diff --git a/.github/workflows/test.yml b/.github/workflows/test.yml
index 0eddf360..7fd10378 100644
--- a/.github/workflows/test.yml
+++ b/.github/workflows/test.yml
@@ -42,7 +42,7 @@ jobs:
     - name: Install Visual C++ for Python 2.7
       if: runner.os == 'Windows'
       run: |
-        choco install vcpython27 -f -y
+        choco upgrade vcpython27 -y
 
     - name: Get PR labels
       id: pr-labels
diff --git a/.travis.yml b/.travis.yml
index 1a866ea1..bd89e869 100644
--- a/.travis.yml
+++ b/.travis.yml
@@ -36,9 +36,9 @@ jobs:
       os: windows
       language: shell
       before_install:
-       - choco install python3 --version 3.6.8 --no-progress -y
-       # Update root certificates to fix SSL error; see http://www.chawn.com/RootCerts.htm
-       - powershell "md C:\temp\certs; CertUtil -generateSSTFromWU C:\temp\certs\RootStore.sst; Get-ChildItem -Path C:\\temp\certs\Rootstore.sst | Import-Certificate -CertStoreLocation Cert:\\LocalMachine\\Root\\ | out-null"
+        - choco upgrade python3 -y --version 3.6.8 --limit-output
+        # Update root certificates to fix SSL error; see http://www.chawn.com/RootCerts.htm
+        - powershell "md C:\temp\certs; CertUtil -generateSSTFromWU C:\temp\certs\RootStore.sst; Get-ChildItem -Path C:\\temp\certs\Rootstore.sst | Import-Certificate -CertStoreLocation Cert:\\LocalMachine\\Root\\ | out-null"
       env:
         - PYTHON=C:\\Python36\\python
 
diff --git a/azure-pipelines.yml b/azure-pipelines.yml
index b144c2db..27072bb5 100644
--- a/azure-pipelines.yml
+++ b/azure-pipelines.yml
@@ -26,7 +26,7 @@ jobs:
     - task: UsePythonVersion@0
       inputs:
         versionSpec: '3.6'
-    - script: choco install vcpython27 -f -y
+    - script: choco upgrade vcpython27 -y
       displayName: Install Visual C++ for Python 2.7
     - bash: |
         python -m pip install -e ".[dev]" pytest-azurepipelines
@@ -39,7 +39,7 @@ jobs:
     - task: UsePythonVersion@0
       inputs:
         versionSpec: '3.8'
-    - script: choco install vcpython27 -f -y
+    - script: choco upgrade vcpython27 -y
       displayName: Install Visual C++ for Python 2.7
     - bash: |
         python -m pip install -e ".[dev]" pytest-azurepipelines
diff --git a/docs/setup.md b/docs/setup.md
index 2ac9512f..d4467a9d 100644
--- a/docs/setup.md
+++ b/docs/setup.md
@@ -47,7 +47,7 @@ To build Linux, Mac, and Windows wheels using GitHub Actions, create a `.github/
 
           - name: Install Visual C++ for Python 2.7
             if: runner.os == 'Windows'
-            run: choco install vcpython27 -f -y
+            run: choco upgrade vcpython27 -y
 
           - name: Build wheels
             run: pipx run cibuildwheel==1.10.0
@@ -89,7 +89,7 @@ To build Linux, Mac, and Windows wheels using GitHub Actions, create a `.github/
 
           - name: Install Visual C++ for Python 2.7
             if: runner.os == 'Windows'
-            run: choco install vcpython27 -f -y
+            run: choco upgrade vcpython27 -y
 
           - name: Build wheels
             run: python -m cibuildwheel --output-dir wheelhouse
diff --git a/examples/azure-pipelines-minimal.yml b/examples/azure-pipelines-minimal.yml
index 742af4b4..2eb148ac 100644
--- a/examples/azure-pipelines-minimal.yml
+++ b/examples/azure-pipelines-minimal.yml
@@ -31,7 +31,7 @@ jobs:
   pool: {vmImage: 'vs2017-win2016'}
   steps:
     - task: UsePythonVersion@0
-    - script: choco install vcpython27 -f -y
+    - script: choco upgrade vcpython27 -y
       displayName: Install Visual C++ for Python 2.7
     - bash: |
         set -o errexit
diff --git a/examples/github-deploy.yml b/examples/github-deploy.yml
index 249ce138..e95e7af3 100644
--- a/examples/github-deploy.yml
+++ b/examples/github-deploy.yml
@@ -28,7 +28,7 @@ jobs:
 
       - name: Install Visual C++ for Python 2.7
         if: runner.os == 'Windows'
-        run: choco install vcpython27 -f -y
+        run: choco upgrade vcpython27 -y
 
       - name: Build wheels
         uses: joerick/cibuildwheel@v1.10.0
diff --git a/examples/github-minimal.yml b/examples/github-minimal.yml
index 0ac6b853..b23bb596 100644
--- a/examples/github-minimal.yml
+++ b/examples/github-minimal.yml
@@ -15,7 +15,7 @@ jobs:
 
       - name: Install Visual C++ for Python 2.7
         if: runner.os == 'Windows'
-        run: choco install vcpython27 -f -y
+        run: choco upgrade vcpython27 -y
 
       - name: Build wheels
         uses: joerick/cibuildwheel@v1.10.0
diff --git a/examples/github-with-qemu.yml b/examples/github-with-qemu.yml
index a49b8120..9f30454e 100644
--- a/examples/github-with-qemu.yml
+++ b/examples/github-with-qemu.yml
@@ -20,7 +20,7 @@ jobs:
 
       - name: Install Visual C++ for Python 2.7
         if: runner.os == 'Windows'
-        run: choco install vcpython27 -f -y
+        run: choco upgrade vcpython27 -y
 
       - name: Set up QEMU
         if: runner.os == 'Linux'
diff --git a/examples/travis-ci-deploy.yml b/examples/travis-ci-deploy.yml
index 1658575e..a1598768 100644
--- a/examples/travis-ci-deploy.yml
+++ b/examples/travis-ci-deploy.yml
@@ -14,7 +14,7 @@ jobs:
     - os: windows
       language: shell
       before_install:
-        - choco install python --version 3.8.6
+        - choco upgrade python -y --version 3.8.6
         - export PATH="/c/Python38:/c/Python38/Scripts:$PATH"
         # make sure it's on PATH as 'python3'
         - ln -s /c/Python38/python.exe /c/Python38/python3.exe
diff --git a/examples/travis-ci-minimal.yml b/examples/travis-ci-minimal.yml
index a3a2a330..7fbc1889 100644
--- a/examples/travis-ci-minimal.yml
+++ b/examples/travis-ci-minimal.yml
@@ -20,7 +20,7 @@ jobs:
     - os: windows
       language: shell
       before_install:
-        - choco install python --version 3.8.6
+        - choco upgrade python -y --version 3.8.6
         - export PATH="/c/Python38:/c/Python38/Scripts:$PATH"
         # make sure it's on PATH as 'python3'
         - ln -s /c/Python38/python.exe /c/Python38/python3.exe
diff --git a/examples/travis-ci-test-and-deploy.yml b/examples/travis-ci-test-and-deploy.yml
index 7c8e22db..ec4deeca 100644
--- a/examples/travis-ci-test-and-deploy.yml
+++ b/examples/travis-ci-test-and-deploy.yml
@@ -14,7 +14,7 @@ python:
 before_install:
   - |
     if [[ "$TRAVIS_OS_NAME" = windows ]]; then
-        choco install python --version 3.8.6
+        choco upgrade python -y --version 3.8.6
         export PATH="/c/Python38:/c/Python38/Scripts:$PATH"
         # make sure it's on PATH as 'python3'
         ln -s /c/Python38/python.exe /c/Python38/python3.exe