diff --git a/.github/workflows/days-since-last-pin.yml b/.github/workflows/days-since-last-pin.yml
new file mode 100644
index 0000000000000..f12bcd8f5d411
--- /dev/null
+++ b/.github/workflows/days-since-last-pin.yml
@@ -0,0 +1,41 @@
+name: Days Since Last Pin
+
+on:
+  schedule:
+    - cron: "42 9 * * *"
+  workflow_dispatch:
+
+jobs:
+  compute-days-since-last-pin:
+    runs-on: ubuntu-22.04
+    permissions:
+      contents: read
+      id-token: write
+    steps:
+      - uses: actions/checkout@de0fac2e4500dabe0009e67214ff5f5447ce83dd # v6.0.2
+
+      - uses: DataDog/dd-octo-sts-action@acaa02eee7e3bb0839e4272dacb37b8f3b58ba80 # v1.0.3
+        id: octo-sts
+        with:
+          scope: DataDog/datadog-agent
+          policy: integrations-core.github.read-release-json.schedule
+
+      - name: Compute days since last pin
+        id: compute
+        env:
+          GITHUB_TOKEN: ${{ steps.octo-sts.outputs.token }}
+        run: python3 .github/workflows/scripts/days_since_last_pin.py
+
+      - name: Submit metric to Datadog
+        env:
+          DD_API_KEY: ${{ secrets.DD_API_KEY }}
+          DAYS: ${{ steps.compute.outputs.days }}
+        run: |
+          python3 - <<'EOF'
+          import json, os, time, urllib.request
+          days = int(os.environ["DAYS"])
+          payload = json.dumps({"series": [{"metric": "integrations_core.days_since_last_pin", "type": 3, "points": [{"timestamp": int(time.time()), "value": days}], "tags": ["team:agent-integrations"]}]}).encode()
+          req = urllib.request.Request("https://api.datadoghq.com/api/v2/series", data=payload, headers={"DD-API-KEY": os.environ["DD_API_KEY"], "Content-Type": "application/json"}, method="POST")
+          with urllib.request.urlopen(req) as resp:
+              print(f"Datadog API response: {json.loads(resp.read().decode())}")
+          EOF
diff --git a/.github/workflows/scripts/days_since_last_pin.py b/.github/workflows/scripts/days_since_last_pin.py
new file mode 100644
index 0000000000000..61b189e301117
--- /dev/null
+++ b/.github/workflows/scripts/days_since_last_pin.py
@@ -0,0 +1,84 @@
+import json
+import os
+import urllib.request
+from datetime import datetime, timedelta, timezone
+
+AGENT_REPO = "DataDog/datadog-agent"
+RELEASE_JSON_URL = f"https://raw.githubusercontent.com/{AGENT_REPO}/main/release.json"
+COMMITS_API_URL = f"https://api.github.com/repos/{AGENT_REPO}/commits"
+GITHUB_TOKEN = os.environ["GITHUB_TOKEN"]
+
+
+def fetch_json(url, headers=None):
+    req = urllib.request.Request(url, headers=headers or {})
+    with urllib.request.urlopen(req) as resp:
+        return json.loads(resp.read().decode())
+
+
+def get_integrations_core_version(sha):
+    raw_url = f"https://raw.githubusercontent.com/{AGENT_REPO}/{sha}/release.json"
+    req = urllib.request.Request(raw_url, headers={"Authorization": f"token {GITHUB_TOKEN}"})
+    with urllib.request.urlopen(req) as resp:
+        release = json.loads(resp.read().decode())
+    return release["dependencies"]["INTEGRATIONS_CORE_VERSION"]
+
+
+# Step 1: get current pin
+req = urllib.request.Request(RELEASE_JSON_URL, headers={"Authorization": f"token {GITHUB_TOKEN}"})
+with urllib.request.urlopen(req) as resp:
+    release_data = json.loads(resp.read().decode())
+current_pin = release_data["dependencies"]["INTEGRATIONS_CORE_VERSION"]
+print(f"Current pin: {current_pin}")
+
+# Steps 2 & 3: fetch commits to release.json from the last month, walk newest→oldest.
+# release.json is updated for many reasons beyond the integrations-core pin, so we bound by
+# time window rather than a fixed page count. If the pin has been unchanged for the full month,
+# last_pin_commit will hold the oldest commit in the window (a conservative undercount, but
+# still well above the 4-day alert threshold).
+since = (datetime.now(timezone.utc) - timedelta(days=30)).strftime("%Y-%m-%dT%H:%M:%SZ")
+last_pin_commit: dict | None = None
+pin_changed = False
+page = 1
+
+while not pin_changed:
+    page_commits = fetch_json(
+        f"{COMMITS_API_URL}?path=release.json&per_page=100&since={since}&page={page}",
+        headers={"Authorization": f"token {GITHUB_TOKEN}", "Accept": "application/vnd.github+json"},
+    )
+    if not page_commits:
+        break
+    print(f"Page {page}: fetched {len(page_commits)} commits touching release.json")
+    if last_pin_commit is None:
+        last_pin_commit = page_commits[0]  # most recent commit, used as fallback
+    for commit in page_commits:
+        sha = commit["sha"]
+        try:
+            pin_at_sha = get_integrations_core_version(sha)
+        except Exception as e:
+            print(f"Error: could not fetch release.json at {sha}: {e}")
+            raise  # fail the job; don't submit a potentially wrong metric
+        if pin_at_sha == current_pin:
+            last_pin_commit = commit
+        else:
+            pin_changed = True
+            break  # last_pin_commit is the oldest commit still on the current pin
+    page += 1
+
+# Step 4: compute days
+now_utc = datetime.now(timezone.utc)
+if last_pin_commit is None:
+    # No commits to release.json in the last 30 days — pin is at least 30 days old
+    days = 30
+    print("No commits to release.json found in the last 30 days; reporting days=30")
+else:
+    committed_at_str = last_pin_commit["commit"]["committer"]["date"]
+    committed_at = datetime.fromisoformat(committed_at_str.replace("Z", "+00:00"))
+    days = (now_utc - committed_at).days
+    print(f"Last pin commit: {last_pin_commit['sha']} at {committed_at_str}")
+    print(f"Days since last pin: {days}")
+
+# Write days to GITHUB_OUTPUT for the submit step
+github_output = os.environ.get("GITHUB_OUTPUT")
+if github_output:
+    with open(github_output, "a") as f:
+        f.write(f"days={days}\n")