diff --git a/.github/workflows/enforce-toolchain-synchronization.yml b/.github/workflows/enforce-toolchain-synchronization.yml
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+# Enforce rebasing Pull Requests if Toolchain was modified on target branch
+#
+# If new commits, which modifies toolchain files was pushed to given branch, find all PRs targeting
+# this branch, which also change toolchain files. Then, enforce rebasing them by changing
+# CI/Jenkins/toolchain check to FAILURE.
+# This prevents race condition issue when new toolchain bundle has to be built after PR is merged.
+#
+# Toolchain files:
+# * scripts/requirements-fixed.txt
+# * scripts/tools-versions-darwin.yml
+# * scripts/tools-versions-win10.yml
+# * scripts/tools-versions-linux.yml
+
+name: Enforce rebasing Pull Requests if Toolchain was modified on target branch
+
+on:
+  push:
+    branches:
+      - '**'  # Triggers on pushes to any branch
+
+jobs:
+  check-prs:
+    runs-on: ubuntu-latest
+
+    steps:
+      - name: Define list of files to check
+        id: define_files
+        run: |
+          echo "TOOLCHAIN_FILES=scripts/requirements-fixed.txt,scripts/tools-versions-linux.yml,scripts/tools-versions-darwin.yml,scripts/tools-versions-win10.yml" >> $GITHUB_ENV
+
+      - name: Checkout the repository
+        uses: actions/checkout@v4
+        with:
+          fetch-depth: 0
+          persist-credentials: false
+
+      - name: Get files modified by recent commits
+        id: get_files
+        run: |
+          echo "Modified files in this commit:"
+          git diff --name-only ${{ github.event.before }} ${{ github.sha }} > modified_files.txt
+          cat modified_files.txt
+
+      - name: Check if any watched files are modified
+        id: check_files
+        run: |
+          modified_files=$(cat modified_files.txt)
+          IFS=',' read -r -a watched_files <<< "${{ env.TOOLCHAIN_FILES }}"
+          modified=false
+          for file in "${watched_files[@]}"; do
+            if echo "$modified_files" | grep -q "$file"; then
+              echo "$file was modified."
+              modified=true
+            fi
+          done
+          echo "modified=$modified" >> $GITHUB_ENV
+
+      # App token is required to update Check Status
+      - name: Get jenkins-ncs App token
+        if: env.modified == 'true'
+        uses: actions/create-github-app-token@v1
+        id: app-token
+        with:
+          app-id: ${{ vars.JENKINS_NCS_APP_ID }}
+          private-key: ${{ secrets.JENKINS_NCS_APP_PRIVATE_KEY }}
+
+      - name: Find open pull requests targeting this branch and modyfing Toolchain files
+        if: env.modified == 'true'
+        id: find_prs
+        run: |
+          PRs=$(gh pr list --base ${{ github.ref_name }} --state open --json url,headRefName,files --jq '[.[] | select(.files[]? | .path as $file | [$file] | inside([env.TOOLCHAIN_FILES]))]')
+          echo "Found PRs: $PRs"
+          echo "prs=$PRs" >> $GITHUB_ENV
+        env:
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
+
+      - name: Set CI/Jenkins/toolchain status check to failure
+        if: env.modified == 'true' && steps.find_prs.outputs.prs != '[]'
+        env:
+          GH_TOKEN: ${{ steps.app-token.outputs.token }}
+        run: |
+          for pr in $(echo "$prs" | jq -r '.[].url'); do
+            pr_url=$(echo $pr | sed 's|https://github.com/||')
+            pr_owner=$(echo $pr_url | cut -d'/' -f1)
+            pr_repo=$(echo $pr_url | cut -d'/' -f2)
+            pr_number=$(echo $pr_url | cut -d'/' -f4)
+
+            echo "Setting CI/Jenkins/toolchain status to failure for PR: $pr"
+
+            # Get the SHA of the last commit in the PR branch
+            commit_sha=$(gh pr view $pr_number --json headRefOid --jq '.headRefOid')
+
+            # Get the Check Run ID by listing the check runs for the PR's head commit
+            check_run_id=$(gh api \
+              -H "Accept: application/vnd.github.v3+json" \
+              /repos/$pr_owner/$pr_repo/commits/$commit_sha/check-runs \
+              --jq '.check_runs[] | select(.name == "CI/Jenkins/toolchain") | .id')
+
+            # If no check run exists, create a new one; otherwise, update the existing one
+            if [ -z "$check_run_id" ]; then
+              echo "Creating new check run for PR: $pr"
+              gh api \
+                -H "Accept: application/vnd.github.v3+json" \
+                --method POST /repos/$pr_owner/$pr_repo/check-runs \
+                -f name="CI/Jenkins/toolchain" \
+                -f head_sha="$commit_sha" \
+                -f status="completed" \
+                -f conclusion="failure" \
+                -f output[title]="Rebase needed - Toolchain changed on '${{ github.ref_name }}' branch" \
+                -f output[summary]="Toolchain was modified on '${{ github.ref_name }}' and this PR has to be rebased"
+            else
+              echo "Updating existing check run with ID $check_run_id"
+              gh api \
+                -H "Accept: application/vnd.github.v3+json" \
+                --method PATCH /repos/$pr_owner/$pr_repo/check-runs/$check_run_id \
+                -f conclusion="failure" \
+                -f status="completed" \
+                -f output[title]="Rebase needed - Toolchain changed on '${{ github.ref_name }}' branch" \
+                -f output[summary]="Toolchain was modified on '${{ github.ref_name }}' and this PR has to be rebased"
+            fi
+          done