diff --git a/kubernetes/manual-trigger.yaml b/kubernetes/manual-trigger.yaml
new file mode 100644
index 0000000..18744d0
--- /dev/null
+++ b/kubernetes/manual-trigger.yaml
@@ -0,0 +1,57 @@
+---
+# Argo WorkflowTemplate — submit from the Argo UI at http://192.168.87.8
+# or via:  kubectl create job --from=cronjob/upgrade-requester manual-$(date +%Y%m%d-%H%M) -n k8s-version-tracker
+apiVersion: argoproj.io/v1alpha1
+kind: WorkflowTemplate
+metadata:
+  name: upgrade-requester-manual
+  namespace: k8s-version-tracker
+  labels:
+    app: upgrade-requester
+spec:
+  entrypoint: run-upgrade
+  serviceAccountName: upgrade-requester
+  templates:
+    - name: run-upgrade
+      container:
+        image: registry.storedbox.net/k8s-version-tracker:latest
+        imagePullPolicy: Always
+        command: ["python", "request_upgrades.py"]
+        env:
+          - name: MATTERMOST_WEBHOOK_URL
+            valueFrom:
+              secretKeyRef:
+                name: version-tracker-secrets
+                key: MATTERMOST_WEBHOOK_URL
+          - name: GITEA_TOKEN
+            valueFrom:
+              secretKeyRef:
+                name: version-tracker-secrets
+                key: GITEA_TOKEN
+          - name: GITEA_REPO_URL
+            value: "https://repo.adservio.us/ai_approver/argocd-gitops.git"
+          - name: GITEA_USERNAME
+            value: "ai_approver"
+          - name: GITEA_COMMITTER_NAME
+            value: "k8s-version-tracker"
+          - name: GITEA_COMMITTER_EMAIL
+            value: "k8s-version-tracker@themosers.club"
+          - name: APPROVAL_MIDDLEWARE_URL
+            value: "http://192.168.87.14:8085"
+          - name: APPROVAL_TIMEOUT_MINUTES
+            value: "60"
+          - name: APPROVAL_POLL_INTERVAL
+            value: "30"
+        resources:
+          requests:
+            cpu: 50m
+            memory: 128Mi
+          limits:
+            cpu: 200m
+            memory: 256Mi
+        volumeMounts:
+          - name: tmp
+            mountPath: /tmp
+  volumes:
+    - name: tmp
+      emptyDir: {}
diff --git a/kubernetes/upgrade-cronjob.yaml b/kubernetes/upgrade-cronjob.yaml
new file mode 100644
index 0000000..5187505
--- /dev/null
+++ b/kubernetes/upgrade-cronjob.yaml
@@ -0,0 +1,66 @@
+---
+apiVersion: batch/v1
+kind: CronJob
+metadata:
+  name: upgrade-requester
+  namespace: k8s-version-tracker
+  labels:
+    app: upgrade-requester
+spec:
+  # Every Monday at 09:00 UTC — one day after the Sunday version report
+  schedule: "0 9 * * 1"
+  concurrencyPolicy: Forbid
+  successfulJobsHistoryLimit: 3
+  failedJobsHistoryLimit: 3
+  jobTemplate:
+    spec:
+      # 90 minutes: 60m approval window + time to clone, update, and push
+      activeDeadlineSeconds: 5400
+      template:
+        metadata:
+          labels:
+            app: upgrade-requester
+        spec:
+          serviceAccountName: upgrade-requester
+          restartPolicy: Never
+          containers:
+            - name: upgrade-requester
+              image: registry.storedbox.net/k8s-version-tracker:latest
+              imagePullPolicy: Always
+              command: ["python", "request_upgrades.py"]
+              env:
+                - name: MATTERMOST_WEBHOOK_URL
+                  valueFrom:
+                    secretKeyRef:
+                      name: version-tracker-secrets
+                      key: MATTERMOST_WEBHOOK_URL
+                - name: GITEA_TOKEN
+                  valueFrom:
+                    secretKeyRef:
+                      name: version-tracker-secrets
+                      key: GITEA_TOKEN
+                - name: GITEA_REPO_URL
+                  value: "https://repo.adservio.us/ai_approver/argocd-gitops.git"
+                - name: GITEA_USERNAME
+                value: "ai_approver"
+              - name: GITEA_COMMITTER_NAME
+                  value: "k8s-version-tracker"
+                - name: GITEA_COMMITTER_EMAIL
+                  value: "k8s-version-tracker@themosers.club"
+                - name: APPROVAL_MIDDLEWARE_URL
+                  value: "http://192.168.87.14:8085"
+                - name: APPROVAL_TIMEOUT_MINUTES
+                  value: "60"
+                - name: APPROVAL_POLL_INTERVAL
+                  value: "30"
+              resources:
+                requests:
+                  cpu: 50m
+                  memory: 128Mi
+                limits:
+                  cpu: 200m
+                  memory: 256Mi
+
+---
+# Manual trigger:
+# kubectl create job --from=cronjob/upgrade-requester upgrade-manual -n k8s-version-tracker
diff --git a/request_upgrades.py b/request_upgrades.py
new file mode 100644
index 0000000..77f8e47
--- /dev/null
+++ b/request_upgrades.py
@@ -0,0 +1,329 @@
+#!/usr/bin/env python3
+"""
+request_upgrades.py: Kubernetes image upgrade approval workflow (GitOps).
+
+Finds outdated images in the cluster, maps them to YAML files in the ArgoCD
+gitops repo, requests Mattermost approval, then on approval commits and pushes
+the tag updates. ArgoCD auto-syncs from there — no direct kubectl patching.
+"""
+
+import os
+import re
+import shutil
+import subprocess
+import tempfile
+import time
+import logging
+from datetime import datetime, timezone
+from pathlib import Path
+
+import requests
+from kubernetes import client, config
+from packaging.version import Version, InvalidVersion
+
+from check_versions import (
+    ImageInfo,
+    get_cluster_images,
+    get_latest_version,
+)
+
+logging.basicConfig(level=logging.INFO, format="%(asctime)s %(levelname)s %(message)s")
+logger = logging.getLogger(__name__)
+
+APPROVAL_MIDDLEWARE_URL = os.environ.get("APPROVAL_MIDDLEWARE_URL", "http://192.168.87.14:8085")
+MATTERMOST_WEBHOOK_URL = os.environ["MATTERMOST_WEBHOOK_URL"]
+APPROVAL_TIMEOUT_MINUTES = int(os.environ.get("APPROVAL_TIMEOUT_MINUTES", "60"))
+APPROVAL_POLL_INTERVAL = int(os.environ.get("APPROVAL_POLL_INTERVAL", "30"))
+GITEA_TOKEN = os.environ["GITEA_TOKEN"]
+GITEA_USERNAME = os.environ.get("GITEA_USERNAME", "x-token")
+GITEA_REPO_URL = os.environ.get(
+    "GITEA_REPO_URL", "https://repo.adservio.us/ai_approver/argocd-gitops.git"
+)
+GITEA_COMMITTER_NAME = os.environ.get("GITEA_COMMITTER_NAME", "k8s-version-tracker")
+GITEA_COMMITTER_EMAIL = os.environ.get(
+    "GITEA_COMMITTER_EMAIL", "k8s-version-tracker@themosers.club"
+)
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Version check
+# ─────────────────────────────────────────────────────────────────────────────
+
+def collect_outdated(all_images: dict[str, ImageInfo]) -> list[dict]:
+    results = []
+    for ref, img in all_images.items():
+        if img.is_local or img.skip_check or img.is_floating:
+            continue
+        latest = get_latest_version(img)
+        if not latest:
+            continue
+        try:
+            is_outdated = Version(latest.lstrip("v")) > Version(img.tag.lstrip("v"))
+        except InvalidVersion:
+            is_outdated = img.tag != latest
+        if is_outdated:
+            results.append({
+                "image": ref,
+                "image_short": img.display_name,
+                "current_tag": img.tag,
+                "latest_tag": latest,
+                "new_image": ref.rsplit(":", 1)[0] + ":" + latest,
+                "pods": img.pods,
+            })
+    return results
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Git operations
+# ─────────────────────────────────────────────────────────────────────────────
+
+def _git(args: list[str], cwd: str | None = None) -> subprocess.CompletedProcess:
+    result = subprocess.run(
+        ["git"] + args,
+        cwd=cwd,
+        capture_output=True,
+        text=True,
+    )
+    if result.returncode != 0:
+        raise RuntimeError(f"git {' '.join(args)} failed:\n{result.stderr}")
+    return result
+
+
+def clone_repo(dest: str) -> None:
+    # Embed token in URL for authentication (never logged)
+    parsed = GITEA_REPO_URL.split("://", 1)
+    auth_url = f"{parsed[0]}://{GITEA_USERNAME}:{GITEA_TOKEN}@{parsed[1]}"
+    _git(["clone", "--depth=1", auth_url, dest])
+    _git(["config", "user.name", GITEA_COMMITTER_NAME], cwd=dest)
+    _git(["config", "user.email", GITEA_COMMITTER_EMAIL], cwd=dest)
+    logger.info("Cloned %s to %s", GITEA_REPO_URL, dest)
+
+
+def find_yaml_files_with_image(repo_dir: str, image_ref: str) -> list[Path]:
+    """Return all YAML files under repo_dir that contain the exact image_ref string."""
+    matches = []
+    for path in Path(repo_dir).rglob("*.yaml"):
+        if image_ref in path.read_text():
+            matches.append(path)
+    return matches
+
+
+def build_upgrade_plan(repo_dir: str, outdated: list[dict]) -> list[dict]:
+    plan = []
+    for entry in outdated:
+        files = find_yaml_files_with_image(repo_dir, entry["image"])
+        if not files:
+            logger.debug("No YAML files found for %s — skipping", entry["image"])
+            continue
+        for f in files:
+            plan.append({
+                "file": str(f.relative_to(repo_dir)),
+                "abs_path": str(f),
+                "old_image": entry["image"],
+                "new_image": entry["new_image"],
+                "image_short": entry["image_short"],
+                "current_tag": entry["current_tag"],
+                "latest_tag": entry["latest_tag"],
+            })
+    return plan
+
+
+def apply_updates(plan: list[dict]) -> list[dict]:
+    """Replace old image refs in YAML files. Returns entries that were actually changed."""
+    changed = []
+    for item in plan:
+        path = Path(item["abs_path"])
+        original = path.read_text()
+        updated = original.replace(item["old_image"], item["new_image"])
+        if updated != original:
+            path.write_text(updated)
+            changed.append(item)
+            logger.info("Updated %s: %s -> %s", item["file"], item["current_tag"], item["latest_tag"])
+        else:
+            logger.warning("No replacement made in %s for %s", item["file"], item["old_image"])
+    return changed
+
+
+def commit_and_push(repo_dir: str, changed: list[dict]) -> str:
+    """Stage changed files, commit, push. Returns the commit SHA."""
+    for item in changed:
+        _git(["add", item["file"]], cwd=repo_dir)
+
+    summary_lines = [f"- {item['image_short']}: {item['current_tag']} -> {item['latest_tag']}"
+                     for item in changed]
+    now = datetime.now(timezone.utc).strftime("%Y-%m-%d")
+    commit_msg = (
+        f"chore: upgrade {len(changed)} image(s) — {now}\n\n"
+        + "\n".join(summary_lines)
+    )
+    _git(["commit", "-m", commit_msg], cwd=repo_dir)
+    _git(["push", "origin", "main"], cwd=repo_dir)
+
+    sha = _git(["rev-parse", "--short", "HEAD"], cwd=repo_dir).stdout.strip()
+    logger.info("Pushed commit %s with %d image update(s)", sha, len(changed))
+    return sha
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Approval workflow
+# ─────────────────────────────────────────────────────────────────────────────
+
+def request_approval(upgrade_plan: list[dict]) -> str:
+    lines = ["Proposed ArgoCD image upgrades (GitOps — will commit to argocd-gitops):\n"]
+    for item in upgrade_plan:
+        lines.append(
+            f"- `{item['file']}` — `{item['image_short']}` "
+            f"`{item['current_tag']}` -> `{item['latest_tag']}`"
+        )
+    reason = "\n".join(lines)
+
+    resp = requests.post(
+        f"{APPROVAL_MIDDLEWARE_URL}/request-approval",
+        json={
+            "secret_path": "secret/approval-required/k8s-upgrades",
+            "requester": "k8s-version-tracker",
+            "reason": reason,
+            "ttl_minutes": APPROVAL_TIMEOUT_MINUTES,
+        },
+        timeout=15,
+    )
+    resp.raise_for_status()
+    approval_id = resp.json()["approval_id"]
+    logger.info("Approval request created: %s (TTL %dm)", approval_id, APPROVAL_TIMEOUT_MINUTES)
+    return approval_id
+
+
+def poll_for_decision(approval_id: str) -> str:
+    deadline = time.monotonic() + APPROVAL_TIMEOUT_MINUTES * 60
+    while time.monotonic() < deadline:
+        time.sleep(APPROVAL_POLL_INTERVAL)
+        try:
+            resp = requests.get(
+                f"{APPROVAL_MIDDLEWARE_URL}/approval/{approval_id}/status",
+                timeout=10,
+            )
+            if resp.status_code == 404:
+                return "expired"
+            resp.raise_for_status()
+            status = resp.json()["status"]
+            if status != "pending":
+                return status
+        except Exception as e:
+            logger.warning("Poll error (will retry): %s", e)
+    return "timeout"
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Mattermost notifications
+# ─────────────────────────────────────────────────────────────────────────────
+
+def send_mattermost(text: str) -> None:
+    requests.post(
+        MATTERMOST_WEBHOOK_URL,
+        json={"text": text, "username": "k8s-upgrade-bot", "icon_emoji": ":kubernetes:"},
+        timeout=15,
+    ).raise_for_status()
+
+
+def build_applied_report(changed: list[dict], sha: str) -> str:
+    now = datetime.now(timezone.utc).strftime("%Y-%m-%d %H:%M UTC")
+    lines = [
+        f"## :white_check_mark: K8s Image Upgrades Committed -- {now}\n",
+        f"Commit `{sha}` pushed to `argocd-gitops` — ArgoCD is syncing.\n",
+    ]
+    for item in sorted(changed, key=lambda x: x["file"]):
+        lines.append(
+            f"- `{item['file']}` **{item['image_short']}** "
+            f"`{item['current_tag']}` -> `{item['latest_tag']}`"
+        )
+    return "\n".join(lines)
+
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Main
+# ─────────────────────────────────────────────────────────────────────────────
+
+def main() -> None:
+    try:
+        config.load_incluster_config()
+    except config.ConfigException:
+        config.load_kube_config()
+
+    logger.info("Gathering cluster image inventory ...")
+    all_images = get_cluster_images()
+    logger.info("Found %d unique image references", len(all_images))
+
+    logger.info("Checking for outdated images ...")
+    outdated = collect_outdated(all_images)
+    logger.info("%d outdated image(s) found", len(outdated))
+
+    if not outdated:
+        logger.info("Nothing to upgrade.")
+        send_mattermost(
+            ":white_check_mark: **K8s Upgrade Check**: All images are current -- no upgrades needed."
+        )
+        return
+
+    # Clone repo early so we can build an accurate plan (which files will change)
+    repo_dir = tempfile.mkdtemp(prefix="argocd-gitops-")
+    try:
+        logger.info("Cloning gitops repo to build upgrade plan ...")
+        clone_repo(repo_dir)
+
+        upgrade_plan = build_upgrade_plan(repo_dir, outdated)
+
+        if not upgrade_plan:
+            msg_lines = [
+                f":warning: **K8s Upgrade Check**: {len(outdated)} outdated image(s) found "
+                "but none matched any YAML file in the gitops repo.\n",
+                "These may be images from Helm charts or external sources:",
+            ]
+            for entry in outdated:
+                msg_lines.append(
+                    f"- `{entry['image_short']}` `{entry['current_tag']}` -> `{entry['latest_tag']}`"
+                )
+            send_mattermost("\n".join(msg_lines))
+            return
+
+        logger.info(
+            "%d file update(s) planned across %d image(s) -- requesting approval ...",
+            len(upgrade_plan), len(outdated),
+        )
+        approval_id = request_approval(upgrade_plan)
+
+        logger.info(
+            "Polling for decision (timeout: %dm, interval: %ds) ...",
+            APPROVAL_TIMEOUT_MINUTES, APPROVAL_POLL_INTERVAL,
+        )
+        decision = poll_for_decision(approval_id)
+        logger.info("Decision: %s", decision)
+
+        if decision == "approved":
+            changed = apply_updates(upgrade_plan)
+            if changed:
+                sha = commit_and_push(repo_dir, changed)
+                report = build_applied_report(changed, sha)
+                send_mattermost(report)
+                logger.info("Done -- %d file(s) committed", len(changed))
+            else:
+                send_mattermost(
+                    ":warning: **K8s Upgrades**: Approval received but no file changes were "
+                    "produced (images may already be updated in the repo)."
+                )
+        else:
+            status_label = {"denied": "Denied", "expired": "Expired", "timeout": "Timed Out"}
+            emoji_map = {"denied": ":no_entry:", "expired": ":timer_clock:", "timeout": ":hourglass:"}
+            label = status_label.get(decision, decision.title())
+            icon = emoji_map.get(decision, ":warning:")
+            send_mattermost(
+                f"{icon} **K8s Upgrades {label}** -- no changes committed.\n"
+                f"{len(upgrade_plan)} file update(s) were proposed but not applied."
+            )
+            logger.info("No changes committed.")
+
+    finally:
+        shutil.rmtree(repo_dir, ignore_errors=True)
+
+
+if __name__ == "__main__":
+    main()
diff --git a/trigger-upgrade.sh b/trigger-upgrade.sh
new file mode 100755
index 0000000..18d7105
--- /dev/null
+++ b/trigger-upgrade.sh
@@ -0,0 +1,16 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+SSH_KEY="$(dirname "$0")/../../util/ssh-keys/id_rsa"
+CONTROL_PLANE="ubuntu@192.168.86.200"
+NAMESPACE="k8s-version-tracker"
+JOB_NAME="upgrade-manual-$(date +%Y%m%d-%H%M)"
+
+echo "Triggering upgrade-requester job: $JOB_NAME"
+ssh -i "$SSH_KEY" "$CONTROL_PLANE" \
+  "kubectl create job $JOB_NAME --from=cronjob/upgrade-requester -n $NAMESPACE"
+
+echo ""
+echo "Job created. Follow logs with:"
+echo "  ssh -i util/ssh-keys/id_rsa ubuntu@192.168.86.200 \\"
+echo "    \"kubectl logs -n $NAMESPACE -l job-name=$JOB_NAME -f\""