diff --git a/CODEOWNERS b/CODEOWNERS
index 5deacc6c..2b618c5f 100644
--- a/CODEOWNERS
+++ b/CODEOWNERS
@@ -1,4 +1,4 @@
 # Code owners file.
 # This file controls who is tagged for review for any given pull request.
 
-* @dlorenc @sharifelgamal @tstromberg @donmccasland
+* @jinglundong @donmccasland
diff --git a/build.sh b/build.sh
index 63afa1ab..2083237d 100755
--- a/build.sh
+++ b/build.sh
@@ -24,7 +24,7 @@ test=0 # Should run standard test suite?
 
 local=0 # Should run using local Docker daemon instead of GCR?
 
-os_base=ubuntu16 # Which operating system base to use
+os_base=ubuntu18 # Which operating system base to use
 interpreter=0 # Should build interpreters instead of images
 
 # Note that $gcloud_cmd has spaces in it
@@ -48,7 +48,7 @@ Options:
   --[no]test: Run basic tests (default true if no options set)
   --[no]client_test: Run Google Cloud Client Library tests (default false)
   --[no]local: Build images using local Docker daemon (default false)
-  --os_base: Which OS image to build on top of [debian8, ubuntu16]
+  --os_base: Which OS image to build on top of [debian8, ubuntu16, ubuntu18]
 "
 }
 
@@ -119,6 +119,10 @@ while [ $# -gt 0 ]; do
       os_base=ubuntu16
       shift
       ;;
+    --os_base=ubuntu18)
+      os_base=ubuntu18
+      shift
+      ;;
     --test)
       test=1
       shift
@@ -156,8 +160,13 @@ fi
 # Pick OS image to use as base
 if [ "${os_base}" == "debian8" ]; then
   export OS_BASE_IMAGE="gcr.io/google-appengine/debian8:latest"
-else
+elif [ "${os_base}" == "ubuntu16" ]; then
   export OS_BASE_IMAGE="gcr.io/gcp-runtimes/ubuntu_16_0_4:latest"
+elif [ "${os_base}" == "ubuntu18" ]; then
+  export OS_BASE_IMAGE="gcr.io/gcp-runtimes/ubuntu_18_0_4:latest"
+else
+  echo "Unsupported OS base image: $OS_BASE_IMAGE"
+  exit 1
 fi
 export STAGING_IMAGE="${DOCKER_NAMESPACE}/python:${TAG}"
 echo "Using base image name ${STAGING_IMAGE}"
diff --git a/builder/gen-dockerfile/Dockerfile.in b/builder/gen-dockerfile/Dockerfile.in
index 4f6447eb..92ceaecf 100644
--- a/builder/gen-dockerfile/Dockerfile.in
+++ b/builder/gen-dockerfile/Dockerfile.in
@@ -1,12 +1,14 @@
 FROM ${STAGING_IMAGE}
-LABEL python_version=python3.6
-RUN virtualenv --no-download /env -p python3.6
+LABEL python_version=python3.7
+RUN virtualenv --no-download /env -p python3.7
 
 # Set virtualenv environment variables. This is equivalent to running
 # source /env/bin/activate
 ENV VIRTUAL_ENV /env
 ENV PATH /env/bin:$PATH
 ADD requirements.txt /builder/
+#virtualenv's pip is pegged at version 10.0, removing so
+#newer versions get picked up
 RUN pip install -r /builder/requirements.txt
 ADD . /builder/
 WORKDIR /workspace
diff --git a/python-interpreter-builder/scripts/build-python-3.7.sh b/python-interpreter-builder/scripts/build-python-3.7.sh
index bee33cef..b1b06806 100755
--- a/python-interpreter-builder/scripts/build-python-3.7.sh
+++ b/python-interpreter-builder/scripts/build-python-3.7.sh
@@ -6,14 +6,14 @@ set -x
 # Get the source
 mkdir -p /opt/sources
 cd /opt/sources
-wget --no-verbose https://www.python.org/ftp/python/3.7.7/Python-3.7.7.tgz
+wget --no-verbose https://www.python.org/ftp/python/3.7.9/Python-3.7.9.tgz
 # SHA-256 generated via `shasum -a 256 [file]`
 shasum --check <<EOF
-8c8be91cd2648a1a0c251f04ea0bb4c2a5570feb9c45eaaa2241c785585b475a  Python-3.7.7.tgz
+39b018bc7d8a165e59aa827d9ae45c45901739b0bbb13721e4f973f3521c166a  Python-3.7.9.tgz
 EOF
-tar xzf Python-3.7.7.tgz
+tar xzf Python-3.7.9.tgz
 
-cd Python-3.7.7
+cd Python-3.7.9
 
 # Explanation of flags:
 #
@@ -146,8 +146,8 @@ find "$PREFIX"/lib/python3.7/test \
 
 # Clean-up sources
 cd /opt
-rm /opt/sources/Python-3.7.7.tgz
-rm -r /opt/sources/Python-3.7.7
+rm /opt/sources/Python-3.7.9.tgz
+rm -r /opt/sources/Python-3.7.9
 
 # Archive and copy to persistent external volume
 tar czf /workspace/runtime-image/interpreter-3.7.tar.gz /opt/python3.7
diff --git a/runtime-image/Dockerfile.in b/runtime-image/Dockerfile.in
index dc842d9b..46387705 100644
--- a/runtime-image/Dockerfile.in
+++ b/runtime-image/Dockerfile.in
@@ -9,6 +9,7 @@ ADD scripts /scripts
 # Install Python, pip, and C dev libraries necessary to compile the most popular
 # Python libraries.
 RUN /scripts/install-apt-packages.sh
+RUN curl "https://bootstrap.pypa.io/pip/2.7/get-pip.py" -o "get-pip.py" && python ./get-pip.py && ln -s /usr/local/bin/pip /usr/bin/pip
 
 # Setup locale. This prevents Python 3 IO encoding issues.
 ENV LANG C.UTF-8
diff --git a/runtime-image/resources/apt-packages.txt b/runtime-image/resources/apt-packages.txt
index 287f7abc..7b88f777 100644
--- a/runtime-image/resources/apt-packages.txt
+++ b/runtime-image/resources/apt-packages.txt
@@ -4,7 +4,6 @@ mercurial
 pkg-config
 wget
 # debian-provided interpreters
-python-pip
 python2.7
 python2.7-dev
 # Dependenies for third-party Python packages
diff --git a/runtime-image/resources/requirements-virtualenv.txt b/runtime-image/resources/requirements-virtualenv.txt
index 52bb7da1..25f09c4a 100644
--- a/runtime-image/resources/requirements-virtualenv.txt
+++ b/runtime-image/resources/requirements-virtualenv.txt
@@ -1 +1 @@
-virtualenv==16.0.0
+virtualenv==20.0.31
diff --git a/scripts/deploy_check.sh b/scripts/deploy_check.sh
index 77fccb54..1e2f02c2 100644
--- a/scripts/deploy_check.sh
+++ b/scripts/deploy_check.sh
@@ -12,11 +12,11 @@ fi
 
 cd ${KOKORO_GFILE_DIR}/appengine/integration_tests
 
-sudo /usr/local/bin/pip install --upgrade -r requirements.txt
+sudo -E /usr/local/bin/pip install --upgrade -r requirements.txt
 
 if [ -f ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt ]
 then
-  sudo /usr/local/bin/pip install --upgrade -r ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt
+  sudo -E /usr/local/bin/pip install --upgrade -r ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt
 fi
 
 export DEPLOY_LATENCY_PROJECT='cloud-deploy-latency'
diff --git a/scripts/integration-test.sh b/scripts/integration-test.sh
index 63137b5f..6210e0a1 100644
--- a/scripts/integration-test.sh
+++ b/scripts/integration-test.sh
@@ -7,11 +7,11 @@ source ${KOKORO_GFILE_DIR}/kokoro/common.sh
 
 export GOOGLE_CLOUD_PROJECT=gcp-runtimes
 
-sudo /usr/local/bin/pip install --upgrade -r ${KOKORO_GFILE_DIR}/appengine/integration_tests/requirements.txt
+sudo -E /usr/local/bin/pip install --upgrade -r ${KOKORO_GFILE_DIR}/appengine/integration_tests/requirements.txt
 
 if [ -f ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt ]
 then
-  sudo /usr/local/bin/pip install --upgrade -r ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt
+  sudo -E /usr/local/bin/pip install --upgrade -r ${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}/requirements.txt
 fi
 
 export GOPATH=${KOKORO_GITHUB_DIR}/${SAMPLE_APP_DIRECTORY}
diff --git a/tests/eventlet/requirements.txt b/tests/eventlet/requirements.txt
index 7f8b2468..1e2ea66b 100644
--- a/tests/eventlet/requirements.txt
+++ b/tests/eventlet/requirements.txt
@@ -1,10 +1,10 @@
 click==6.7
 enum-compat==0.0.2
 eventlet==0.24.1
-Flask==1.0.2
+Flask==2.2.5
 greenlet==0.4.14
 gunicorn==19.9.0
 itsdangerous==0.24
 Jinja2==2.10
-MarkupSafe==1.0
-Werkzeug==0.14.1
+MarkupSafe==1.1.1
+Werkzeug==2.2.3
diff --git a/tests/integration/requirements.txt b/tests/integration/requirements.txt
index ea714c20..a0634bee 100644
--- a/tests/integration/requirements.txt
+++ b/tests/integration/requirements.txt
@@ -1,9 +1,9 @@
-Flask==1.1.0
+Flask==2.2.5
 google-cloud-error-reporting==0.32.1
 google-cloud-logging==1.12.1
 google-cloud-monitoring==0.33.0
 gunicorn==19.9.0
-requests==2.22.0
+requests==2.31.0
 retrying==1.3.3
 six==1.12.0
 protobuf>=3.6.0
diff --git a/tests/no-virtualenv/no-virtualenv.yaml b/tests/no-virtualenv/no-virtualenv.yaml
index 19e48df9..4f6c3f48 100644
--- a/tests/no-virtualenv/no-virtualenv.yaml
+++ b/tests/no-virtualenv/no-virtualenv.yaml
@@ -43,7 +43,7 @@ commandTests:
     expectedOutput: ["/usr/local/bin/python3\n"]
   - name: "default python3 version"
     command: ["python3", "--version"]
-    expectedOutput: ["Python 3.7.7\n"]
+    expectedOutput: ["Python 3.7.9\n"]
   - name: "default pip3 installation"
     command: ["which", "pip3"]
     expectedOutput: ["/usr/local/bin/pip3\n"]
diff --git a/tests/python2-libraries/requirements.txt b/tests/python2-libraries/requirements.txt
index 865cd1aa..f0596d67 100644
--- a/tests/python2-libraries/requirements.txt
+++ b/tests/python2-libraries/requirements.txt
@@ -1,7 +1,7 @@
 alembic==1.0.0
 amqp==2.3.2
 amqplib==1.0.2
-ansible==2.6.3
+ansible==7.0.0
 anyjson==0.3.3
 apache-libcloud==2.3.0
 argparse==1.4.0
@@ -20,7 +20,7 @@ botocore==1.11.1
 bottle==0.12.13
 carbon<1.1.1
 celery==4.2.1
-certifi==2018.8.24
+certifi==2023.7.22
 cffi==1.11.5
 chardet==3.0.4
 click==6.7
@@ -53,7 +53,7 @@ extras==1.0.0
 fabric==2.3.1
 fixtures==3.0.0
 flake8==3.5.0
-flask==1.0.2
+flask==2.2.5
 funcsigs==1.0.2
 functools32==3.2.3.post2
 futures==3.2.0
@@ -103,7 +103,7 @@ netaddr==0.7.19
 netifaces==0.10.7
 newrelic==4.2.0.100
 nose==1.3.7
-numpy==1.15.1
+numpy==1.22.0
 oauth2==1.9.0.post1
 oauth2client==4.1.2
 oauthlib==2.1.0
@@ -119,7 +119,7 @@ pbr==4.2.0
 pep8==1.7.1
 pexpect==4.6.0
 pika==0.12.0
-pillow==5.2.0
+pillow==9.3.0
 pip==18.0
 prettytable==0.7.2
 protobuf==3.6.1
@@ -155,16 +155,16 @@ python-novaclient==11.0.0
 python-subunit==1.3.0
 python-swiftclient==3.6.0
 pytz==2018.5
-pyyaml==3.13
+pyyaml==5.4
 pyzmq==17.1.2
 raven==6.9.0
 redis==2.10.6
 repoze.lru==0.7
 requests-oauthlib==1.0.0
-requests==2.19.1
+requests==2.31.0
 retrying==1.3.3
 rsa==3.4.2
-scipy==1.1.0
+scipy==1.10.0
 selenium==3.14.0
 setuptools-git==1.2
 setuptools==40.2.0
@@ -176,7 +176,7 @@ south==1.0.2
 sphinx==1.7.7
 sqlalchemy-migrate==0.11.0
 sqlalchemy==1.2.11
-sqlparse==0.2.4
+sqlparse==0.4.4
 statsd==3.3.0
 stevedore==1.29.0
 suds==0.4
@@ -184,23 +184,23 @@ supervisor==3.3.4
 testrepository==0.0.20
 testtools==2.3.0
 thrift==0.11.0
-tornado==5.1
+tornado==6.3.3
 tox==3.2.1
 twisted==18.7.0
 ujson==1.35
 unidecode==1.0.22
 unittest2==1.1.0
 uritemplate==3.0.0
-urllib3==1.23
-uwsgi==2.0.17.1
+urllib3==1.26.5
+uwsgi==2.0.22
 versiontools==1.9.1
 virtualenv==16.0.0
-waitress==1.1.0
+waitress==2.1.2
 warlock==1.3.0
 webob==1.8.2
 websocket-client==0.51.0
 webtest==2.0.30
-werkzeug==0.14.1
+werkzeug==2.2.3
 wheel==0.31.1
 xlrd==1.1.0
 zc.buildout==2.12.1
diff --git a/tests/python3-libraries/requirements.txt b/tests/python3-libraries/requirements.txt
index e3fd6424..23175a06 100644
--- a/tests/python3-libraries/requirements.txt
+++ b/tests/python3-libraries/requirements.txt
@@ -1,7 +1,7 @@
 alembic==1.0.0
 amqp==2.3.2
 amqplib==1.0.2
-ansible==2.6.3
+ansible==7.0.0
 anyjson==0.3.3
 apache-libcloud==2.3.0
 argparse==1.4.0
@@ -18,7 +18,7 @@ boto==2.49.0
 botocore==1.11.1
 bottle==0.12.13
 celery==4.2.1
-certifi==2018.8.24
+certifi==2023.7.22
 cffi==1.11.5
 chardet==3.0.4
 click==6.7
@@ -30,14 +30,14 @@ cov-core==1.15.0
 coverage==4.5.1
 coveralls==1.4.0
 crcmod==1.7
-cryptography==2.3.1
+cryptography==41.0.3
 cssselect==1.0.3
 cython==0.28.5
 decorator==4.3.0
 django-celery==3.2.2
 django-debug-toolbar==1.9.1
 django-extensions==2.1.1
-django==2.1
+django==2.2.28
 django_compress==1.0.1
 djangorestframework==3.8.2
 docker-py==1.10.6
@@ -51,7 +51,7 @@ extras==1.0.0
 fabric==2.3.1
 fixtures==3.0.0
 flake8==3.5.0
-flask==1.0.2
+flask==2.2.5
 funcsigs==1.0.2
 gevent==1.3.6
 google-api-python-client==1.7.4
@@ -95,7 +95,7 @@ netaddr==0.7.19
 netifaces==0.10.7
 newrelic==4.2.0.100
 nose==1.3.7
-numpy==1.15.1
+numpy==1.22.0
 oauth2==1.9.0.post1
 oauth2client==4.1.2
 oauthlib==2.1.0
@@ -111,7 +111,7 @@ pbr==4.2.0
 pep8==1.7.1
 pexpect==4.6.0
 pika==0.12.0
-pillow==5.2.0
+pillow==9.3.0
 pip==18.0
 prettytable==0.7.2
 protobuf==3.6.1
@@ -123,7 +123,7 @@ pyasn1==0.4.4
 pycparser==2.18
 pycrypto==2.6.1
 pyflakes==2.0.0
-pygments==2.2.0
+pygments==2.15.0
 pyjwt==1.6.4
 pylibmc==1.5.2
 pylint==2.1.1
@@ -145,16 +145,16 @@ python-novaclient==11.0.0
 python-subunit==1.3.0
 python-swiftclient==3.6.0
 pytz==2018.5
-pyyaml==3.13
+pyyaml==5.4
 pyzmq==17.1.2
 raven==6.9.0
 redis==2.10.6
 repoze.lru==0.7
 requests-oauthlib==1.0.0
-requests==2.19.1
+requests==2.31.0
 retrying==1.3.3
 rsa==3.4.2
-scipy==1.1.0
+scipy==1.10.0
 selenium==3.14.0
 setuptools-git==1.2
 setuptools==40.2.0
@@ -166,29 +166,29 @@ south==1.0.2
 sphinx==1.7.7
 sqlalchemy-migrate==0.11.0
 sqlalchemy==1.2.11
-sqlparse==0.2.4
+sqlparse==0.4.4
 statsd==3.3.0
 stevedore==1.29.0
 testrepository==0.0.20
 testtools==2.3.0
 thrift==0.11.0
-tornado==5.1
+tornado==6.3.3
 tox==3.2.1
 twisted==18.7.0
 ujson==1.35
 unidecode==1.0.22
 unittest2==1.1.0
 uritemplate==3.0.0
-urllib3==1.23
-uwsgi==2.0.17.1
+urllib3==1.26.5
+uwsgi==2.0.22
 versiontools==1.9.1
 virtualenv==16.0.0
-waitress==1.1.0
+waitress==2.1.2
 warlock==1.3.0
 webob==1.8.2
 websocket-client==0.51.0
 webtest==2.0.30
-werkzeug==0.14.1
+werkzeug==2.2.3
 wheel==0.31.1
 xlrd==1.1.0
 zc.buildout==2.12.1
diff --git a/tests/virtualenv/virtualenv_default.yaml b/tests/virtualenv/virtualenv_default.yaml
index 1659c746..6b6ad282 100644
--- a/tests/virtualenv/virtualenv_default.yaml
+++ b/tests/virtualenv/virtualenv_default.yaml
@@ -34,4 +34,4 @@ commandTests:
     setup: [["virtualenv", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/local/lib/python2.7/site-packages/flask"]
+    expectedOutput: ["/env/lib/python2.7/site-packages/flask/__init__.pyc"]
diff --git a/tests/virtualenv/virtualenv_python27.yaml b/tests/virtualenv/virtualenv_python27.yaml
index 8bd85289..09b78480 100644
--- a/tests/virtualenv/virtualenv_python27.yaml
+++ b/tests/virtualenv/virtualenv_python27.yaml
@@ -44,4 +44,4 @@ commandTests:
     setup: [["virtualenv", "-p", "python", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/local/lib/python2.7/site-packages/flask"]
+    expectedOutput: ["/env/lib/python2.7/site-packages/flask/__init__.pyc"]
diff --git a/tests/virtualenv/virtualenv_python34.yaml b/tests/virtualenv/virtualenv_python34.yaml
index 077606fa..9b5b77d0 100644
--- a/tests/virtualenv/virtualenv_python34.yaml
+++ b/tests/virtualenv/virtualenv_python34.yaml
@@ -47,7 +47,7 @@ commandTests:
     setup: [["virtualenv", "-p", "python3.4", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/lib/python3.4/site-packages/flask"]
+    expectedOutput: ["/env/lib/python3.4/site-packages/flask/__init__.py"]
 
   - name: "virtualenv34 test.support availability"
     setup: [["virtualenv", "-p", "python3.4", "/env"]]
diff --git a/tests/virtualenv/virtualenv_python35.yaml b/tests/virtualenv/virtualenv_python35.yaml
index 3bb3d814..5e4b394a 100644
--- a/tests/virtualenv/virtualenv_python35.yaml
+++ b/tests/virtualenv/virtualenv_python35.yaml
@@ -47,7 +47,7 @@ commandTests:
     setup: [["virtualenv", "-p", "python3.5", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/lib/python3.5/site-packages/flask"]
+    expectedOutput: ["/env/lib/python3.5/site-packages/flask/__init__.py"]
 
   - name: "virtualenv35 test.support availability"
     setup: [["virtualenv", "-p", "python3.5", "/env"]]
diff --git a/tests/virtualenv/virtualenv_python36.yaml b/tests/virtualenv/virtualenv_python36.yaml
index f0949c6f..b3a9e68e 100644
--- a/tests/virtualenv/virtualenv_python36.yaml
+++ b/tests/virtualenv/virtualenv_python36.yaml
@@ -47,7 +47,7 @@ commandTests:
     setup: [["virtualenv", "-p", "python3.6", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/lib/python3.6/site-packages/flask"]
+    expectedOutput: ["/env/lib/python3.6/site-packages/flask/__init__.py"]
 
   - name: "virtualenv36 test.support availability"
     setup: [["virtualenv", "-p", "python3.6", "/env"]]
diff --git a/tests/virtualenv/virtualenv_python37.yaml b/tests/virtualenv/virtualenv_python37.yaml
index 7de6d10c..9810c78e 100644
--- a/tests/virtualenv/virtualenv_python37.yaml
+++ b/tests/virtualenv/virtualenv_python37.yaml
@@ -25,7 +25,7 @@ commandTests:
   - name: "virtualenv37 python version"
     setup: [["virtualenv", "-p", "python3.7", "/env"]]
     command: ["python", "--version"]
-    expectedOutput: ["Python 3.7.7\n"]
+    expectedOutput: ["Python 3.7.9\n"]
 
   - name: "virtualenv37 pip installation"
     setup: [["virtualenv", "-p", "python3.7", "/env"]]
@@ -47,7 +47,7 @@ commandTests:
     setup: [["virtualenv", "-p", "python3.7", "/env"],
             ["pip", "install", "flask"]]
     command: ["python", "-c", "import flask; print(flask.__file__)"]
-    expectedOutput: ["/env/lib/python3.7/site-packages/flask"]
+    expectedOutput: ["/env/lib/python3.7/site-packages/flask/__init__.py"]
 
   - name: "virtualenv37 test.support availability"
     setup: [["virtualenv", "-p", "python3.7", "/env"]]