diff --git a/.github/workflows/send-pull-request.yml b/.github/workflows/send-pull-request.yml
index 0ebe174..57577ca 100644
--- a/.github/workflows/send-pull-request.yml
+++ b/.github/workflows/send-pull-request.yml
@@ -1,20 +1,57 @@
-name: 'Create a PR based on validation'
-
-on: 
-    workflow_dispatch: {} 
+name: "Repository Hygiene Check"
+on:
+  push:
+    branches:
+      - 'main'
+  workflow_dispatch:
 
 jobs:
-  repolinter-action:
+  check-first-run:
+    name: Check For First Run
+    runs-on: ubuntu-latest
+    outputs:
+      should_run: ${{ steps.check.outputs.should_run }}
+    permissions:
+      contents: read
+      pull-requests: write
+    steps:
+      - uses: actions/checkout@v4
+      - id: check
+        run: |
+          # If manually triggered, always run
+
+          if [[ "${{ github.event_name }}" == "workflow_dispatch" ]]; then
+            echo "should_run=true" >> $GITHUB_OUTPUT
+            exit 0
+
+          fi
+          
+          # Check if initialization label exists
+
+          has_label=$(gh label list --json name | jq '.[] | select(.name=="repolinter-initialized")')
+
+          if [[ -z "$has_label" ]]; then
+            # First time - create label and allow run
+            gh label create repolinter-initialized --description "Marks repo as having run initial repolinter check"
+            echo "should_run=true" >> $GITHUB_OUTPUT
+          else
+            echo "should_run=false" >> $GITHUB_OUTPUT
+
+          fi
+        env:
+          GITHUB_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+
+  repolinter-checks:
+    name: Tier 2 Checks
+    needs: check-first-run
+    if: needs.check-first-run.outputs.should_run == 'true'
     runs-on: ubuntu-latest
-    name: Run Repolinter
     permissions:
       contents: write
       pull-requests: write
     steps:
-      - name: Checkout Repo
-        uses: actions/checkout@v4
-      - name: 'Run Repolinter'
-        uses: DSACMS/repolinter-action@main
+      - uses: DSACMS/repolinter-action@main
         with:
           output_type: 'pull-request'
-          pull_request_labels: 'repolinter, cms-oss, cms-gov'
\ No newline at end of file
+          pull_request_labels: 'repolinter-initialized, cms-oss, cms-gov'
+          token: ${{ secrets.REPOLINTER_AUTO_TOKEN }}
\ No newline at end of file