diff --git a/.github/labeler.yml b/.github/labeler.yml
new file mode 100644
index 00000000..79f403a9
--- /dev/null
+++ b/.github/labeler.yml
@@ -0,0 +1,10 @@
+# Configuration for automatic PR labeling based on file changes
+# https://github.com/actions/labeler
+
+# CLI - Command Line Interface
+"area: cli":
+  - changed-files:
+    - any-glob-to-any-file: 
+      - 'Sources/CLI/**/*'
+      - 'Sources/ContainerCommands/**/*'
+
diff --git a/.github/workflows/labeler.yml b/.github/workflows/labeler.yml
new file mode 100644
index 00000000..196df1ec
--- /dev/null
+++ b/.github/workflows/labeler.yml
@@ -0,0 +1,32 @@
+name: "Pull Request Labeler"
+
+on:
+  pull_request:
+    types: [opened]
+
+permissions:
+  contents: read
+  pull-requests: write
+
+jobs:
+  label:
+    name: Label Pull Request
+    if: github.repository == 'apple/container'
+    runs-on: ubuntu-latest
+    outputs:
+      labels-applied: ${{ steps.labeler.outputs.labels-applied }}
+    steps:
+      - name: Checkout repository
+        uses: actions/checkout@v4
+        with:
+          token: ${{ secrets.GITHUB_TOKEN }}
+
+      - name: Apply labels based on file changes
+        id: labeler
+        uses: actions/labeler@v5
+        with:
+          repo-token: ${{ secrets.GITHUB_TOKEN }}
+          configuration-path: .github/labeler.yml
+          sync-labels: true
+
+