diff --git a/.github/workflows/poll.yml b/.github/workflows/poll.yml
new file mode 100644
index 0000000..963b6e6
--- /dev/null
+++ b/.github/workflows/poll.yml
@@ -0,0 +1,51 @@
+---
+name: Release
+
+on: # yamllint disable-line rule:truthy
+  schedule:
+    # wednesday, friday at 00:00
+    - cron: '0 0 * * 3,5'
+  workflow_dispatch:
+
+jobs:
+  release:
+    name: Poll OpenSSL Website
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v3
+      - env:
+          GITHUB_TOKEN: ${{ secrets.token }}
+          DEBUG: ${{ runner.debug == '1' && '1' || '' }}
+        run: |
+          if [ -n "${DEBUG:-}" ]; then
+            set -x
+          fi
+
+          fresh="$(
+            grep -Eo -m1 -i '1\.1\.1.*available' <(
+              curl -Ls 'https://www.openssl.org/news/newslog.html'
+            ) | cut -d' ' -f1
+          )"
+
+          stale="$(cat .env)"
+
+          message="chore(*): update OpenSSL to ${fresh}"
+
+          if [[ "$fresh" != "$stale" ]] ; then
+
+            # PR already created for fresh version
+            if gh pr list | grep "$message"; then
+              exit 0
+            fi
+
+            git checkout -b chore/openssl-${fresh}
+
+            echo "$fresh" > .env
+            git add .env
+            git commit -m "chore(*): update OpenSSL to ${fresh}"
+
+            pr="$(gh pr create --fill | grep -Eo '\d+$')"
+
+            gh pr merge --auto "$pr"
+          fi