diff --git a/.github/workflows/fleet-and-orbit.yml b/.github/workflows/fleet-and-orbit.yml
index 51f182efcd..46c36ec7c2 100644
--- a/.github/workflows/fleet-and-orbit.yml
+++ b/.github/workflows/fleet-and-orbit.yml
@@ -196,14 +196,19 @@ jobs:
 
     # Docker needs to be installed manually on macOS.
     # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
+    # FIXME: lock Docker version to 4.10.0 as newer versions fail to initialize
     - name: Install Docker
+      timeout-minutes: 10
+      if: matrix.os == 'macos-latest'
       run: |
-        # fixme: lock Docker version to 4.10.0 as newer versions fail to initialize
-        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb && brew install docker.rb
+        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb
+        brew install --cask docker.rb
         sudo /Applications/Docker.app/Contents/MacOS/Docker --unattended --install-privileged-components
         open -a /Applications/Docker.app --args --unattended --accept-license
         echo "Waiting for Docker to start up..."
-        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do sleep 1; done
+        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do
+          sleep 1;
+        done
         echo "Docker is ready."
 
     - name: Build Repository and run TUF server
diff --git a/.github/workflows/fleetctl-preview-latest.yml b/.github/workflows/fleetctl-preview-latest.yml
index 88abc331a0..70ff353a72 100644
--- a/.github/workflows/fleetctl-preview-latest.yml
+++ b/.github/workflows/fleetctl-preview-latest.yml
@@ -33,17 +33,21 @@ jobs:
     runs-on: ${{ matrix.os }}
     steps:
 
+    # Docker needs to be installed manually on macOS.
+    # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
+    # FIXME: lock Docker version to 4.10.0 as newer versions fail to initialize
     - name: Install Docker
-      # Docker needs to be installed manually on macOS.
-      if: contains(matrix.os, 'macos')
-      # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
+      timeout-minutes: 10
+      if: matrix.os == 'macos-latest'
       run: |
-        # fixme: lock Docker version to 4.10.0 as newer versions fail to initialize
-        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb && brew install docker.rb
+        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb
+        brew install --cask docker.rb
         sudo /Applications/Docker.app/Contents/MacOS/Docker --unattended --install-privileged-components
         open -a /Applications/Docker.app --args --unattended --accept-license
         echo "Waiting for Docker to start up..."
-        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do sleep 1; done
+        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do
+          sleep 1;
+        done
         echo "Docker is ready."
 
     - name: Install Go
@@ -81,4 +85,4 @@ jobs:
         path: |
           fleet-logs.txt
           orbit.log
-          osquery_result_status_logs
\ No newline at end of file
+          osquery_result_status_logs
diff --git a/.github/workflows/fleetctl-preview.yml b/.github/workflows/fleetctl-preview.yml
index b64e1fe200..f4e2f42eb2 100644
--- a/.github/workflows/fleetctl-preview.yml
+++ b/.github/workflows/fleetctl-preview.yml
@@ -19,17 +19,22 @@ jobs:
         os: [ubuntu-20.04, ubuntu-18.04, macos-11, macos-12]
     runs-on: ${{ matrix.os }}
     steps:
+
+    # Docker needs to be installed manually on macOS.
+    # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
+    # FIXME: lock Docker version to 4.10.0 as newer versions fail to initialize
     - name: Install Docker
-      # Docker needs to be installed manually on macOS.
+      timeout-minutes: 10
       if: contains(matrix.os, 'macos')
-      # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
       run: |
-        # fixme: lock Docker version to 4.10.0 as newer versions fail to initialize
-        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb && brew install docker.rb
+        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb
+        brew install --cask docker.rb
         sudo /Applications/Docker.app/Contents/MacOS/Docker --unattended --install-privileged-components
         open -a /Applications/Docker.app --args --unattended --accept-license
         echo "Waiting for Docker to start up..."
-        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do sleep 1; done
+        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do
+          sleep 1;
+        done
         echo "Docker is ready."
 
     - name: Start tunnel
@@ -85,4 +90,4 @@ jobs:
         path: |
           fleet-logs.txt
           orbit.log
-          osquery_result_status_logs
\ No newline at end of file
+          osquery_result_status_logs
diff --git a/.github/workflows/test-packaging.yml b/.github/workflows/test-packaging.yml
index c3141478dc..84103a18a6 100644
--- a/.github/workflows/test-packaging.yml
+++ b/.github/workflows/test-packaging.yml
@@ -29,17 +29,22 @@ jobs:
     runs-on: ${{ matrix.os }}
 
     steps:
+
+    # Docker needs to be installed manually on macOS.
+    # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
+    # FIXME: lock Docker version to 4.10.0 as newer versions fail to initialize
     - name: Install Docker
-      timeout-minutes: 60
+      timeout-minutes: 10
       if: matrix.os == 'macos-latest'
-      # From https://github.com/docker/for-mac/issues/2359#issuecomment-943131345
       run: |
-        # fixme: lock Docker version to 4.10.0 as newer versions fail to initialize
-        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb && brew install docker.rb
+        curl -L https://raw.githubusercontent.com/Homebrew/homebrew-cask/c65030146a5cf2070c2499b6c68e2c3495c99731/Casks/docker.rb > docker.rb
+        brew install --cask docker.rb
         sudo /Applications/Docker.app/Contents/MacOS/Docker --unattended --install-privileged-components
         open -a /Applications/Docker.app --args --unattended --accept-license
         echo "Waiting for Docker to start up..."
-        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do sleep 1; done
+        while ! /Applications/Docker.app/Contents/Resources/bin/docker info &>/dev/null; do
+          sleep 1;
+        done
         echo "Docker is ready."
 
     - name: Pull fleetdm/wix