}" -n "${1}" -delete \
+         -replace "${1}" "${2}" "Failed to create release for version ${1}"
+}
+
+# Generate a GitHub prerelease
+#
+# $1: GitHub tag name
+# $2: Asset file or directory of assets
+function prerelease() {
+    release_validate "${@}"
+    if [[ "${1}" != *"+"* ]]; then
+        ptag="${1}+${short_sha}"
+    else
+        ptag="${1}"
+    fi
+
+    wrap ghr -u "${repo_owner}" -r "${repo_name}" -c "${full_sha}" -n "${ptag}" \
+         -delete -replace -prerelease "${ptag}" "${2}" \
+         "Failed to create prerelease for version ${1}"
+    echo -n "${ptag}"
+}
+
+# Check if version string is valid for release
+#
+# $1: Version
+# Returns: 0 if valid, 1 if invalid
+function valid_release_version() {
+    if [[ "${1}" =~ ^v[0-9]+\.[0-9]+\.[0-9]+$ ]]; then
+        return 0
+    else
+        return 1
+    fi
+}
+
+# Validate arguments for HashiCorp release. Ensures asset
+# directory exists, and checks that the SHASUMS and SHASUM.sig
+# files are present.
+#
+# $1: Asset directory
+function hashicorp_release_validate() {
+    directory="${1}"
+
+    # Directory checks
+    if [ "${directory}" = "" ]; then
+        fail "No asset directory was provided for HashiCorp release"
+    fi
+    if [ ! -d "${directory}" ]; then
+        fail "Asset directory for HashiCorp release does not exist"
+    fi
+
+    # SHASUMS checks
+    if [ ! -e "${directory}/"*SHASUMS ]; then
+        fail "Asset directory is missing SHASUMS file"
+    fi
+    if [ ! -e "${directory}/"*SHASUMS.sig ]; then
+        fail "Asset directory is missing SHASUMS signature file"
+    fi
+}
+
+# Verify release assets by validating checksum properly match
+# and that signature file is valid
+#
+# $1: Asset directory
+function hashicorp_release_verify() {
+    directory="${1}"
+    pushd "${directory}" > "${output}"
+
+    # First do a checksum validation
+    wrap shasum -a 256 -c *_SHA256SUMS \
+         "Checksum validation of release assets failed"
+    # Next check that the signature is valid
+    gpghome=$(mktemp -qd)
+    export GNUPGHOME="${gpghome}"
+    wrap gpg --import "${HASHICORP_PUBLIC_GPG_KEY}" \
+         "Failed to import HashiCorp public GPG key"
+    wrap gpg --verify *SHA256SUMS.sig *SHA256SUMS \
+         "Validation of SHA256SUMS signature failed"
+    rm -rf "${gpghome}" > "${output}" 2>&1
+    popd > "${output}"
+}
+
+# Generate a HashiCorp release
+#
+# $1: Asset directory
+function hashicorp_release() {
+    directory="${1}"
+
+    hashicorp_release_validate "${directory}"
+    hashicorp_release_verify "${directory}"
+
+    wrap_stream hc-releases upload "${directory}" \
+                "Failed to upload HashiCorp release assets"
+    wrap_stream hc-releases publish \
+                "Failed to publish HashiCorp release"
+}
+
+# Stub cleanup method which can be redefined
+# within actual script
+function cleanup() {
+    (>&2 echo "** No cleanup tasks defined")
+}
+
+trap cleanup EXIT
+
+# Enable debugging. This needs to be enabled with
+# extreme caution when used on public repositories.
+# Output with debugging enabled will likely include
+# secret values which should not be publicly exposed.
+#
+# If repository is public, FORCE_PUBLIC_DEBUG environment
+# variable must also be set.
+if [ "${DEBUG}" != "" ]; then
+    is_private=$(curl -s "https://api.github.com/repos/${GITHUB_REPOSITORY}" | jq .private)
+    if [ "${is_private}" = "false" ]; then
+        if [ "${FORCE_PUBLIC_DEBUG}" != "" ]; then
+            set -x
+            output="/dev/stdout"
+        else
+            fail "Cannot enable debug mode on public repository unless forced"
+        fi
+    else
+        set -x
+        output="/dev/stdout"
+    fi
+else
+    output="/dev/null"
+fi
+
+# Common variables
+full_sha="${GITHUB_SHA}"
+short_sha="${full_sha:0:8}"
+ident_ref="${GITHUB_REF#*/*/}"
+if [[ "${GITHUB_REF}" == *"refs/tags/"* ]]; then
+    tag="${GITHUB_REF##*tags/}"
+    valid_release_version "${tag}"
+    if [ $? -eq 0 ]; then
+        release=1
+    fi
+fi
+repository="${GITHUB_REPOSITORY}"
+repo_owner="${repository%/*}"
+repo_name="${repository#*/}"
+asset_cache="${ASSETS_PRIVATE_SHORTTERM}/${repository}/${GITHUB_ACTION}"
+job_id="$(uuidgen)"
diff --git a/.ci/release.sh b/.ci/release.sh
new file mode 100755
index 000000000..f0639fe19
--- /dev/null
+++ b/.ci/release.sh
@@ -0,0 +1,50 @@
+#!/usr/bin/env bash
+
+# NOTE: This release will generate a new release on the installers
+# repository which in turn triggers a full package build
+target_owner="hashicorp"
+target_repository="vagrant-builders"
+
+csource="${BASH_SOURCE[0]}"
+while [ -h "$csource" ] ; do csource="$(readlink "$csource")"; done
+root="$( cd -P "$( dirname "$csource" )/../" && pwd )"
+
+. "${root}/.ci/common.sh"
+
+pushd "${root}" > "${output}"
+
+# Build our gem
+wrap gem build *.gemspec \
+     "Failed to build Vagrant RubyGem"
+
+# Get the path of our new gem
+g=(vagrant*.gem)
+gem=$(printf "%s" "${g}")
+
+# Determine the version of the release
+vagrant_version="$(gem specification "${gem}" version)"
+vagrant_version="${vagrant_version##*version: }"
+
+# We want to release into the builders repository so
+# update the repository variable with the desired destination
+repo_owner="${target_owner}"
+repo_name="${target_repository}"
+export GITHUB_TOKEN="${HASHIBOT_TOKEN}"
+
+if [ "${tag}" = "" ]; then
+    echo "Generating Vagrant RubyGem pre-release... "
+    version="v${vagrant_version}+${short_sha}"
+    prerelease "${version}" "${gem}"
+else
+    # Validate this is a proper release version
+    valid_release_version "${vagrant_version}"
+    if [ $? -ne 0 ]; then
+        fail "Invalid version format for Vagrant release: ${vagrant_version}"
+    fi
+
+    echo "Generating Vagrant RubyGem release... "
+    version="v${vagrant_version}"
+    release "${version}" "${gem}"
+fi
+
+slack -m "New Vagrant installers release triggered: *${version}*"
diff --git a/.ci/test.sh b/.ci/test.sh
new file mode 100755
index 000000000..f7ad3b2a0
--- /dev/null
+++ b/.ci/test.sh
@@ -0,0 +1,27 @@
+#!/usr/bin/env bash
+
+csource="${BASH_SOURCE[0]}"
+while [ -h "$csource" ] ; do csource="$(readlink "$csource")"; done
+root="$( cd -P "$( dirname "$csource" )/../" && pwd )"
+
+pushd "${root}" > /dev/null
+
+export DEBIAN_FRONTEND="noninteractive"
+
+# Install required dependencies
+sudo apt-get update || exit 1
+sudo apt-get install -yq bsdtar || exit 1
+
+# Ensure bundler is installed
+gem install --no-document bundler || exit 1
+
+# Install the bundle
+bundle install || exit 1
+
+# Run tests
+bundle exec rake test:unit
+
+result=$?
+popd > /dev/null
+
+exit $result
diff --git a/.circleci/config.yml b/.circleci/config.yml
index 737ee4c64..61c8342df 100644
--- a/.circleci/config.yml
+++ b/.circleci/config.yml
@@ -1,127 +1,6 @@
 version: 2
-reference:
-  environment: &ENVIRONMENT
-    SLACK_TITLE: Vagrant CI
-    RELEASE_TARGET_REPONAME: vagrant-installers
-  images:
-    ruby24: &ruby24
-      docker:
-        - image: circleci/ruby:2.4
-    ruby25: &ruby25
-      docker:
-        - image: circleci/ruby:2.5
-    ruby26: &ruby26
-      docker:
-        - image: circleci/ruby:2.6
-    builder: &builder
-      environment:
-        <<: *ENVIRONMENT
-      docker:
-        - image: $BUILDER_IMAGE
-          auth:
-            username: $BUILDER_USERNAME
-            password: $BUILDER_PASSWORD
-  workflows:
-    public: &PUBLIC_WORKFLOW
-      filters:
-        branches:
-          only: /^pull\/.*/
-    master: &MASTER_WORKFLOW
-      filters:
-        branches:
-          only: master
-    private_build: &PRIVATE_WORKFLOW_BUILD
-      context: vagrant
-      filters:
-        branches:
-          only:
-            - /^build-.*/
-        tags:
-          only: /.*/
-  jobs:
-    private_failure: &PRIVATE_FAILURE
-      run:
-        name: Failure handler
-        command: |
-          if [ -f .output ]; then
-            slack -m "Vagrant job has failed: *${CIRCLE_JOB}*" -s error -f .output -T 5
-          else
-            slack -m "Vagrant job has failed: *${CIRCLE_JOB}*" -s error
-          fi
-        when: on_fail
-    unit_tests: &unit_tests
-      steps:
-        - run: sudo apt-get update ; sudo apt-get -yq install bsdtar
-        - checkout
-        - restore_cache:
-            key: static-site-gems-v1-{{ checksum "Gemfile.lock" }}
-        - run:
-            command: bundle check || bundle install --path vendor/bundle
-        - save_cache:
-            key: static-site-gems-v1-{{ checksum "Gemfile.lock" }}
-            paths:
-              - ./vendor/bundle
-        - run: bundle exec rake test:unit
+
 jobs:
-  build:
-    <<: *builder
-    steps:
-      - checkout
-      - run: gem build vagrant.gemspec
-      - *PRIVATE_FAILURE
-      - persist_to_workspace:
-          root: .
-          paths:
-            - ./*.gem
-  store:
-    <<: *builder
-    steps:
-      - attach_workspace:
-          at: .
-      - run: |
-          gem_name=(vagrant-*.gem)
-          if [ "${CIRCLE_TAG}" == "" ]; then
-            remote_gem_name="vagrant-master.gem"
-          else
-            remote_gem_name="vagrant.gem"
-          fi
-          if [[ "${CIRCLE_BRANCH}" = "build-"* ]]; then
-            s3_dst="${ASSETS_PRIVATE_LONGTERM}/${CIRCLE_PROJECT_USERNAME}/${CIRCLE_PROJECT_REPONAME}/${CIRCLE_BRANCH##build-}/"
-          else
-            s3_dst="${ASSETS_PRIVATE_BUCKET}/${CIRCLE_PROJECT_USERNAME}/${CIRCLE_PROJECT_REPONAME}/"
-          fi
-          aws s3 cp "${gem_name}" "${s3_dst}${remote_gem_name}" > .output 2>&1
-      - *PRIVATE_FAILURE
-  release:
-    <<: *builder
-    steps:
-      - checkout
-      - attach_workspace:
-          at: .
-      - run: |
-          set +e
-          gem=(vagrant-*.gem)
-          gem_version="${gem##vagrant-}"
-          gem_version="${gem_version%%.gem}"
-          export GITHUB_TOKEN="${HASHIBOT_TOKEN}"
-          if [ "${CIRCLE_TAG}" = "" ]; then
-            version="v${gem_version}+$(git rev-parse --short "${CIRCLE_SHA1}")"
-            ghr -u ${CIRCLE_PROJECT_USERNAME} -r ${RELEASE_TARGET_REPONAME} -c master -prerelease -delete -replace ${version} ${gem} > .output 2>&1
-          else
-            version="${CIRCLE_TAG}"
-            ghr -u ${CIRCLE_PROJECT_USERNAME} -r ${RELEASE_TARGET_REPONAME} -c master -delete -replace ${version} ${gem} > .output 2>&1
-          fi
-          slack -m "New Vagrant installers release triggered: *${version}*"
-      - *PRIVATE_FAILURE
-  test_ruby24:
-    <<: *ruby24
-    <<: *unit_tests
-  test_ruby25:
-    <<: *ruby25
-    <<: *unit_tests
-  test_ruby26:
-    <<: *ruby26
-    <<: *unit_tests
   build-website:
     # setting the working_directory along with the checkout path allows us to not have
     # to cd into the website/ directory for commands
@@ -145,41 +24,6 @@ jobs:
           command: ./scripts/deploy.sh
 workflows:
   version: 2
-  builds:
-    jobs:
-      - build:
-          <<: *PRIVATE_WORKFLOW_BUILD
-      - store:
-          <<: *PRIVATE_WORKFLOW_BUILD
-          requires:
-            - build
-      - release:
-          <<: *PRIVATE_WORKFLOW_BUILD
-          requires:
-            - build
-  pull_requests:
-    jobs:
-      - test_ruby24:
-          <<: *PUBLIC_WORKFLOW
-      - test_ruby25:
-          <<: *PUBLIC_WORKFLOW
-      - test_ruby26:
-          <<: *PUBLIC_WORKFLOW
-  master:
-    jobs:
-      - test_ruby24:
-          <<: *MASTER_WORKFLOW
-      - test_ruby25:
-          <<: *MASTER_WORKFLOW
-      - test_ruby26:
-          <<: *MASTER_WORKFLOW
-      - build:
-          <<: *MASTER_WORKFLOW
-          context: vagrant
-          requires:
-            - test_ruby24
-            - test_ruby25
-            - test_ruby26
   website:
     jobs:
       - build-website:
diff --git a/.github/workflows/build.yml b/.github/workflows/build.yml
new file mode 100644
index 000000000..9a2f38adf
--- /dev/null
+++ b/.github/workflows/build.yml
@@ -0,0 +1,21 @@
+on:
+  push:
+    branches:
+      - master
+    paths-ignore:
+      - 'CHANGELOG.md'
+      - 'website/**'
+
+jobs:
+  build-gem:
+    name: Build Vagrant RubyGem
+    runs-on: self-hosted
+    steps:
+      - name: Code Checkout
+        uses: actions/checkout@v1
+      - name: Build RubyGem
+        run: ./.ci/build.sh
+        working-directory: ${{github.workspace}}
+      - name: Clean Workspace
+        if: always()
+        run: rm -rf ${{ github.workspace }}
diff --git a/.github/workflows/release.yml b/.github/workflows/release.yml
new file mode 100644
index 000000000..92275c4ea
--- /dev/null
+++ b/.github/workflows/release.yml
@@ -0,0 +1,22 @@
+on:
+  push:
+    branches:
+      - 'build-*'
+    tags: '*'
+    paths-ignore:
+      - 'CHANGELOG.md'
+      - 'website/**'
+
+jobs:
+  trigger-release:
+    name: Trigger Installers Build
+    runs-on: self-hosted
+    steps:
+      - name: Code Checkout
+        uses: actions/checkout@v1
+      - name: Create Builders Release
+        run: ./.ci/release.sh
+        working-directory: ${{github.workspace}}
+      - name: Clean Workspace
+        if: always()
+        run: rm -rf ${{ github.workspace }}
diff --git a/.github/workflows/testing.yml b/.github/workflows/testing.yml
new file mode 100644
index 000000000..ffbde5eea
--- /dev/null
+++ b/.github/workflows/testing.yml
@@ -0,0 +1,30 @@
+on:
+  push:
+    branches:
+      - master
+      - 'test-*'
+      - 'build-*'
+    paths-ignore:
+      - 'CHANGELOG.md'
+      - 'website/**'
+  pull_request:
+    branches:
+      - master
+
+jobs:
+  unit-tests:
+    runs-on: ubuntu-18.04
+    strategy:
+      matrix:
+        ruby: [ '2.4.x', '2.5.x', '2.6.x' ]
+    name: Vagrant unit tests on Ruby ${{ matrix.ruby }}
+    steps:
+      - name: Code Checkout
+        uses: actions/checkout@v1
+      - name: Setup Ruby
+        uses: actions/setup-ruby@v1
+        with:
+          ruby-version: ${{matrix.ruby}}
+          architecture: 'x64'
+      - name: Run Tests
+        run: .ci/test.sh