diff --git a/.github/workflows/release-insiders.yml b/.github/workflows/release-insiders.yml
index e9661feb3..b61d27948 100644
--- a/.github/workflows/release-insiders.yml
+++ b/.github/workflows/release-insiders.yml
@@ -56,3 +56,18 @@ jobs:
         env:
           CI: true
           NODE_AUTH_TOKEN: ${{ secrets.NPM_TOKEN }}
+
+      - name: Trigger Tailwind Play update
+        uses: actions/github-script@v6
+        with:
+          github-token: ${{ secrets.TAILWIND_PLAY_TOKEN }}
+          script: |
+            await github.rest.actions.createWorkflowDispatch({
+              owner: 'tailwindlabs',
+              repo: 'play.tailwindcss.com',
+              ref: 'master',
+              workflow_id: 'upgrade-tailwindcss.yml',
+              inputs: {
+                insidersVersion: '0.0.0-insiders.${{ steps.vars.outputs.sha_short }}'
+              }
+            })