diff --git a/.github/labeler.yml b/.github/labeler.yml
index 7cc6631b04..4b11970fbc 100644
--- a/.github/labeler.yml
+++ b/.github/labeler.yml
@@ -2,42 +2,49 @@
 
 # Add 'repo' label to any root file changes
 "Area: Repo":
-  - "*"
+  - changed-files:
+      - any-glob-to-any-file: "*/**"
 
 "Area: Primitives":
-  - packages/paste-core/primitives/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-core/primitives/**/*
 
 "Area: Layout":
-  - packages/paste-core/layout/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-core/layout/**/*
 
 "Area: Components":
-  - packages/paste-core/components/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-core/components/**/*
 
 "Area: Core bundle":
-  - packages/paste-core/core-bundle/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-core/core-bundle/**/*
 
 "Area: Doc Site":
-  - packages/paste-website/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-website/**/*
 
 "Area: Theme":
-  - packages/paste-theme/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-theme/**/*
 
 "Area: Tokens":
-  - packages/paste-design-tokens/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-design-tokens/**/*
 
 "Area: Storybook":
-  - .storybook/**/*
+  - changed-files:
+      - any-glob-to-any-file: .storybook/**/*
 
 "Area: Infrastructure":
-  - .eslint/**/*
-  - .github/**/*
-  - .jest/**/*
-  - .vscode/**/*
-  - tools/**/*
+  - changed-files:
+      - any-glob-to-any-file: [".github/**/*", ".jest/**/*", ".storybook/**/*", ".vscode/**/*", "tools/**/*"]
 
 "Type: Documentation":
-  - packages/paste-website/src/pages/**/*
+  - changed-files:
+      - any-glob-to-any-file: packages/paste-website/src/pages/**/*
 
 "Type: Tests":
-  - "**/__tests__/**/*"
-  - cypress/**/*
+  - changed-files:
+      - any-glob-to-any-file: ["**/__tests__/**/*", "cypress/**/*"]
diff --git a/.github/opened-pr-contribution-labeler.yml b/.github/opened-pr-contribution-labeler.yml
new file mode 100644
index 0000000000..46b1e143d0
--- /dev/null
+++ b/.github/opened-pr-contribution-labeler.yml
@@ -0,0 +1,6 @@
+# https://github.com/actions/labeler
+
+# Add 'Contribution' label to any opened PR when author external to team
+"Contribution":
+  - changed-files:
+      - any-glob-to-any-file: "*/**"
diff --git a/.github/opened-pr-labeler.yml b/.github/opened-pr-labeler.yml
deleted file mode 100644
index 3b77ee3001..0000000000
--- a/.github/opened-pr-labeler.yml
+++ /dev/null
@@ -1,5 +0,0 @@
-# https://github.com/actions/labeler
-
-# Add 'Status: Do Not Merge' label to any newly opened PR
-"Status: Do Not Merge":
-  - "**/*"
diff --git a/.github/workflows/on_pull_request.yml b/.github/workflows/on_pull_request.yml
index 457fc1fc34..7dc9548a95 100644
--- a/.github/workflows/on_pull_request.yml
+++ b/.github/workflows/on_pull_request.yml
@@ -382,7 +382,8 @@ jobs:
 
   storybook_tests:
     name: Storybook test runner
-    runs-on: ubuntu-latest
+    # Causes playwrite issues in latest versions. Upgrading deps causes violations in the storybook tests.
+    runs-on: ubuntu-22.04
     timeout-minutes: 20
     needs: chromatic
     strategy:
@@ -450,7 +451,7 @@ jobs:
       - name: Checkout Repo
         uses: actions/checkout@v4
 
-      - uses: actions/labeler@v4
+      - uses: actions/labeler@v5
         with:
           repo-token: "${{ secrets.GITHUB_TOKEN }}"
           sync-labels: true
diff --git a/.github/workflows/on_pull_request_open.yml b/.github/workflows/on_pull_request_open.yml
index b76c95762e..6c7c415904 100644
--- a/.github/workflows/on_pull_request_open.yml
+++ b/.github/workflows/on_pull_request_open.yml
@@ -5,13 +5,30 @@ on:
     types: [opened]
 
 jobs:
-  pr-triage:
+  pr-context-labeler:
     runs-on: ubuntu-latest
     steps:
-      - name: Auto labeller
-        uses: actions/labeler@v4
+      - name: Checkout Repo
+        uses: actions/checkout@v4
+
+      - name: Check user for team affiliation
+        uses: tspascoal/get-user-teams-membership@v2
+        id: teamAffiliation
+        with:
+          GITHUB_TOKEN: "${{ secrets.PAT_GH_READ_ORG }}"
+          username: "${{ github.actor }}"
+          # List of all teams for dsys
+          team: "[Design Systems PD,design-systems,Design Systems Eng,Design Systems Eng Leads]"
+
+      - name: Debug in group
+        run: echo "${{ github.actor }} is team member ${{ steps.teamAffiliation.outputs.isTeamMember }}"
+
+      - name: Auto contribution labeler
+        if: ${{ steps.teamAffiliation.outputs.isTeamMember == 'false' }}
+        uses: actions/labeler@v5
         with:
           repo-token: "${{ secrets.GITHUB_TOKEN }}"
-          configuration-path: .github/opened-pr-labeler.yml
+          configuration-path: .github/opened-pr-contribution-labeler.yml
+
       - name: Assign Author
         uses: technote-space/assign-author@v1