diff --git a/docs/wave/MIGRATION_DASHBOARD_SPEC.md b/docs/wave/MIGRATION_DASHBOARD_SPEC.md
index e928f44..c7f2aac 100644
--- a/docs/wave/MIGRATION_DASHBOARD_SPEC.md
+++ b/docs/wave/MIGRATION_DASHBOARD_SPEC.md
@@ -172,7 +172,15 @@ GitHub Issues/PRs (labels, state)
 ## Implementation Notes
 
 - The automated data pipeline is specified in W5-3B-AUTO-002 (dependency). This spec defines the data contract that pipeline must satisfy.
-- Until automation is available, maintainers can generate a manual snapshot using the GitHub Issues API:
+- Maintainers can generate milestone-specific health summaries with:
+  ```bash
+  ./scripts/gen-milestone-health-report.sh M5
+  ./scripts/gen-milestone-health-report.sh M6 kike-alt/DeWordle wave:5
+  ```
+- The generator writes both Markdown and JSON outputs under `docs/wave/`:
+  - `MILESTONE_HEALTH_<milestone>.md`
+  - `MILESTONE_HEALTH_<milestone>.json`
+- Until automation is available, maintainers can still generate a manual snapshot using the GitHub Issues API:
   ```bash
   gh issue list --label "Stellar Wave" --state all --json number,title,labels,state,assignees,milestone --limit 200 > docs/wave/dashboard-export.json
   ```
diff --git a/scripts/gen-milestone-health-report.sh b/scripts/gen-milestone-health-report.sh
new file mode 100755
index 0000000..013b936
--- /dev/null
+++ b/scripts/gen-milestone-health-report.sh
@@ -0,0 +1,209 @@
+#!/usr/bin/env bash
+# gen-milestone-health-report.sh
+# Generate milestone health summaries for Wave 5 maintainer triage.
+#
+# Usage:
+#   ./scripts/gen-milestone-health-report.sh <milestone> [repo] [label]
+#
+# Arguments:
+#   milestone  M3 | M4 | M5 | M6
+#   repo       owner/repo   (default: kike-alt/DeWordle)
+#   label      label name   (default: wave:5)
+#
+# Outputs:
+#   docs/wave/MILESTONE_HEALTH_<milestone>.md
+#   docs/wave/MILESTONE_HEALTH_<milestone>.json
+#
+# Requires:
+#   gh CLI authenticated
+#   jq
+
+set -euo pipefail
+
+MILESTONE="${1:-M5}"
+REPO="${2:-kike-alt/DeWordle}"
+LABEL_FILTER="${3:-wave:5}"
+OUTPUT_MD="docs/wave/MILESTONE_HEALTH_${MILESTONE}.md"
+OUTPUT_JSON="docs/wave/MILESTONE_HEALTH_${MILESTONE}.json"
+GENERATED_AT="$(date -u '+%Y-%m-%dT%H:%M:%SZ')"
+
+case "$MILESTONE" in
+  M3|M4|M5|M6) ;;
+  *)
+    echo "ERROR: milestone must be one of M3, M4, M5, M6 (got '$MILESTONE')" >&2
+    exit 1
+    ;;
+esac
+
+if ! command -v gh >/dev/null 2>&1; then
+  echo "ERROR: gh CLI is required but was not found in PATH" >&2
+  exit 1
+fi
+
+if ! command -v jq >/dev/null 2>&1; then
+  echo "ERROR: jq is required but was not found in PATH" >&2
+  exit 1
+fi
+
+echo "Fetching issues for milestone $MILESTONE from $REPO..."
+
+RAW_ISSUES="$(gh issue list \
+  --repo "$REPO" \
+  --milestone "$MILESTONE" \
+  --state all \
+  --json number,title,state,labels,assignees,milestone,createdAt,closedAt,url \
+  --limit 200)"
+
+FILTERED_ISSUES="$(printf '%s\n' "$RAW_ISSUES" | jq --arg label "$LABEL_FILTER" '
+  if $label == "" then
+    .
+  else
+    map(select(([.labels[].name] | index($label)) != null))
+  end
+')"
+
+REPORT_JSON="$(printf '%s\n' "$FILTERED_ISSUES" | jq --arg generatedAt "$GENERATED_AT" --arg repo "$REPO" --arg milestone "$MILESTONE" --arg label "$LABEL_FILTER" '
+  def normalize_state: (.state | ascii_downcase);
+  def label_names: [.labels[].name];
+  def first_label($prefix): ([label_names[] | select(startswith($prefix))][0] // null);
+  def is_blocked: ((label_names | index("blocked")) != null or (label_names | index("status:blocked")) != null);
+  def is_cross_track: ((label_names | index("cross-track")) != null);
+  def assignee_logins: [.assignees[].login];
+  def normalized_issues:
+    map({
+      number,
+      title,
+      url,
+      state: normalize_state,
+      createdAt,
+      closedAt,
+      labels: label_names,
+      assignees: assignee_logins,
+      track: ((first_label("track:") // "track:unlabeled") | sub("^track:"; "")),
+      blocked: is_blocked,
+      crossTrack: is_cross_track
+    });
+
+  normalized_issues as $issues |
+  {
+    generated_at: $generatedAt,
+    repo: $repo,
+    milestone: $milestone,
+    label_filter: ($label | if . == "" then null else . end),
+    summary: {
+      total: ($issues | length),
+      open: ($issues | map(select(.state == "open")) | length),
+      closed: ($issues | map(select(.state == "closed")) | length),
+      blocked_open: ($issues | map(select(.state == "open" and .blocked)) | length),
+      cross_track_total: ($issues | map(select(.crossTrack)) | length),
+      cross_track_open: ($issues | map(select(.state == "open" and .crossTrack)) | length)
+    },
+    track_summary: (
+      $issues
+      | group_by(.track)
+      | map({
+          track: .[0].track,
+          total: length,
+          open: (map(select(.state == "open")) | length),
+          closed: (map(select(.state == "closed")) | length),
+          blocked_open: (map(select(.state == "open" and .blocked)) | length),
+          cross_track_total: (map(select(.crossTrack)) | length)
+        })
+      | sort_by(.track)
+    ),
+    blocked_issues: (
+      $issues
+      | map(select(.state == "open" and .blocked))
+      | sort_by(.track, .number)
+    ),
+    cross_track_issues: (
+      $issues
+      | map(select(.crossTrack))
+      | sort_by(.state, .track, .number)
+    ),
+    issues: ($issues | sort_by(.state, .track, .number))
+  }
+')"
+
+printf '%s\n' "$REPORT_JSON" > "$OUTPUT_JSON"
+
+echo "Writing markdown summary to $OUTPUT_MD..."
+
+{
+  echo "# Milestone Health Report — $MILESTONE"
+  echo ""
+  echo "> Generated: $GENERATED_AT"
+  echo "> Repo: $REPO"
+  echo "> Milestone: $MILESTONE"
+  if [[ -n "$LABEL_FILTER" ]]; then
+    echo "> Label filter: \`$LABEL_FILTER\`"
+  else
+    echo "> Label filter: _none_"
+  fi
+  echo ""
+  echo "## Summary"
+  echo ""
+  printf '%s\n' "$REPORT_JSON" | jq -r '
+    .summary |
+    "- Total issues: \(.total)\n" +
+    "- Open: \(.open)\n" +
+    "- Closed: \(.closed)\n" +
+    "- Blocked (open): \(.blocked_open)\n" +
+    "- Cross-track (total): \(.cross_track_total)\n" +
+    "- Cross-track (open): \(.cross_track_open)"
+  '
+  echo ""
+  echo "## Track Breakdown"
+  echo ""
+  echo "| Track | Total | Open | Closed | Blocked (open) | Cross-track |"
+  echo "|---|---:|---:|---:|---:|---:|"
+  printf '%s\n' "$REPORT_JSON" | jq -r '
+    .track_summary[] |
+    "| \(.track) | \(.total) | \(.open) | \(.closed) | \(.blocked_open) | \(.cross_track_total) |"
+  '
+  echo ""
+  echo "## Blocked Issues"
+  echo ""
+  BLOCKED_COUNT="$(printf '%s\n' "$REPORT_JSON" | jq '.blocked_issues | length')"
+  if [[ "$BLOCKED_COUNT" -eq 0 ]]; then
+    echo "_No open blocked issues for this milestone/filter._"
+  else
+    printf '%s\n' "$REPORT_JSON" | jq -r '
+      .blocked_issues[] |
+      "- #\(.number) \(.title) — track: \(.track)" +
+      (if (.assignees | length) > 0 then " — assignees: " + (.assignees | join(", ")) else "" end)
+    '
+  fi
+  echo ""
+  echo "## Cross-Track Issues"
+  echo ""
+  CROSS_TRACK_COUNT="$(printf '%s\n' "$REPORT_JSON" | jq '.cross_track_issues | length')"
+  if [[ "$CROSS_TRACK_COUNT" -eq 0 ]]; then
+    echo "_No cross-track issues for this milestone/filter._"
+  else
+    printf '%s\n' "$REPORT_JSON" | jq -r '
+      .cross_track_issues[] |
+      "- #\(.number) \(.title) — state: \(.state) — track: \(.track)"
+    '
+  fi
+  echo ""
+  echo "## Issue Snapshot"
+  echo ""
+  echo "| Issue | State | Track | Blocked | Cross-track | Assignees | Title |"
+  echo "|---|---|---|---|---|---|---|"
+  printf '%s\n' "$REPORT_JSON" | jq -r '
+    .issues[] |
+    "| #\(.number) | \(.state) | \(.track) | " +
+    (if .blocked then "yes" else "no" end) +
+    " | " +
+    (if .crossTrack then "yes" else "no" end) +
+    " | " +
+    (if (.assignees | length) > 0 then (.assignees | join(", ")) else "—" end) +
+    " | " +
+    (.title | gsub("\\|"; "\\\\|")) +
+    " |"
+  '
+} > "$OUTPUT_MD"
+
+echo "JSON summary written to $OUTPUT_JSON"
+echo "Markdown summary written to $OUTPUT_MD"