diff --git a/.travis.yml b/.travis.yml
index 40b5b50bdb3..894ffe8c5c9 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -87,6 +87,61 @@ jobs:
     services:
     - docker
     stage: Bootstrap Pants
+  - addons:
+      apt:
+        packages:
+        - lib32stdc++6
+        - lib32z1
+        - lib32z1-dev
+        - gcc-multilib
+        - python-dev
+        - openssl
+        - libssl-dev
+        - jq
+        - unzip
+        - shellcheck
+    after_failure:
+    - ./build-support/bin/ci-failure.sh
+    before_cache:
+    - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
+    - find build-support -name "*.py[co]" -delete
+    - ./build-support/bin/prune_travis_cache.sh
+    before_install:
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - pyenv global 2.7.17 3.6.10 3.7.6 3.8.1
+    cache:
+      directories:
+      - ${AWS_CLI_ROOT}
+      - ${PYENV_ROOT_OSX}
+      - ${HOME}/.rustup
+      - ${HOME}/.cargo
+      - build-support/virtualenvs
+      - src/rust/engine/target
+      timeout: 500
+    dist: bionic
+    env:
+    - CACHE_NAME=bootstrap.linux.py38
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.linux
+    language: python
+    name: Build Linux native engine and pants.pex (Python 3.8)
+    os: linux
+    python:
+    - '2.7'
+    - '3.6'
+    - '3.7'
+    script:
+    - docker build --rm -t travis_ci --build-arg "TRAVIS_USER=$(id -un)" --build-arg
+      "TRAVIS_UID=$(id -u)" --build-arg "TRAVIS_GROUP=$(id -gn)" --build-arg "TRAVIS_GID=$(id
+      -g)" build-support/docker/travis_ci/
+    - docker run --rm -t -v "${HOME}:/travis/home" -v "${TRAVIS_BUILD_DIR}:/travis/workdir"
+      travis_ci:latest sh -c "curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs
+      | sh -s -- -y --default-toolchain none && source /travis/home/.cargo/env &&
+      ./build-support/bin/bootstrap_and_deploy_ci_pants_pex.py --python-version 3.8
+      --aws-bucket ${AWS_BUCKET} --native-engine-so-key-prefix ${NATIVE_ENGINE_SO_KEY_PREFIX}
+      --pex-key ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}"
+    services:
+    - docker
+    stage: Bootstrap Pants (Cron)
   - after_failure:
     - ./build-support/bin/ci-failure.sh
     before_cache:
@@ -131,6 +186,50 @@ jobs:
       --aws-bucket ${AWS_BUCKET} --native-engine-so-key-prefix ${NATIVE_ENGINE_SO_KEY_PREFIX}
       --pex-key ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
     stage: Bootstrap Pants
+  - after_failure:
+    - ./build-support/bin/ci-failure.sh
+    before_cache:
+    - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
+    - find build-support -name "*.py[co]" -delete
+    - ./build-support/bin/prune_travis_cache.sh
+    before_install:
+    - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
+      -o /usr/local/bin/jq
+    - chmod 755 /usr/local/bin/jq
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - ./build-support/bin/install_python_for_ci.sh ${MACOS_PYENV_PY27_VERSION} ${MACOS_PYENV_PY38_VERSION}
+    before_script:
+    - ulimit -n 8192
+    cache:
+      directories:
+      - ${AWS_CLI_ROOT}
+      - ${PYENV_ROOT_OSX}
+      - ${HOME}/.rustup
+      - ${HOME}/.cargo
+      - build-support/virtualenvs
+      - src/rust/engine/target
+      timeout: 500
+    env:
+    - PATH="/usr/local/opt/openssl/bin:${PATH}"
+    - LDFLAGS="-L/usr/local/opt/openssl/lib"
+    - CPPFLAGS="-I/usr/local/opt/openssl/include"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY27_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY37_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY38_VERSION}/bin:${PATH}"
+    - CACHE_NAME=bootstrap.osx.py38
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.osx
+    language: generic
+    name: Build macOS native engine and pants.pex (Python 3.8)
+    os: osx
+    osx_image: xcode8
+    script:
+    - curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s -- -y --default-toolchain
+      none
+    - source ${HOME}/.cargo/env
+    - ./build-support/bin/bootstrap_and_deploy_ci_pants_pex.py --python-version 3.8
+      --aws-bucket ${AWS_BUCKET} --native-engine-so-key-prefix ${NATIVE_ENGINE_SO_KEY_PREFIX}
+      --pex-key ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    stage: Bootstrap Pants (Cron)
   - addons:
       apt:
         packages:
@@ -183,6 +282,58 @@ jobs:
     - travis-wait-enhanced --timeout 50m --interval 9m -- ./build-support/bin/ci.py
       --githooks --smoke-tests --lint --python-version 3.7
     stage: Test Pants
+  - addons:
+      apt:
+        packages:
+        - lib32stdc++6
+        - lib32z1
+        - lib32z1-dev
+        - gcc-multilib
+        - python-dev
+        - openssl
+        - libssl-dev
+        - jq
+        - unzip
+        - shellcheck
+    after_failure:
+    - ./build-support/bin/ci-failure.sh
+    before_cache:
+    - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
+    - rm -rf "${HOME}/.cargo/registry/src"
+    - du -m -d2 ${HOME}/.cache/pants | sort -r -n
+    - ./build-support/bin/prune_travis_cache.sh
+    before_install:
+    - sudo sysctl fs.inotify.max_user_watches=524288
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - pyenv global 2.7.17 3.6.10 3.7.6 3.8.1
+    - wget -qO- "https://github.com/crazy-max/travis-wait-enhanced/releases/download/v0.2.1/travis-wait-enhanced_0.2.1_linux_x86_64.tar.gz"
+      | tar -zxvf - travis-wait-enhanced
+    - mv travis-wait-enhanced /home/travis/bin/
+    before_script:
+    - ./build-support/bin/get_ci_bootstrapped_pants_pex.sh ${AWS_BUCKET} ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    cache:
+      directories:
+      - ${AWS_CLI_ROOT}
+      - ${PYENV_ROOT_OSX}
+      timeout: 500
+    dist: bionic
+    env:
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.linux
+    - CACHE_NAME=lint.py38
+    language: python
+    name: Self-checks and lint (Python 3.8)
+    os: linux
+    python:
+    - '2.7'
+    - '3.6'
+    - '3.7'
+    script:
+    - curl --proto '=https' --tlsv1.2 -sSf https://sh.rustup.rs | sh -s -- -y --default-toolchain
+      none
+    - source ${HOME}/.cargo/env
+    - travis-wait-enhanced --timeout 50m --interval 9m -- ./build-support/bin/ci.py
+      --githooks --smoke-tests --lint --python-version 3.8
+    stage: Test Pants (Cron)
   - before_cache:
     - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
     - find build-support -name "*.py[co]" -delete
@@ -303,6 +454,57 @@ jobs:
     - travis-wait-enhanced --timeout 65m --interval 9m -- ./build-support/bin/ci.py
       --unit-tests --integration-tests --python-version 3.7
     stage: Test Pants
+  - addons:
+      apt:
+        packages:
+        - lib32stdc++6
+        - lib32z1
+        - lib32z1-dev
+        - gcc-multilib
+        - python-dev
+        - openssl
+        - libssl-dev
+        - jq
+        - unzip
+        - shellcheck
+    after_failure:
+    - ./build-support/bin/ci-failure.sh
+    after_success:
+    - ./build-support/bin/upload_coverage.sh
+    before_cache:
+    - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
+    - rm -rf "${HOME}/.cargo/registry/src"
+    - du -m -d2 ${HOME}/.cache/pants | sort -r -n
+    - ./build-support/bin/prune_travis_cache.sh
+    before_install:
+    - sudo sysctl fs.inotify.max_user_watches=524288
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - pyenv global 2.7.17 3.6.10 3.7.6 3.8.1
+    - wget -qO- "https://github.com/crazy-max/travis-wait-enhanced/releases/download/v0.2.1/travis-wait-enhanced_0.2.1_linux_x86_64.tar.gz"
+      | tar -zxvf - travis-wait-enhanced
+    - mv travis-wait-enhanced /home/travis/bin/
+    before_script:
+    - ./build-support/bin/get_ci_bootstrapped_pants_pex.sh ${AWS_BUCKET} ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    cache:
+      directories:
+      - ${AWS_CLI_ROOT}
+      - ${PYENV_ROOT_OSX}
+      timeout: 500
+    dist: bionic
+    env:
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.linux
+    - CACHE_NAME=python_tests.py38
+    language: python
+    name: Python tests (Python 3.8)
+    os: linux
+    python:
+    - '2.7'
+    - '3.6'
+    - '3.7'
+    script:
+    - travis-wait-enhanced --timeout 65m --interval 9m -- ./build-support/bin/ci.py
+      --unit-tests --integration-tests --python-version 3.8
+    stage: Test Pants (Cron)
   - before_cache:
     - sudo chown -R travis:travis "${HOME}" "${TRAVIS_BUILD_DIR}"
     - find build-support -name "*.py[co]" -delete
@@ -503,6 +705,30 @@ jobs:
     script:
     - ./build-support/bin/ci.py --platform-specific-tests --python-version 3.7
     stage: Test Pants
+  - before_install:
+    - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
+      -o /usr/local/bin/jq
+    - chmod 755 /usr/local/bin/jq
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - ./build-support/bin/install_python_for_ci.sh ${MACOS_PYENV_PY27_VERSION} ${MACOS_PYENV_PY38_VERSION}
+    before_script:
+    - ulimit -n 8192
+    - ./build-support/bin/get_ci_bootstrapped_pants_pex.sh ${AWS_BUCKET} ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    env:
+    - PATH="/usr/local/opt/openssl/bin:${PATH}"
+    - LDFLAGS="-L/usr/local/opt/openssl/lib"
+    - CPPFLAGS="-I/usr/local/opt/openssl/include"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY27_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY37_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY38_VERSION}/bin:${PATH}"
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.osx
+    - CACHE_NAME=osx_platform_tests.py38
+    language: generic
+    name: macOS platform-specific tests (Python 3.8)
+    os: osx
+    script:
+    - ./build-support/bin/ci.py --platform-specific-tests --python-version 3.8
+    stage: Test Pants (Cron)
   - before_install:
     - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
       -o /usr/local/bin/jq
@@ -528,6 +754,31 @@ jobs:
     script:
     - MODE=debug ./build-support/bin/ci.py --smoke-tests --python-version 3.7
     stage: Test Pants
+  - before_install:
+    - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
+      -o /usr/local/bin/jq
+    - chmod 755 /usr/local/bin/jq
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - ./build-support/bin/install_python_for_ci.sh ${MACOS_PYENV_PY27_VERSION} ${MACOS_PYENV_PY38_VERSION}
+    before_script:
+    - ulimit -n 8192
+    - ./build-support/bin/get_ci_bootstrapped_pants_pex.sh ${AWS_BUCKET} ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    env:
+    - PATH="/usr/local/opt/openssl/bin:${PATH}"
+    - LDFLAGS="-L/usr/local/opt/openssl/lib"
+    - CPPFLAGS="-I/usr/local/opt/openssl/include"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY27_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY37_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY38_VERSION}/bin:${PATH}"
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.osx
+    - CACHE_NAME=osx_smoke_tests.10_12.py38
+    language: generic
+    name: macOS 10.12 smoke test (Python 3.8)
+    os: osx
+    osx_image: xcode9.2
+    script:
+    - MODE=debug ./build-support/bin/ci.py --smoke-tests --python-version 3.8
+    stage: Test Pants (Cron)
   - before_install:
     - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
       -o /usr/local/bin/jq
@@ -553,6 +804,31 @@ jobs:
     script:
     - MODE=debug ./build-support/bin/ci.py --smoke-tests --python-version 3.7
     stage: Test Pants
+  - before_install:
+    - curl -L https://github.com/stedolan/jq/releases/download/jq-1.5/jq-osx-amd64
+      -o /usr/local/bin/jq
+    - chmod 755 /usr/local/bin/jq
+    - ./build-support/bin/install_aws_cli_for_ci.sh
+    - ./build-support/bin/install_python_for_ci.sh ${MACOS_PYENV_PY27_VERSION} ${MACOS_PYENV_PY38_VERSION}
+    before_script:
+    - ulimit -n 8192
+    - ./build-support/bin/get_ci_bootstrapped_pants_pex.sh ${AWS_BUCKET} ${BOOTSTRAPPED_PEX_KEY_PREFIX}.${BOOTSTRAPPED_PEX_KEY_SUFFIX}
+    env:
+    - PATH="/usr/local/opt/openssl/bin:${PATH}"
+    - LDFLAGS="-L/usr/local/opt/openssl/lib"
+    - CPPFLAGS="-I/usr/local/opt/openssl/include"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY27_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY37_VERSION}/bin:${PATH}"
+    - PATH="${PYENV_ROOT}/versions/${MACOS_PYENV_PY38_VERSION}/bin:${PATH}"
+    - BOOTSTRAPPED_PEX_KEY_SUFFIX=py38.osx
+    - CACHE_NAME=osx_smoke_tests.10_13.py38
+    language: generic
+    name: macOS 10.13 smoke test (Python 3.8)
+    os: osx
+    osx_image: xcode10.1
+    script:
+    - MODE=debug ./build-support/bin/ci.py --smoke-tests --python-version 3.8
+    stage: Test Pants (Cron)
   - addons:
       apt:
         packages:
diff --git a/build-support/bin/ci.py b/build-support/bin/ci.py
index 4a38d6f63bc..9bb4bfe9984 100755
--- a/build-support/bin/ci.py
+++ b/build-support/bin/ci.py
@@ -59,6 +59,7 @@ def main() -> None:
 
 class PythonVersion(Enum):
     py37 = "3.7"
+    py38 = "3.8"
 
     def __str__(self) -> str:
         return str(self.value)
diff --git a/build-support/bin/generate_travis_yml.py b/build-support/bin/generate_travis_yml.py
index dee9933fc5e..64ea894594e 100644
--- a/build-support/bin/generate_travis_yml.py
+++ b/build-support/bin/generate_travis_yml.py
@@ -779,7 +779,7 @@ def ignore_aliases(self, data):
 
 
 def main() -> None:
-    supported_python_versions = [PythonVersion.py37]
+    supported_python_versions = [PythonVersion.py37, PythonVersion.py38]
     generated_yaml = yaml.dump(
         {
             # Conditions are documented here: https://docs.travis-ci.com/user/conditions-v1
diff --git a/src/python/pants/util/objects_test.py b/src/python/pants/util/objects_test.py
index fac44474381..9f775fc0498 100644
--- a/src/python/pants/util/objects_test.py
+++ b/src/python/pants/util/objects_test.py
@@ -150,7 +150,9 @@ class FallbackToObject:
         get_docstring(FallbackToObject, fallback_to_ancestors=True, ignored_ancestors=[object])
         is None
     )
+    object_docstring = object.__doc__
+    assert object_docstring is not None
     assert (
         get_docstring(FallbackToObject, fallback_to_ancestors=True, ignored_ancestors=[])
-        == object.__doc__
+        == object_docstring.rstrip()
     )