diff --git a/.github/workflows/upstream-check.yaml b/.github/workflows/upstream-check.yaml
new file mode 100644
index 0000000..ab1852b
--- /dev/null
+++ b/.github/workflows/upstream-check.yaml
@@ -0,0 +1,32 @@
+name: Upstream Version Check
+
+on:
+  schedule:
+    # Run daily at 08:00 UTC.
+    - cron: '0 8 * * *'
+  workflow_dispatch:
+    inputs:
+      dry_run:
+        description: 'Preview changes without creating an issue'
+        type: boolean
+        default: false
+
+permissions:
+  issues: write
+
+jobs:
+  check-upstream:
+    name: Check Upstream Releases
+    runs-on: ubuntu-latest
+    steps:
+      - name: Checkout
+        uses: actions/checkout@v4
+
+      - name: Install yq
+        uses: mikefarah/yq@v4
+
+      - name: Run upstream check
+        run: ci/scripts/upstream-check.sh
+        env:
+          GH_TOKEN: ${{ secrets.GITHUB_TOKEN }}
+          DRY_RUN: ${{ inputs.dry_run || 'false' }}
diff --git a/.upstream-monitor.yaml b/.upstream-monitor.yaml
new file mode 100644
index 0000000..c1db149
--- /dev/null
+++ b/.upstream-monitor.yaml
@@ -0,0 +1,31 @@
+# Upstream Version Monitor Configuration
+#
+# Maps upstream product repositories to Helm chart artifacts.
+# The ci/scripts/upstream-check.sh script reads this file to detect
+# new upstream releases and open a GitHub issue when an update is available.
+#
+# Adding a new chart:
+#   1. Add a new entry under `charts:` with the chart path.
+#   2. List each upstream source with its GitHub repository.
+#   3. Define targets — which files and YAML paths hold the current version.
+#
+# Fields:
+#   name            — human-readable chart name (used in issue titles)
+#   path            — path to the chart directory relative to repo root
+#   sources[].name  — identifier for this upstream component
+#   sources[].github — GitHub owner/repo (used to query releases)
+#   sources[].strip_v_prefix — if true, strip leading "v" from the release
+#                     tag before comparing (e.g. "v0.65.3" → "0.65.3")
+#   sources[].targets[].file      — file holding current version, relative to chart path
+#   sources[].targets[].yaml_path — yq expression to the version field
+
+charts:
+  - name: netbird
+    path: charts/netbird
+    sources:
+      - name: server
+        github: netbirdio/netbird
+        strip_v_prefix: true
+        targets:
+          - file: Chart.yaml
+            yaml_path: .appVersion
diff --git a/CHANGELOG.md b/CHANGELOG.md
index 7f94038..80f7218 100644
--- a/CHANGELOG.md
+++ b/CHANGELOG.md
@@ -5,6 +5,24 @@ All notable changes to this project will be documented in this file.
 The format is based on [Keep a Changelog](https://keepachangelog.com/),
 and this project adheres to [Semantic Versioning](https://semver.org/).
 
+## Unreleased
+
+### Added
+
+- **Automated upstream version tracking**: New scheduled GitHub Actions workflow
+  (`.github/workflows/upstream-check.yaml`) that runs daily to detect new
+  releases from upstream repositories and opens a GitHub issue when an update
+  is available. Currently tracks NetBird server (`netbirdio/netbird`).
+- `.upstream-monitor.yaml` configuration file mapping upstream GitHub
+  repositories to Helm chart version fields. Add new charts or sources by
+  extending this file.
+- `ci/scripts/upstream-check.sh` script that reads the monitor config, queries
+  the GitHub API for latest releases, compares with current chart versions,
+  and creates GitHub issues for available updates. Supports `DRY_RUN=true`
+  for preview mode.
+- Workflow supports manual trigger via `workflow_dispatch` with optional
+  dry-run input.
+
 ## [0.1.1] — 2026-02-26
 
 ### Added
diff --git a/README.md b/README.md
index 30bc418..8e2143e 100644
--- a/README.md
+++ b/README.md
@@ -49,6 +49,54 @@ See each chart's README for detailed configuration.
 - [kubectl](https://kubernetes.io/docs/tasks/tools/) configured for your target cluster
 - Kubernetes 1.24+ (1.28+ for SQLite PAT seeding)
 
+## Automated Upstream Version Tracking
+
+A scheduled GitHub Actions workflow checks upstream repositories daily for new
+releases and opens a GitHub issue when a chart is behind upstream.
+
+### How It Works
+
+1. The workflow reads `.upstream-monitor.yaml` to discover which upstream repos
+   map to which chart version fields.
+2. For each source, it queries the GitHub Releases API for the latest non-draft,
+   non-prerelease tag.
+3. If the upstream version differs from what the chart currently references, a
+   GitHub issue is created with the current and latest versions, a link to the
+   upstream release, and a checklist of what needs to be done.
+
+### Configuration
+
+Edit `.upstream-monitor.yaml` to add new charts or upstream sources:
+
+```yaml
+charts:
+  - name: netbird
+    path: charts/netbird
+    sources:
+      - name: server
+        github: netbirdio/netbird
+        strip_v_prefix: true
+        targets:
+          - file: Chart.yaml
+            yaml_path: .appVersion
+```
+
+### Manual Trigger
+
+Run the check on demand from the Actions tab → **Upstream Version Check** →
+**Run workflow**. Enable the `dry_run` checkbox to preview changes without
+creating an issue.
+
+### Local Usage
+
+```bash
+# Preview what would change (no issue created)
+DRY_RUN=true ./ci/scripts/upstream-check.sh
+
+# Run for real (requires gh auth login)
+./ci/scripts/upstream-check.sh
+```
+
 ## Contributing
 
 We welcome contributions! Please read our [Contributing Guide](CONTRIBUTING.md) before submitting pull requests.
diff --git a/ci/scripts/upstream-check.sh b/ci/scripts/upstream-check.sh
new file mode 100755
index 0000000..a9c17fe
--- /dev/null
+++ b/ci/scripts/upstream-check.sh
@@ -0,0 +1,206 @@
+#!/usr/bin/env bash
+# upstream-check.sh — Detect new upstream releases and open GitHub issues.
+#
+# Reads .upstream-monitor.yaml, queries the GitHub API for latest releases,
+# and creates a GitHub issue when a chart is behind upstream.
+#
+# Required tools: yq (v4+), gh (GitHub CLI), jq
+#
+# Environment variables:
+#   GH_TOKEN   — GitHub token (set automatically in GitHub Actions)
+#   DRY_RUN    — "true" to skip issue creation (default: "false")
+#
+# Usage:
+#   ./ci/scripts/upstream-check.sh            # normal run
+#   DRY_RUN=true ./ci/scripts/upstream-check.sh   # preview only
+
+set -euo pipefail
+
+REPO_ROOT="$(git rev-parse --show-toplevel)"
+CONFIG_FILE="${REPO_ROOT}/.upstream-monitor.yaml"
+DRY_RUN="${DRY_RUN:-false}"
+
+# ── Helpers ───────────────────────────────────────────────────────────────
+
+log()  { echo "==> $*"; }
+info() { echo "    $*"; }
+warn() { echo "    WARNING: $*" >&2; }
+die()  { echo "ERROR: $*" >&2; exit 1; }
+
+check_deps() {
+  local missing=()
+  for cmd in yq gh jq; do
+    command -v "$cmd" &>/dev/null || missing+=("$cmd")
+  done
+  if [[ ${#missing[@]} -gt 0 ]]; then
+    die "missing required tools: ${missing[*]}"
+  fi
+}
+
+# Fetch the latest non-prerelease, non-draft release tag from a GitHub repo.
+get_latest_release_tag() {
+  local repo="$1"
+  gh api "repos/${repo}/releases/latest" --jq '.tag_name' 2>/dev/null || echo ""
+}
+
+# Fetch the URL of the latest release page.
+get_latest_release_url() {
+  local repo="$1"
+  gh api "repos/${repo}/releases/latest" --jq '.html_url' 2>/dev/null || echo ""
+}
+
+# Read a YAML field from a file.
+read_yaml() {
+  local file="$1" path="$2"
+  yq eval "$path" "$file"
+}
+
+# Check whether an open issue already exists with the given title.
+issue_exists_with_title() {
+  local title="$1"
+  local count
+  count=$(gh issue list --state open --search "$title" --json number,title \
+    --jq "[.[] | select(.title == \"$title\")] | length" 2>/dev/null || echo "0")
+  [[ "$count" -gt 0 ]]
+}
+
+# ── Main ──────────────────────────────────────────────────────────────────
+
+main() {
+  check_deps
+
+  if [[ ! -f "$CONFIG_FILE" ]]; then
+    die "config file not found: $CONFIG_FILE"
+  fi
+
+  local num_charts
+  num_charts=$(yq eval '.charts | length' "$CONFIG_FILE")
+
+  for ((i = 0; i < num_charts; i++)); do
+    local chart_name chart_rel_path chart_path
+    chart_name=$(yq eval ".charts[$i].name" "$CONFIG_FILE")
+    chart_rel_path=$(yq eval ".charts[$i].path" "$CONFIG_FILE")
+    chart_path="${REPO_ROOT}/${chart_rel_path}"
+
+    log "Chart: $chart_name ($chart_rel_path)"
+
+    if [[ ! -d "$chart_path" ]]; then
+      warn "chart directory not found: $chart_path — skipping"
+      continue
+    fi
+
+    local num_sources
+    num_sources=$(yq eval ".charts[$i].sources | length" "$CONFIG_FILE")
+
+    # Collect updates: each entry is "source_name|github_repo|file|yaml_path|old|new"
+    local updates=()
+
+    for ((j = 0; j < num_sources; j++)); do
+      local src_name github_repo strip_v
+      src_name=$(yq eval ".charts[$i].sources[$j].name" "$CONFIG_FILE")
+      github_repo=$(yq eval ".charts[$i].sources[$j].github" "$CONFIG_FILE")
+      strip_v=$(yq eval ".charts[$i].sources[$j].strip_v_prefix" "$CONFIG_FILE")
+
+      info "Source: $src_name ($github_repo)"
+
+      local latest_tag
+      latest_tag=$(get_latest_release_tag "$github_repo")
+      if [[ -z "$latest_tag" ]]; then
+        warn "could not fetch latest release for $github_repo — skipping"
+        continue
+      fi
+
+      local latest_version="$latest_tag"
+      if [[ "$strip_v" == "true" ]]; then
+        latest_version="${latest_tag#v}"
+      fi
+
+      local num_targets
+      num_targets=$(yq eval ".charts[$i].sources[$j].targets | length" "$CONFIG_FILE")
+
+      for ((k = 0; k < num_targets; k++)); do
+        local target_file yaml_path current_version
+        target_file=$(yq eval ".charts[$i].sources[$j].targets[$k].file" "$CONFIG_FILE")
+        yaml_path=$(yq eval ".charts[$i].sources[$j].targets[$k].yaml_path" "$CONFIG_FILE")
+        current_version=$(read_yaml "${chart_path}/${target_file}" "$yaml_path")
+
+        info "  ${target_file} (${yaml_path}): current=${current_version} latest=${latest_version}"
+
+        if [[ "$current_version" != "$latest_version" ]]; then
+          info "  UPDATE AVAILABLE: ${current_version} -> ${latest_version}"
+          updates+=("${src_name}|${github_repo}|${target_file}|${yaml_path}|${current_version}|${latest_version}")
+        else
+          info "  up to date"
+        fi
+      done
+    done
+
+    # ── No updates needed ──────────────────────────────────────────────
+    if [[ ${#updates[@]} -eq 0 ]]; then
+      log "No updates needed for $chart_name"
+      echo ""
+      continue
+    fi
+
+    # ── Build issue title and body ─────────────────────────────────────
+    local title_parts=()
+    local issue_body
+    issue_body="## Upstream Version Update Available"$'\n\n'
+    issue_body+="The following upstream component(s) for the **${chart_name}** chart have new releases:"$'\n\n'
+    issue_body+="| Component | Current Version | Latest Version | File | Field |"$'\n'
+    issue_body+="| --------- | --------------- | -------------- | ---- | ----- |"$'\n'
+
+    for entry in "${updates[@]}"; do
+      IFS='|' read -r src repo file path old new <<< "$entry"
+      title_parts+=("${src} ${old} → ${new}")
+      local release_url
+      release_url=$(get_latest_release_url "$repo")
+      if [[ -n "$release_url" ]]; then
+        issue_body+="| ${src} | \`${old}\` | [\`${new}\`](${release_url}) | \`${file}\` | \`${path}\` |"$'\n'
+      else
+        issue_body+="| ${src} | \`${old}\` | \`${new}\` | \`${file}\` | \`${path}\` |"$'\n'
+      fi
+    done
+
+    issue_body+=$'\n'"### What needs to be done"$'\n\n'
+    issue_body+="1. Update the version references listed above."$'\n'
+    issue_body+="2. Update any hardcoded version strings in test assertions (\`charts/${chart_name}/tests/\`)."$'\n'
+    issue_body+="3. Bump the chart version in \`Chart.yaml\`."$'\n'
+    issue_body+="4. Review the upstream release notes for breaking changes."$'\n'
+    issue_body+="5. Run \`make test\` to verify lint and unit tests pass."$'\n'
+    issue_body+=$'\n'"---"$'\n'
+    issue_body+="*This issue was created automatically by the upstream version checker.*"$'\n'
+
+    local joined_parts
+    joined_parts=$(printf '%s, ' "${title_parts[@]}")
+    joined_parts="${joined_parts%, }"
+    local issue_title="chore(${chart_name}): upstream update available — ${joined_parts}"
+
+    # ── Dry run ────────────────────────────────────────────────────────
+    if [[ "$DRY_RUN" == "true" ]]; then
+      log "DRY RUN — would create issue:"
+      info "Title: $issue_title"
+      echo "$issue_body"
+      echo ""
+      continue
+    fi
+
+    # ── Check for existing issue ───────────────────────────────────────
+    if issue_exists_with_title "$issue_title"; then
+      log "Issue already exists with title: $issue_title — skipping"
+      echo ""
+      continue
+    fi
+
+    # ── Create issue ───────────────────────────────────────────────────
+    gh issue create \
+      --title "$issue_title" \
+      --body "$issue_body" \
+      --label "autorelease"
+
+    log "Issue created for $chart_name"
+    echo ""
+  done
+}
+
+main "$@"