diff --git a/.azure-pipelines/jobs/dev-tools.yml b/.azure-pipelines/jobs/dev-tools.yml
new file mode 100644
index 00000000000..549d2ed46c5
--- /dev/null
+++ b/.azure-pipelines/jobs/dev-tools.yml
@@ -0,0 +1,16 @@
+parameters:
+  vmImage:
+
+jobs:
+- job: Developer_Tooling
+  steps:
+  - task: UsePythonVersion@0
+    displayName: Use Python 3 latest
+    inputs:
+      versionSpec: '3'
+
+  - bash: pip install tox
+    displayName: Install dependencies
+
+  - bash: tox -e lint,docs,vendoring
+    displayName: Run the development tools
diff --git a/.azure-pipelines/jobs/test-windows.yml b/.azure-pipelines/jobs/test-windows.yml
index 1a933a6934b..a007a969eb8 100644
--- a/.azure-pipelines/jobs/test-windows.yml
+++ b/.azure-pipelines/jobs/test-windows.yml
@@ -3,15 +3,13 @@ parameters:
 
 jobs:
 - job: Test_Primary
+  dependsOn: Developer_Tooling
   displayName: Test Primary
 
   pool:
     vmImage: ${{ parameters.vmImage }}
   strategy:
     matrix:
-      Python27-x86:
-        python.version: '2.7'
-        python.architecture: x86
       Python27-x64:
         python.version: '2.7'
         python.architecture: x64
@@ -29,6 +27,14 @@ jobs:
       Python38-x64:
         python.version: '3.8'
         python.architecture: x64
+      PyPy2:
+        python.version: '2.7'
+        python.architecture: x64
+        python.flavor: pypy
+      PyPy3:
+        python.version: '3.5'
+        python.architecture: x64
+        python.flavor: pypy
     maxParallel: 6
 
   steps:
@@ -48,6 +54,9 @@ jobs:
   strategy:
     matrix:
       # This is for Windows, so test x86 builds
+      Python27-x86:
+        python.version: '2.7'
+        python.architecture: x86
       Python35-x86:
         python.version: '3.5'
         python.architecture: x86
diff --git a/.azure-pipelines/jobs/test.yml b/.azure-pipelines/jobs/test.yml
deleted file mode 100644
index cadf99a51f7..00000000000
--- a/.azure-pipelines/jobs/test.yml
+++ /dev/null
@@ -1,41 +0,0 @@
-parameters:
-  vmImage:
-
-jobs:
-- job: Test_Primary
-  displayName: Test Primary
-
-  pool:
-    vmImage: ${{ parameters.vmImage }}
-  strategy:
-    matrix:
-      Python27:
-        python.version: '2.7'
-        python.architecture: x64
-      Python36:
-        python.version: '3.6'
-        python.architecture: x64
-    maxParallel: 2
-
-  steps:
-  - template: ../steps/run-tests.yml
-
-- job: Test_Secondary
-  displayName: Test Secondary
-  # Run after Test_Primary so we don't devour time and jobs if tests are going to fail
-  dependsOn: Test_Primary
-
-  pool:
-    vmImage: ${{ parameters.vmImage }}
-  strategy:
-    matrix:
-      Python35:
-        python.version: '3.5'
-        python.architecture: x64
-      Python37:
-        python.version: '3.7'
-        python.architecture: x64
-    maxParallel: 3
-
-  steps:
-  - template: ../steps/run-tests.yml
diff --git a/.azure-pipelines/linux.yml b/.azure-pipelines/linux.yml
deleted file mode 100644
index 6965a15fc6d..00000000000
--- a/.azure-pipelines/linux.yml
+++ /dev/null
@@ -1,8 +0,0 @@
-jobs:
-- template: jobs/test.yml
-  parameters:
-    vmImage: ubuntu-16.04
-
-- template: jobs/package.yml
-  parameters:
-    vmImage: ubuntu-16.04
diff --git a/.azure-pipelines/macos.yml b/.azure-pipelines/macos.yml
deleted file mode 100644
index 85c2a0246af..00000000000
--- a/.azure-pipelines/macos.yml
+++ /dev/null
@@ -1,8 +0,0 @@
-jobs:
-- template: jobs/test.yml
-  parameters:
-    vmImage: macos-10.14
-
-- template: jobs/package.yml
-  parameters:
-    vmImage: macos-10.14
diff --git a/.azure-pipelines/steps/run-tests.yml b/.azure-pipelines/steps/run-tests.yml
deleted file mode 100644
index 64163a5be8b..00000000000
--- a/.azure-pipelines/steps/run-tests.yml
+++ /dev/null
@@ -1,25 +0,0 @@
-steps:
-- task: UsePythonVersion@0
-  displayName: Use Python $(python.version)
-  inputs:
-    versionSpec: '$(python.version)'
-
-- bash: pip install --upgrade setuptools tox
-  displayName: Install Tox
-
-- script: tox -e py -- -m unit -n auto --junit-xml=junit/unit-test.xml
-  displayName: Tox run unit tests
-
-# Run integration tests in two groups so we will fail faster if there is a failure in the first group
-- script: tox -e py -- -m integration -n auto --duration=5 -k "not test_install" --junit-xml=junit/integration-test-group0.xml
-  displayName: Tox run Group 0 integration tests
-
-- script: tox -e py -- -m integration -n auto --duration=5 -k "test_install" --junit-xml=junit/integration-test-group1.xml
-  displayName: Tox run Group 1 integration tests
-
-- task: PublishTestResults@2
-  displayName: Publish Test Results
-  inputs:
-    testResultsFiles: junit/*.xml
-    testRunTitle: 'Python $(python.version)'
-  condition: succeededOrFailed()
diff --git a/.azure-pipelines/windows.yml b/.azure-pipelines/windows.yml
index 9d1bf5385d0..ced172e5583 100644
--- a/.azure-pipelines/windows.yml
+++ b/.azure-pipelines/windows.yml
@@ -1,4 +1,9 @@
 jobs:
+
+- template: jobs/dev-tools.yml
+  parameters:
+    vmImage: vs2017-win2016
+
 - template: jobs/test-windows.yml
   parameters:
     vmImage: vs2017-win2016
diff --git a/.github/workflows/macos.yml b/.github/workflows/macos.yml
new file mode 100644
index 00000000000..4fbe34fba9e
--- /dev/null
+++ b/.github/workflows/macos.yml
@@ -0,0 +1,62 @@
+name: MacOS
+
+on:
+  push:
+  pull_request:
+  schedule:
+  # Run every Friday at 18:02 UTC
+  # https://crontab.guru/#2_18_*_*_5
+  - cron: 2 18 * * 5
+
+jobs:
+  dev-tools:
+    name: Developer Tooling
+    runs-on: macos-latest
+
+    env:
+      TOXENV: lint,docs,vendoring
+
+    steps:
+
+    # Setup Python and git.
+    - uses: actions/checkout@master
+
+    - name: Set up Python 3.8
+      uses: actions/setup-python@v1
+      with:
+        python-version: 3.8
+    - name: Pre-configure global Git settings
+      run: |
+        git config --global user.email "pypa-dev@googlegroups.com"
+        git config --global user.name "pip"
+
+    # Set up caching
+    - name: set PY
+      run: echo "::set-env name=PY::$(python -VV | sha256sum | cut -d' ' -f1)"
+
+    - name: Storing pip's cache
+      uses: actions/cache@v1
+      with:
+        path: ~/.cache/pip
+        key: ${{ runner.os }}-pip-${{ hashFiles('tools/requirements/tests.txt') }}-${{ hashFiles('tools/requirements/docs.txt') }}-${{ hashFiles('tox.ini') }}
+        restore-keys: |
+          ${{ runner.os }}-pip-
+          ${{ runner.os }}-
+
+    - name: Storing pre-commit's cache
+      uses: actions/cache@v1
+      with:
+        path: ~/.cache/pre-commit
+        key: pre-commit|2020-02-14|${{ env.PY }}|${{ hashFiles('.pre-commit-config.yaml') }}
+
+    # Update tooling
+    - name: Update setuptools
+      run: python -m pip install --upgrade setuptools
+    - name: Install tox
+      run: python -m pip install --upgrade tox
+    - name: Log the list of packages
+      run: python -m pip freeze --all
+
+    # Run checks with tox
+    - name: Run tox
+      run: python -m tox
diff --git a/.github/workflows/python-linters.yml b/.github/workflows/python-linters.yml
deleted file mode 100644
index 0b9bb0a2e44..00000000000
--- a/.github/workflows/python-linters.yml
+++ /dev/null
@@ -1,97 +0,0 @@
-name: >-
-  🤖
-  Code quality
-
-on:
-  push:
-  pull_request:
-  schedule:
-  # Run every Friday at 18:02 UTC
-  # https://crontab.guru/#2_18_*_*_5
-  - cron: 2 18 * * 5
-
-jobs:
-  linters:
-    name: >-
-      ${{ matrix.env.TOXENV }}/${{ matrix.python-version }}@${{ matrix.os }}
-    runs-on: ${{ matrix.os }}
-    strategy:
-      # max-parallel: 5
-      matrix:
-        python-version:
-        - 3.8
-        os:
-        - ubuntu-latest
-        - windows-latest
-        - macos-latest
-        env:
-        - TOXENV: docs
-        - TOXENV: lint
-        - TOXENV: vendoring
-
-    env:
-      TOX_PARALLEL_NO_SPINNER: 1
-
-    steps:
-    - uses: actions/checkout@master
-    - name: Set up Python ${{ matrix.python-version }}
-      uses: actions/setup-python@v1
-      with:
-        python-version: ${{ matrix.python-version }}
-    - name: Log Python version
-      run: >-
-        python --version
-    - name: Log Python location
-      run: >-
-        which python
-    - name: Log Python env
-      run: >-
-        python -m sysconfig
-    - name: Pip cache
-      uses: actions/cache@v1
-      with:
-        path: ~/.cache/pip
-        key: ${{ runner.os }}-pip-${{ hashFiles('tools/requirements/tests.txt') }}-${{ hashFiles('tools/requirements/docs.txt') }}-${{ hashFiles('tox.ini') }}
-        restore-keys: |
-          ${{ runner.os }}-pip-
-          ${{ runner.os }}-
-    - name: set PY
-      run: echo "::set-env name=PY::$(python -VV | sha256sum | cut -d' ' -f1)"
-    - uses: actions/cache@v1
-      with:
-        path: ~/.cache/pre-commit
-        key: pre-commit|2020-02-14|${{ env.PY }}|${{ hashFiles('.pre-commit-config.yaml') }}
-    - name: Pre-configure global Git settings
-      run: |
-        git config --global user.email "pypa-dev@googlegroups.com"
-        git config --global user.name "pip"
-    - name: Update setuptools
-      run: >-
-        python -m pip install --upgrade setuptools
-    - name: Install tox
-      run: >-
-        python -m pip install --upgrade tox tox-venv
-    - name: Log the list of packages
-      run: >-
-        python -m pip freeze --all
-    - name: 'Initialize tox envs: ${{ matrix.env.TOXENV }}'
-      run: >-
-        python -m
-        tox
-        --parallel auto
-        --notest
-        --skip-missing-interpreters false
-      env: ${{ matrix.env }}
-    - name: Pre-fetch pre-commit hooks
-      # This is to separate test step from deps install
-      if: matrix.env.TOXENV == 'lint'
-      run: >-
-        .tox/lint/${{ runner.os == 'Windows' && 'Scripts' || 'bin' }}/python -m
-        pre_commit
-        install-hooks
-    - name: Test with tox
-      run: >-
-        python -m
-        tox
-        --parallel auto
-      env: ${{ matrix.env }}
diff --git a/.travis.yml b/.travis.yml
index 7259b473a45..e81bb482979 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -13,11 +13,9 @@ stages:
 
 jobs:
   include:
-    # Basic Checks
+    # Developer Tooling
     - stage: primary
-      env: TOXENV=docs
-    - env: TOXENV=lint
-    - env: TOXENV=vendoring
+      env: TOXENV=lint,docs,vendoring
     # Latest CPython
     - env: GROUP=1
       python: 2.7
diff --git a/docs/html/development/ci.rst b/docs/html/development/ci.rst
index dbd80eb6cef..d0ea74a8ae9 100644
--- a/docs/html/development/ci.rst
+++ b/docs/html/development/ci.rst
@@ -34,28 +34,30 @@ and on different architectures:
   - x64
   - x86
 
-so 42 hypothetical interpreters.
+so 42 hypothetical combinations.
 
 
 Checks
 ======
 
-``pip`` CI runs different kind of tests:
+``pip`` CI runs various "checks":
 
-- lint (defined in ``.pre-commit-config.yaml``)
-- docs
-- vendoring (is the ``src/_internal/_vendor`` directory cleanly vendored)
-- unit tests (present in ``tests/unit``)
-- "integration" tests (mostly present in ``tests/functional``)
-- package (test the packaging steps)
+- Development tooling
+  - docs (does the documentation build correctly?)
+  - lint (automated code quality checks, run with ``pre-commit``)
+  - vendoring (is ``src/pip/_vendor`` correctly constructed?)
+- Tests
+  - unit tests (present in ``tests/unit``)
+  - "integration" tests (mostly present in ``tests/functional``)
+- Packaging (test the packaging steps)
 
-Since lint, docs, vendoring and package tests only need to run on a pip
-developer/contributor machine, they only need to be tested on the x64 variant
-of the 3 different operating systems, and when an interpreter needs to be
-specified it's ok to require the latest CPython interpreter.
+We run development tooling checks on the latest CPython (x64), on every
+OS. This helps ensure they'll also run on a pip developer/contributor's
+machine regardless of the OS they use.
 
-So only unit tests and integration tests would need to be run with the different
-interpreters.
+We try to run the tests on as many interpreter-OS-architecture
+combinations as we can, without having a significant slowdown on our
+productivity due to CI wait times.
 
 
 Services
@@ -65,13 +67,20 @@ pip test suite and checks are distributed on three different platforms that
 provides free executors for open source packages:
 
   - `Travis CI`_ (Used for Linux)
-  - `Azure DevOps CI`_ (Linux, MacOS & Windows tests)
-  - `GitHub Actions`_ (Linux, MacOS & Windows tests)
+  - `Azure DevOps CI`_ (Used for Windows)
+  - `GitHub Actions`_ (Used for MacOS)
 
 .. _`Travis CI`: https://travis-ci.org/
 .. _`Azure DevOps CI`: https://azure.microsoft.com/en-us/services/devops/
 .. _`GitHub Actions`: https://github.com/features/actions
 
+TODO
+
+- how many workers we get per-CI-service.
+- add links to "most relevant resources" for each CI-service.
+- describe how our runs are set up for short-circuiting on failures in
+  linting / documentation / vendoring / unit tests / integration tests.
+
 
 Current run tests
 =================
@@ -82,18 +91,18 @@ Developer tasks
 ======== =============== ================ ================== ============
    OS          docs            lint           vendoring        packages
 ======== =============== ================ ================== ============
-Linux     Travis, Github  Travis, Github    Travis, Github      Azure
-Windows                                                         Azure
-MacOS                                                           Azure
+Linux     Travis          Travis            Travis
+Windows   Azure           Azure             Azure               Azure
+MacOS     GitHub          GitHub            GitHub
 ======== =============== ================ ================== ============
 
 Actual testing
 --------------
 
 +------------------------------+---------------+-----------------+
-|       **interpreter**        |   **unit**    | **integration** |
+|       **combination**        |   **unit**    | **integration** |
 +-----------+----------+-------+---------------+-----------------+
-|           |          | CP2.7 |   Azure       |   Azure         |
+|           |          | CP2.7 |   Azure       |                 |
 |           |          +-------+---------------+-----------------+
 |           |          | CP3.5 |   Azure       |                 |
 |           |          +-------+---------------+-----------------+
@@ -117,9 +126,9 @@ Actual testing
 |           |          +-------+---------------+-----------------+
 |           |          | CP3.8 |   Azure       |   Azure         |
 |           |          +-------+---------------+-----------------+
-|           |          | PyPy  |               |                 |
+|           |          | PyPy  |   Azure       |   Azure         |
 |           |          +-------+---------------+-----------------+
-|           |          | PyPy3 |               |                 |
+|           |          | PyPy3 |   Azure       |   Azure         |
 +-----------+----------+-------+---------------+-----------------+
 |           |          | CP2.7 |               |                 |
 |           |          +-------+---------------+-----------------+
@@ -135,13 +144,13 @@ Actual testing
 |           |          +-------+---------------+-----------------+
 |           |          | PyPy3 |               |                 |
 |   Linux   +----------+-------+---------------+-----------------+
-|           |          | CP2.7 | Travis,Azure  |  Travis,Azure   |
+|           |          | CP2.7 |   Travis      |   Travis        |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.5 | Travis,Azure  |  Travis,Azure   |
+|           |          | CP3.5 |   Travis      |   Travis        |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.6 | Travis,Azure  |  Travis,Azure   |
+|           |          | CP3.6 |   Travis      |   Travis        |
 |           |          +-------+---------------+-----------------+
-|           |   x64    | CP3.7 | Travis,Azure  |  Travis,Azure   |
+|           |   x64    | CP3.7 |   Travis      |   Travis        |
 |           |          +-------+---------------+-----------------+
 |           |          | CP3.8 |   Travis      |   Travis        |
 |           |          +-------+---------------+-----------------+
@@ -163,13 +172,13 @@ Actual testing
 |           |          +-------+---------------+-----------------+
 |           |          | PyPy3 |               |                 |
 |   MacOS   +----------+-------+---------------+-----------------+
-|           |          | CP2.7 |   Azure       |   Azure         |
+|           |          | CP2.7 |               |                 |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.5 |   Azure       |   Azure         |
+|           |          | CP3.5 |               |                 |
 |           |          +-------+---------------+-----------------+
-|           |          | CP3.6 |   Azure       |   Azure         |
+|           |          | CP3.6 |               |                 |
 |           |          +-------+---------------+-----------------+
-|           |   x64    | CP3.7 |   Azure       |   Azure         |
+|           |   x64    | CP3.7 |               |                 |
 |           |          +-------+---------------+-----------------+
 |           |          | CP3.8 |               |                 |
 |           |          +-------+---------------+-----------------+