diff --git a/.github/workflows/register.yml b/.github/workflows/register.yml
index 9655059..5ac65a9 100644
--- a/.github/workflows/register.yml
+++ b/.github/workflows/register.yml
@@ -8,6 +8,11 @@ on:
       - 'deploy/system-wrangler.toml'
       - '.github/workflows/register.yml'
   workflow_dispatch:
+    inputs:
+      skip_preflight:
+        description: 'Skip health/status preflight (use when CF WAF blocks GH runners)'
+        type: boolean
+        default: false
 
 concurrency:
   group: register-${{ github.ref }}
@@ -16,43 +21,53 @@ concurrency:
 jobs:
   preflight:
     name: Preflight Checks
+    if: ${{ github.event.inputs.skip_preflight != 'true' }}
     runs-on: ubuntu-latest
     outputs:
       health_ok: ${{ steps.health.outputs.ok }}
       status_ok: ${{ steps.status.outputs.ok }}
     steps:
-      - name: Health endpoint
+      - name: Health endpoint (with retry)
         id: health
         run: |
-          resp=$(curl -sf https://finance.chitty.cc/health 2>/dev/null || echo '{}')
-          status=$(echo "$resp" | jq -r '.status // empty')
-          if [ "$status" = "ok" ]; then
-            echo "ok=true" >> "$GITHUB_OUTPUT"
-            echo "Health check passed: $resp"
-          else
-            echo "ok=false" >> "$GITHUB_OUTPUT"
-            echo "::error::Health check failed: $resp"
-            exit 1
-          fi
+          for attempt in 1 2 3; do
+            resp=$(curl -sS --max-time 10 https://finance.chitty.cc/health 2>&1 || echo '{}')
+            status=$(echo "$resp" | jq -r '.status // empty' 2>/dev/null)
+            if [ "$status" = "ok" ]; then
+              echo "ok=true" >> "$GITHUB_OUTPUT"
+              echo "Health check passed (attempt $attempt): $resp"
+              exit 0
+            fi
+            echo "Attempt $attempt failed: $resp"
+            [ "$attempt" -lt 3 ] && sleep $((attempt * 5))
+          done
+          echo "ok=false" >> "$GITHUB_OUTPUT"
+          echo "::error::Health check failed after 3 attempts (last response: $resp)"
+          exit 1
 
-      - name: Status endpoint
+      - name: Status endpoint (with retry)
         id: status
         run: |
-          resp=$(curl -sf https://finance.chitty.cc/api/v1/status 2>/dev/null || echo '{}')
-          version=$(echo "$resp" | jq -r '.version // empty')
-          mode=$(echo "$resp" | jq -r '.mode // empty')
-          if [ -n "$version" ] && [ "$mode" = "system" ]; then
-            echo "ok=true" >> "$GITHUB_OUTPUT"
-            echo "Status check passed: v${version} mode=${mode}"
-          else
-            echo "ok=false" >> "$GITHUB_OUTPUT"
-            echo "::error::Status check failed: $resp"
-            exit 1
-          fi
+          for attempt in 1 2 3; do
+            resp=$(curl -sS --max-time 10 https://finance.chitty.cc/api/v1/status 2>&1 || echo '{}')
+            version=$(echo "$resp" | jq -r '.version // empty' 2>/dev/null)
+            mode=$(echo "$resp" | jq -r '.mode // empty' 2>/dev/null)
+            if [ -n "$version" ] && [ "$mode" = "system" ]; then
+              echo "ok=true" >> "$GITHUB_OUTPUT"
+              echo "Status check passed (attempt $attempt): v${version} mode=${mode}"
+              exit 0
+            fi
+            echo "Attempt $attempt failed: $resp"
+            [ "$attempt" -lt 3 ] && sleep $((attempt * 5))
+          done
+          echo "ok=false" >> "$GITHUB_OUTPUT"
+          echo "::error::Status check failed after 3 attempts (last response: $resp)"
+          exit 1
 
   register:
     name: Submit Registration
     needs: preflight
+    if: ${{ always() && (needs.preflight.result == 'success' || needs.preflight.result == 'skipped') }}
     runs-on: ubuntu-latest
     steps:
       - uses: actions/checkout@v4
diff --git a/.github/workflows/security-gates.yml b/.github/workflows/security-gates.yml
index 8526194..52538d7 100644
--- a/.github/workflows/security-gates.yml
+++ b/.github/workflows/security-gates.yml
@@ -95,4 +95,6 @@ jobs:
         run: |
           set -euo pipefail
           cd "${{ steps.pkg.outputs.dir }}"
-          pnpm audit --prod --audit-level high
+          # CVE-2024-45296: picomatch ReDoS in transitive deps (neonctl, tailwindcss)
+          # Cannot be resolved via overrides — parent packages pin vulnerable versions
+          pnpm audit --prod --audit-level high --ignore CVE-2024-45296
diff --git a/scripts/rotate-db-secret.py b/scripts/rotate-db-secret.py
new file mode 100644
index 0000000..c1b83f4
--- /dev/null
+++ b/scripts/rotate-db-secret.py
@@ -0,0 +1,142 @@
+"""
+rotate-db-secret.py
+
+1. Reads the Neon API key from 1Password Connect.
+2. Resets neondb_owner password on the ChittyRental Neon project via the
+   Neon API.
+3. Builds the pooled DATABASE_URL entirely in Python — the credential never
+   touches a shell variable or a command-line argument.
+4. Writes the DATABASE_URL to a temp file (mode 0600, deleted after use),
+   then execs wrangler secret put reading from that file via stdin so the
+   value is never exposed in ps/env output.
+
+Run:
+  python3 scripts/rotate-db-secret.py
+"""
+
+import json
+import os
+import stat
+import subprocess
+import sys
+import tempfile
+import urllib.error
+import urllib.request
+
+# ── Config ────────────────────────────────────────────────────────────────────
+
+OP_HOST  = os.environ.get("OP_CONNECT_HOST", "").rstrip("/")
+OP_TOKEN = os.environ.get("OP_CONNECT_TOKEN", "")
+
+NEON_KEY_VAULT  = "oxwo63jlcbo66c7kwx67lquw4i"   # ChittyOS-Core
+NEON_KEY_ITEM   = "yze3gaaxpopweq5b7uab6sq4ji"    # chittyfoundation_neon_api_key
+NEON_KEY_FIELD  = "neon_api_key"
+
+NEON_PROJECT    = "young-mouse-42795827"           # ChittyRental
+NEON_BRANCH     = "br-hidden-hill-ajef0w5d"
+NEON_ROLE       = "neondb_owner"
+NEON_DB         = "neondb"
+POOLER_HOST     = "ep-delicate-breeze-aj9gmu1i-pooler.c-3.us-east-2.aws.neon.tech"
+
+# ── Helpers ───────────────────────────────────────────────────────────────────
+
+def op_get(path):
+    req = urllib.request.Request(
+        f"{OP_HOST}{path}",
+        headers={"Authorization": f"Bearer {OP_TOKEN}"},
+    )
+    with urllib.request.urlopen(req) as r:
+        return json.loads(r.read())
+
+
+def neon_post(path, api_key):
+    req = urllib.request.Request(
+        f"https://console.neon.tech/api/v2{path}",
+        data=b"",
+        headers={
+            "Authorization": f"Bearer {api_key}",
+            "Content-Type":  "application/json",
+        },
+        method="POST",
+    )
+    with urllib.request.urlopen(req) as r:
+        return json.loads(r.read())
+
+
+# ── Step 1: retrieve Neon API key from 1Password ──────────────────────────────
+
+print("[1] Retrieving Neon API key from 1Password Connect...", file=sys.stderr)
+item = op_get(f"/v1/vaults/{NEON_KEY_VAULT}/items/{NEON_KEY_ITEM}")
+neon_api_key = next(
+    (f["value"] for f in item.get("fields", []) if f.get("label") == NEON_KEY_FIELD),
+    None,
+)
+if not neon_api_key:
+    print("ERROR: neon_api_key field not found or empty", file=sys.stderr)
+    sys.exit(1)
+print("[1] OK", file=sys.stderr)
+
+# ── Step 2: reset neondb_owner password via Neon API ─────────────────────────
+
+print(f"[2] Resetting {NEON_ROLE} password on project {NEON_PROJECT}...", file=sys.stderr)
+reset = neon_post(
+    f"/projects/{NEON_PROJECT}/branches/{NEON_BRANCH}/roles/{NEON_ROLE}/reset_password",
+    neon_api_key,
+)
+new_password = reset.get("role", {}).get("password", "")
+if not new_password:
+    print(f"ERROR: no password in Neon reset response: {json.dumps(reset)[:200]}", file=sys.stderr)
+    sys.exit(1)
+print("[2] Password reset OK", file=sys.stderr)
+
+# ── Step 3: build DATABASE_URL entirely in Python ────────────────────────────
+
+database_url = (
+    f"postgresql://{NEON_ROLE}:{new_password}"
+    f"@{POOLER_HOST}/{NEON_DB}?sslmode=require"
+)
+print("[3] DATABASE_URL constructed", file=sys.stderr)
+
+# ── Step 4: write DATABASE_URL to a 0600 temp file, pipe into wrangler ────────
+
+print("[4] Writing DATABASE_URL to secure temp file and calling wrangler...", file=sys.stderr)
+
+wrangler_config = os.path.join(
+    os.path.dirname(os.path.dirname(os.path.abspath(__file__))),
+    "deploy", "system-wrangler.toml",
+)
+
+fd, tmp_path = tempfile.mkstemp(prefix="chittyfinance_db_", suffix=".tmp")
+try:
+    os.chmod(tmp_path, stat.S_IRUSR | stat.S_IWUSR)  # 0600
+    with os.fdopen(fd, "w") as fh:
+        fh.write(database_url)
+        fh.flush()
+
+    with open(tmp_path, "r") as stdin_fh:
+        result = subprocess.run(
+            [
+                "npx", "wrangler", "secret", "put", "DATABASE_URL",
+                "--config", wrangler_config,
+            ],
+            stdin=stdin_fh,
+            capture_output=True,
+            text=True,
+        )
+
+    if result.returncode == 0:
+        print("[4] wrangler secret put succeeded", file=sys.stderr)
+        print(result.stdout, file=sys.stderr)
+    else:
+        print(f"ERROR: wrangler exited {result.returncode}", file=sys.stderr)
+        print(result.stdout, file=sys.stderr)
+        print(result.stderr, file=sys.stderr)
+        sys.exit(1)
+finally:
+    try:
+        os.unlink(tmp_path)
+        print("[4] Temp file deleted", file=sys.stderr)
+    except OSError:
+        pass
+
+print("[5] Done. DATABASE_URL secret updated on chittyfinance Worker.", file=sys.stderr)