diff --git a/.woodpecker/edge-subpath.yml b/.woodpecker/edge-subpath.yml
new file mode 100644
index 0000000..2c11980
--- /dev/null
+++ b/.woodpecker/edge-subpath.yml
@@ -0,0 +1,317 @@
+# =============================================================================
+# .woodpecker/edge-subpath.yml — Edge subpath routing static checks
+#
+# Static validation for edge subpath routing configuration. This pipeline does
+# NOT run live service curls — it validates the configuration that would be
+# used by a deployed edge proxy.
+#
+# Checks:
+#   1. shellcheck — syntax check on tests/smoke-edge-subpath.sh
+#   2. caddy validate — validate the Caddyfile template syntax
+#   3. caddyfile-routing-test — verify Caddyfile routing block shape
+#   4. test-caddyfile-routing — run standalone unit test for Caddyfile structure
+#
+# Triggers:
+#   - Pull requests that modify edge-related files
+#
+# Environment variables (inherited from WOODPECKER_ENVIRONMENT):
+#   EDGE_BASE_URL      — Edge proxy URL for reference (default: http://localhost)
+#   EDGE_TIMEOUT       — Request timeout in seconds (default: 30)
+#   EDGE_MAX_RETRIES   — Max retries per request (default: 3)
+# =============================================================================
+
+when:
+  event: pull_request
+
+steps:
+  # ── 1. ShellCheck on smoke script ────────────────────────────────────────
+  # `shellcheck` validates bash syntax, style, and common pitfalls.
+  # Exit codes:
+  #   0 — all checks passed
+  #   1 — one or more issues found
+  - name: shellcheck-smoke
+    image: koalaman/shellcheck-alpine:stable
+    commands:
+      - shellcheck --severity=warning tests/smoke-edge-subpath.sh tests/test-caddyfile-routing.sh
+
+  # ── 2. Caddyfile template rendering ───────────────────────────────────────
+  # Render a mock Caddyfile for validation. The template uses Nomad's
+  # templating syntax ({{ range ... }}) which must be processed before Caddy
+  # can validate it. We render a mock version with Nomad templates expanded
+  # to static values for validation purposes.
+  - name: render-caddyfile
+    image: alpine:3.19
+    commands:
+      - apk add --no-cache coreutils
+      - |
+        set -e
+        mkdir -p edge-render
+        # Render mock Caddyfile with Nomad templates expanded
+        {
+          echo '# Caddyfile — edge proxy configuration (Nomad-rendered)'
+          echo '# Staging upstream discovered via Nomad service registration.'
+          echo ''
+          echo ':80 {'
+          echo '    # Redirect root to Forgejo'
+          echo '    handle / {'
+          echo '        redir /forge/ 302'
+          echo '    }'
+          echo ''
+          echo '    # Reverse proxy to Forgejo'
+          echo '    handle /forge/* {'
+          echo '        reverse_proxy 127.0.0.1:3000'
+          echo '    }'
+          echo ''
+          echo '    # Reverse proxy to Woodpecker CI'
+          echo '    handle /ci/* {'
+          echo '        reverse_proxy 127.0.0.1:8000'
+          echo '    }'
+          echo ''
+          echo '    # Reverse proxy to staging — dynamic port via Nomad service discovery'
+          echo '    handle /staging/* {'
+          echo '        reverse_proxy 127.0.0.1:8081'
+          echo '    }'
+          echo ''
+          echo '    # Chat service — reverse proxy to disinto-chat backend (#705)'
+          echo '    # OAuth routes bypass forward_auth — unauthenticated users need these (#709)'
+          echo '    handle /chat/login {'
+          echo '        reverse_proxy 127.0.0.1:8080'
+          echo '    }'
+          echo '    handle /chat/oauth/callback {'
+          echo '        reverse_proxy 127.0.0.1:8080'
+          echo '    }'
+          echo '    # Defense-in-depth: forward_auth stamps X-Forwarded-User from session (#709)'
+          echo '    handle /chat/* {'
+          echo '        forward_auth 127.0.0.1:8080 {'
+          echo '            uri /chat/auth/verify'
+          echo '            copy_headers X-Forwarded-User'
+          echo '            header_up X-Forward-Auth-Secret {$FORWARD_AUTH_SECRET}'
+          echo '        }'
+          echo '        reverse_proxy 127.0.0.1:8080'
+          echo '    }'
+          echo '}'
+        } > edge-render/Caddyfile
+        cp edge-render/Caddyfile edge-render/Caddyfile.rendered
+        echo "Caddyfile rendered successfully"
+
+  # ── 3. Caddy config validation ───────────────────────────────────────────
+  # `caddy validate` checks Caddyfile syntax and configuration.
+  # This validates the rendered Caddyfile against Caddy's parser.
+  # Exit codes:
+  #   0 — configuration is valid
+  #   1 — configuration has errors
+  - name: caddy-validate
+    image: alpine:3.19
+    commands:
+      - apk add --no-cache ca-certificates curl
+      - curl -sS -o /tmp/caddy "https://caddyserver.com/api/download?os=linux&arch=amd64"
+      - chmod +x /tmp/caddy
+      - /tmp/caddy version
+      - /tmp/caddy validate --config edge-render/Caddyfile.rendered --adapter caddyfile
+
+  # ── 4. Caddyfile routing block shape test ─────────────────────────────────
+  # Verify that the Caddyfile contains all required routing blocks:
+  #   - /forge/ — Forgejo subpath
+  #   - /ci/ — Woodpecker subpath
+  #   - /staging/ — Staging subpath
+  #   - /chat/ — Chat subpath with forward_auth
+  #
+  # This is a unit test that validates the expected structure without
+  # requiring a running Caddy instance.
+  - name: caddyfile-routing-test
+    image: alpine:3.19
+    commands:
+      - apk add --no-cache grep coreutils
+      - |
+        set -e
+
+        CADDYFILE="edge-render/Caddyfile.rendered"
+
+        echo "=== Validating Caddyfile routing blocks ==="
+
+        # Check that all required subpath handlers exist
+        # POSIX-safe loop (alpine /bin/sh has no arrays)
+        FAILED=0
+        for handler in "handle /forge/\*" "handle /ci/\*" "handle /staging/\*" "handle /chat/login" "handle /chat/oauth/callback" "handle /chat/\*"; do
+          if grep -q "$handler" "$CADDYFILE"; then
+            echo "[PASS] Found handler: $handler"
+          else
+            echo "[FAIL] Missing handler: $handler"
+            FAILED=1
+          fi
+        done
+
+        # Check forward_auth block exists for /chat/*
+        if grep -A5 "handle /chat/\*" "$CADDYFILE" | grep -q "forward_auth"; then
+          echo "[PASS] forward_auth block found for /chat/*"
+        else
+          echo "[FAIL] forward_auth block missing for /chat/*"
+          FAILED=1
+        fi
+
+        # Check reverse_proxy to Forgejo (port 3000)
+        if grep -q "reverse_proxy 127.0.0.1:3000" "$CADDYFILE"; then
+          echo "[PASS] Forgejo reverse_proxy configured (port 3000)"
+        else
+          echo "[FAIL] Forgejo reverse_proxy not configured"
+          FAILED=1
+        fi
+
+        # Check reverse_proxy to Woodpecker (port 8000)
+        if grep -q "reverse_proxy 127.0.0.1:8000" "$CADDYFILE"; then
+          echo "[PASS] Woodpecker reverse_proxy configured (port 8000)"
+        else
+          echo "[FAIL] Woodpecker reverse_proxy not configured"
+          FAILED=1
+        fi
+
+        # Check reverse_proxy to Chat (port 8080)
+        if grep -q "reverse_proxy 127.0.0.1:8080" "$CADDYFILE"; then
+          echo "[PASS] Chat reverse_proxy configured (port 8080)"
+        else
+          echo "[FAIL] Chat reverse_proxy not configured"
+          FAILED=1
+        fi
+
+        # Check root redirect to /forge/
+        if grep -q "redir /forge/ 302" "$CADDYFILE"; then
+          echo "[PASS] Root redirect to /forge/ configured"
+        else
+          echo "[FAIL] Root redirect to /forge/ not configured"
+          FAILED=1
+        fi
+
+        echo ""
+        if [ $FAILED -eq 0 ]; then
+          echo "=== All routing blocks validated ==="
+          exit 0
+        else
+          echo "=== Routing block validation failed ===" >&2
+          exit 1
+        fi
+
+  # ── 5. Standalone Caddyfile routing test ─────────────────────────────────
+  # Run the standalone unit test for Caddyfile routing block validation.
+  # This test extracts the Caddyfile template from edge.hcl and validates
+  # its structure without requiring a running Caddy instance.
+  - name: test-caddyfile-routing
+    image: alpine:3.19
+    commands:
+      - apk add --no-cache grep coreutils
+      - |
+        set -e
+        EDGE_TEMPLATE="nomad/jobs/edge.hcl"
+
+        echo "=== Extracting Caddyfile template from $EDGE_TEMPLATE ==="
+
+        # Extract the Caddyfile template (content between <<EOT and EOT markers)
+        CADDYFILE=$(sed -n '/data[[:space:]]*=[[:space:]]*<<[Ee][Oo][Tt]/,/^EOT$/p' "$EDGE_TEMPLATE" | sed '1s/.*/# Caddyfile extracted from Nomad template/; $d')
+
+        if [ -z "$CADDYFILE" ]; then
+          echo "ERROR: Could not extract Caddyfile template from $EDGE_TEMPLATE" >&2
+          exit 1
+        fi
+
+        echo "Caddyfile template extracted successfully"
+        echo ""
+
+        FAILED=0
+
+        # Check Forgejo subpath
+        if echo "$CADDYFILE" | grep -q "handle /forge/\*"; then
+          echo "[PASS] Forgejo handle block"
+        else
+          echo "[FAIL] Forgejo handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:3000"; then
+          echo "[PASS] Forgejo reverse_proxy (port 3000)"
+        else
+          echo "[FAIL] Forgejo reverse_proxy (port 3000)"
+          FAILED=1
+        fi
+
+        # Check Woodpecker subpath
+        if echo "$CADDYFILE" | grep -q "handle /ci/\*"; then
+          echo "[PASS] Woodpecker handle block"
+        else
+          echo "[FAIL] Woodpecker handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:8000"; then
+          echo "[PASS] Woodpecker reverse_proxy (port 8000)"
+        else
+          echo "[FAIL] Woodpecker reverse_proxy (port 8000)"
+          FAILED=1
+        fi
+
+        # Check Staging subpath
+        if echo "$CADDYFILE" | grep -q "handle /staging/\*"; then
+          echo "[PASS] Staging handle block"
+        else
+          echo "[FAIL] Staging handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "nomadService"; then
+          echo "[PASS] Staging Nomad service discovery"
+        else
+          echo "[FAIL] Staging Nomad service discovery"
+          FAILED=1
+        fi
+
+        # Check Chat subpath
+        if echo "$CADDYFILE" | grep -q "handle /chat/login"; then
+          echo "[PASS] Chat login handle block"
+        else
+          echo "[FAIL] Chat login handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "handle /chat/oauth/callback"; then
+          echo "[PASS] Chat OAuth callback handle block"
+        else
+          echo "[FAIL] Chat OAuth callback handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "handle /chat/\*"; then
+          echo "[PASS] Chat catch-all handle block"
+        else
+          echo "[FAIL] Chat catch-all handle block"
+          FAILED=1
+        fi
+
+        if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:8080"; then
+          echo "[PASS] Chat reverse_proxy (port 8080)"
+        else
+          echo "[FAIL] Chat reverse_proxy (port 8080)"
+          FAILED=1
+        fi
+
+        # Check forward_auth for chat
+        if echo "$CADDYFILE" | grep -A10 "handle /chat/\*" | grep -q "forward_auth"; then
+          echo "[PASS] forward_auth block for /chat/*"
+        else
+          echo "[FAIL] forward_auth block for /chat/*"
+          FAILED=1
+        fi
+
+        # Check root redirect
+        if echo "$CADDYFILE" | grep -q "redir /forge/ 302"; then
+          echo "[PASS] Root redirect to /forge/"
+        else
+          echo "[FAIL] Root redirect to /forge/"
+          FAILED=1
+        fi
+
+        echo ""
+        if [ $FAILED -eq 0 ]; then
+          echo "=== All routing blocks validated ==="
+          exit 0
+        else
+          echo "=== Routing block validation failed ===" >&2
+          exit 1
+        fi
diff --git a/tests/smoke-edge-subpath.sh b/tests/smoke-edge-subpath.sh
new file mode 100755
index 0000000..6a1f383
--- /dev/null
+++ b/tests/smoke-edge-subpath.sh
@@ -0,0 +1,310 @@
+#!/usr/bin/env bash
+# =============================================================================
+# smoke-edge-subpath.sh — End-to-end subpath routing smoke test
+#
+# Verifies Forgejo, Woodpecker, and chat function correctly under subpaths:
+#   - Forgejo at /forge/
+#   - Woodpecker at /ci/
+#   - Chat at /chat/
+#   - Staging at /staging/
+#
+# Usage:
+#   smoke-edge-subpath.sh [--base-url BASE_URL]
+#
+# Environment variables:
+#   BASE_URL         — Edge proxy URL (default: http://localhost)
+#   EDGE_TIMEOUT     — Request timeout in seconds (default: 30)
+#   EDGE_MAX_RETRIES — Max retries per request (default: 3)
+#
+# Exit codes:
+#   0 — All checks passed
+#   1 — One or more checks failed
+# =============================================================================
+set -euo pipefail
+
+# Script directory for relative paths
+SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+
+# Source common helpers if available
+source "${SCRIPT_DIR}/../lib/env.sh" 2>/dev/null || true
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Configuration
+# ─────────────────────────────────────────────────────────────────────────────
+
+BASE_URL="${BASE_URL:-http://localhost}"
+EDGE_TIMEOUT="${EDGE_TIMEOUT:-30}"
+EDGE_MAX_RETRIES="${EDGE_MAX_RETRIES:-3}"
+
+# Subpaths to test
+FORGE_PATH="/forge/"
+CI_PATH="/ci/"
+CHAT_PATH="/chat/"
+STAGING_PATH="/staging/"
+
+# Track overall test status
+FAILED=0
+PASSED=0
+SKIPPED=0
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Logging helpers
+# ─────────────────────────────────────────────────────────────────────────────
+
+log_info() {
+  echo "[INFO] $*"
+}
+
+log_pass() {
+  echo "[PASS] $*"
+  ((PASSED++)) || true
+}
+
+log_fail() {
+  echo "[FAIL] $*"
+  ((FAILED++)) || true
+}
+
+log_skip() {
+  echo "[SKIP] $*"
+  ((SKIPPED++)) || true
+}
+
+log_section() {
+  echo ""
+  echo "=== $* ==="
+  echo ""
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# HTTP helpers
+# ─────────────────────────────────────────────────────────────────────────────
+
+# Make an HTTP request with retry logic
+# Usage: http_request <method> <url> [options...]
+# Returns: HTTP status code on stdout
+http_request() {
+  local method="$1"
+  local url="$2"
+  shift 2
+
+  local retries=0
+  local response status
+
+  while [ "$retries" -lt "$EDGE_MAX_RETRIES" ]; do
+    response=$(curl -sS -w '\n%{http_code}' -X "$method" \
+      --max-time "$EDGE_TIMEOUT" \
+      -o /tmp/edge-response-$$ \
+      "$@" 2>&1) || {
+      retries=$((retries + 1))
+      log_info "Retry $retries/$EDGE_MAX_RETRIES for $url"
+      sleep 1
+      continue
+    }
+
+    status=$(echo "$response" | tail -n1)
+
+    echo "$status"
+    return 0
+  done
+
+  log_fail "Max retries exceeded for $url"
+  return 1
+}
+
+# Make a GET request and return status code
+http_get() {
+  local url="$1"
+  shift || true
+  http_request "GET" "$url" "$@"
+}
+
+# Make a HEAD request (no body)
+http_head() {
+  local url="$1"
+  shift || true
+  http_request "HEAD" "$url" "$@"
+}
+
+# Make a GET request and return the response body
+http_get_body() {
+  local url="$1"
+  shift || true
+  curl -sS --max-time "$EDGE_TIMEOUT" "$@" "$url"
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Test functions
+# ─────────────────────────────────────────────────────────────────────────────
+
+test_root_redirect() {
+  log_section "Test 1: Root redirect to /forge/"
+
+  local status
+  status=$(http_head "$BASE_URL/")
+
+  if [ "$status" = "302" ]; then
+    log_pass "Root / redirects with 302"
+  else
+    log_fail "Expected 302 redirect from /, got status $status"
+  fi
+}
+
+test_forgejo_subpath() {
+  log_section "Test 2: Forgejo at /forge/"
+
+  local status
+  status=$(http_head "$BASE_URL${FORGE_PATH}")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Forgejo at ${BASE_URL}${FORGE_PATH} returns status $status"
+  else
+    log_fail "Forgejo at ${BASE_URL}${FORGE_PATH} returned unexpected status $status"
+  fi
+}
+
+test_woodpecker_subpath() {
+  log_section "Test 3: Woodpecker at /ci/"
+
+  local status
+  status=$(http_head "$BASE_URL${CI_PATH}")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Woodpecker at ${BASE_URL}${CI_PATH} returns status $status"
+  else
+    log_fail "Woodpecker at ${BASE_URL}${CI_PATH} returned unexpected status $status"
+  fi
+}
+
+test_chat_subpath() {
+  log_section "Test 4: Chat at /chat/"
+
+  # Test chat login endpoint
+  local status
+  status=$(http_head "$BASE_URL${CHAT_PATH}login")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Chat login at ${BASE_URL}${CHAT_PATH}login returns status $status"
+  else
+    log_fail "Chat login at ${BASE_URL}${CHAT_PATH}login returned unexpected status $status"
+  fi
+
+  # Test chat OAuth callback endpoint
+  status=$(http_head "$BASE_URL${CHAT_PATH}oauth/callback")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Chat OAuth callback at ${BASE_URL}${CHAT_PATH}oauth/callback returns status $status"
+  else
+    log_fail "Chat OAuth callback at ${BASE_URL}${CHAT_PATH}oauth/callback returned unexpected status $status"
+  fi
+}
+
+test_staging_subpath() {
+  log_section "Test 5: Staging at /staging/"
+
+  local status
+  status=$(http_head "$BASE_URL${STAGING_PATH}")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Staging at ${BASE_URL}${STAGING_PATH} returns status $status"
+  else
+    log_fail "Staging at ${BASE_URL}${STAGING_PATH} returned unexpected status $status"
+  fi
+}
+
+test_forward_auth_rejection() {
+  log_section "Test 6: Forward auth on /chat/* rejects unauthenticated requests"
+
+  # Request a protected chat endpoint without auth header
+  # Should return 401 (Unauthorized) due to forward_auth
+  local status
+  status=$(http_head "$BASE_URL${CHAT_PATH}auth/verify")
+
+  if [ "$status" = "401" ]; then
+    log_pass "Unauthenticated /chat/auth/verify returns 401 (forward_auth working)"
+  elif [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_skip "Unauthenticated /chat/auth/verify returns $status (forward_auth may be disabled)"
+  else
+    log_fail "Expected 401 for unauthenticated /chat/auth/verify, got status $status"
+  fi
+}
+
+test_forgejo_oauth_callback() {
+  log_section "Test 7: Forgejo OAuth callback for Woodpecker under subpath"
+
+  # Test that Forgejo OAuth callback path works (Woodpecker OAuth integration)
+  local status
+  status=$(http_head "$BASE_URL${FORGE_PATH}login/oauth/callback")
+
+  if [ "$status" -ge 200 ] && [ "$status" -lt 400 ]; then
+    log_pass "Forgejo OAuth callback at ${BASE_URL}${FORGE_PATH}login/oauth/callback works"
+  else
+    log_fail "Forgejo OAuth callback returned unexpected status $status"
+  fi
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Main
+# ─────────────────────────────────────────────────────────────────────────────
+
+main() {
+  log_info "Starting subpath routing smoke test"
+  log_info "Base URL: $BASE_URL"
+  log_info "Timeout: ${EDGE_TIMEOUT}s, Max retries: ${EDGE_MAX_RETRIES}"
+
+  # Run all tests
+  test_root_redirect
+  test_forgejo_subpath
+  test_woodpecker_subpath
+  test_chat_subpath
+  test_staging_subpath
+  test_forward_auth_rejection
+  test_forgejo_oauth_callback
+
+  # Summary
+  log_section "Test Summary"
+  log_info "Passed: $PASSED"
+  log_info "Failed: $FAILED"
+  log_info "Skipped: $SKIPPED"
+
+  if [ "$FAILED" -gt 0 ]; then
+    log_fail "Some tests failed"
+    exit 1
+  fi
+
+  log_pass "All tests passed!"
+  exit 0
+}
+
+# Parse arguments
+while [[ $# -gt 0 ]]; do
+  case "$1" in
+    --base-url)
+      BASE_URL="$2"
+      shift 2
+      ;;
+    --base-url=*)
+      BASE_URL="${1#*=}"
+      shift
+      ;;
+    --help)
+      echo "Usage: $0 [options]"
+      echo ""
+      echo "Options:"
+      echo "  --base-url URL     Set base URL (default: http://localhost)"
+      echo "  --help             Show this help message"
+      echo ""
+      echo "Environment variables:"
+      echo "  BASE_URL           Base URL for edge proxy (default: http://localhost)"
+      echo "  EDGE_TIMEOUT       Request timeout in seconds (default: 30)"
+      echo "  EDGE_MAX_RETRIES   Max retries per request (default: 3)"
+      exit 0
+      ;;
+    *)
+      echo "Unknown option: $1" >&2
+      exit 1
+      ;;
+  esac
+done
+
+main
diff --git a/tests/test-caddyfile-routing.sh b/tests/test-caddyfile-routing.sh
new file mode 100755
index 0000000..52a7a3d
--- /dev/null
+++ b/tests/test-caddyfile-routing.sh
@@ -0,0 +1,231 @@
+#!/usr/bin/env bash
+# =============================================================================
+# test-caddyfile-routing.sh — Caddyfile routing block unit test
+#
+# Extracts the Caddyfile template from nomad/jobs/edge.hcl and validates its
+# structure without requiring a running Caddy instance.
+#
+# Checks:
+#   - Forgejo subpath (/forge/* -> :3000)
+#   - Woodpecker subpath (/ci/* -> :8000)
+#   - Staging subpath (/staging/* -> nomadService discovery)
+#   - Chat subpath (/chat/* with forward_auth and OAuth routes)
+#   - Root redirect to /forge/
+#
+# Usage:
+#   test-caddyfile-routing.sh
+#
+# Exit codes:
+#   0 — All checks passed
+#   1 — One or more checks failed
+# =============================================================================
+set -euo pipefail
+
+# Script directory for relative paths
+SCRIPT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")" && pwd)"
+REPO_ROOT="$(cd "${SCRIPT_DIR}/.." && pwd)"
+
+EDGE_TEMPLATE="${REPO_ROOT}/nomad/jobs/edge.hcl"
+
+# Track test status
+FAILED=0
+PASSED=0
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Logging helpers
+# ─────────────────────────────────────────────────────────────────────────────
+
+tr_info() {
+  echo "[INFO] $*"
+}
+
+tr_pass() {
+  echo "[PASS] $*"
+  ((PASSED++)) || true
+}
+
+tr_fail() {
+  echo "[FAIL] $*"
+  ((FAILED++)) || true
+}
+
+tr_section() {
+  echo ""
+  echo "=== $* ==="
+  echo ""
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Caddyfile extraction
+# ─────────────────────────────────────────────────────────────────────────────
+
+extract_caddyfile() {
+  local template_file="$1"
+
+  # Extract the Caddyfile template (content between <<EOT and EOT markers
+  # within the template stanza)
+  local caddyfile
+  caddyfile=$(sed -n '/data[[:space:]]*=[[:space:]]*<<[Ee][Oo][Tt]/,/^EOT$/p' "$template_file" | sed '1s/.*/# Caddyfile extracted from Nomad template/; $d')
+
+  if [ -z "$caddyfile" ]; then
+    echo "ERROR: Could not extract Caddyfile template from $template_file" >&2
+    return 1
+  fi
+
+  echo "$caddyfile"
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Validation functions
+# ─────────────────────────────────────────────────────────────────────────────
+
+check_forgejo_routing() {
+  tr_section "Validating Forgejo routing"
+
+  # Check handle block for /forge/*
+  if echo "$CADDYFILE" | grep -q "handle /forge/\*"; then
+    tr_pass "Forgejo handle block (handle /forge/*)"
+  else
+    tr_fail "Missing Forgejo handle block (handle /forge/*)"
+  fi
+
+  # Check reverse_proxy to Forgejo on port 3000
+  if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:3000"; then
+    tr_pass "Forgejo reverse_proxy configured (127.0.0.1:3000)"
+  else
+    tr_fail "Missing Forgejo reverse_proxy (127.0.0.1:3000)"
+  fi
+}
+
+check_woodpecker_routing() {
+  tr_section "Validating Woodpecker routing"
+
+  # Check handle block for /ci/*
+  if echo "$CADDYFILE" | grep -q "handle /ci/\*"; then
+    tr_pass "Woodpecker handle block (handle /ci/*)"
+  else
+    tr_fail "Missing Woodpecker handle block (handle /ci/*)"
+  fi
+
+  # Check reverse_proxy to Woodpecker on port 8000
+  if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:8000"; then
+    tr_pass "Woodpecker reverse_proxy configured (127.0.0.1:8000)"
+  else
+    tr_fail "Missing Woodpecker reverse_proxy (127.0.0.1:8000)"
+  fi
+}
+
+check_staging_routing() {
+  tr_section "Validating Staging routing"
+
+  # Check handle block for /staging/*
+  if echo "$CADDYFILE" | grep -q "handle /staging/\*"; then
+    tr_pass "Staging handle block (handle /staging/*)"
+  else
+    tr_fail "Missing Staging handle block (handle /staging/*)"
+  fi
+
+  # Check for nomadService discovery (dynamic port)
+  if echo "$CADDYFILE" | grep -q "nomadService"; then
+    tr_pass "Staging uses Nomad service discovery"
+  else
+    tr_fail "Missing Nomad service discovery for staging"
+  fi
+}
+
+check_chat_routing() {
+  tr_section "Validating Chat routing"
+
+  # Check login endpoint
+  if echo "$CADDYFILE" | grep -q "handle /chat/login"; then
+    tr_pass "Chat login handle block (handle /chat/login)"
+  else
+    tr_fail "Missing Chat login handle block (handle /chat/login)"
+  fi
+
+  # Check OAuth callback endpoint
+  if echo "$CADDYFILE" | grep -q "handle /chat/oauth/callback"; then
+    tr_pass "Chat OAuth callback handle block (handle /chat/oauth/callback)"
+  else
+    tr_fail "Missing Chat OAuth callback handle block (handle /chat/oauth/callback)"
+  fi
+
+  # Check catch-all for /chat/*
+  if echo "$CADDYFILE" | grep -q "handle /chat/\*"; then
+    tr_pass "Chat catch-all handle block (handle /chat/*)"
+  else
+    tr_fail "Missing Chat catch-all handle block (handle /chat/*)"
+  fi
+
+  # Check reverse_proxy to Chat on port 8080
+  if echo "$CADDYFILE" | grep -q "reverse_proxy 127.0.0.1:8080"; then
+    tr_pass "Chat reverse_proxy configured (127.0.0.1:8080)"
+  else
+    tr_fail "Missing Chat reverse_proxy (127.0.0.1:8080)"
+  fi
+
+  # Check forward_auth block for /chat/*
+  if echo "$CADDYFILE" | grep -A10 "handle /chat/\*" | grep -q "forward_auth"; then
+    tr_pass "forward_auth block configured for /chat/*"
+  else
+    tr_fail "Missing forward_auth block for /chat/*"
+  fi
+
+  # Check forward_auth URI
+  if echo "$CADDYFILE" | grep -q "uri /chat/auth/verify"; then
+    tr_pass "forward_auth URI configured (/chat/auth/verify)"
+  else
+    tr_fail "Missing forward_auth URI (/chat/auth/verify)"
+  fi
+}
+
+check_root_redirect() {
+  tr_section "Validating root redirect"
+
+  # Check root redirect to /forge/
+  if echo "$CADDYFILE" | grep -q "redir /forge/ 302"; then
+    tr_pass "Root redirect to /forge/ configured (302)"
+  else
+    tr_fail "Missing root redirect to /forge/"
+  fi
+}
+
+# ─────────────────────────────────────────────────────────────────────────────
+# Main
+# ─────────────────────────────────────────────────────────────────────────────
+
+main() {
+  tr_info "Extracting Caddyfile template from $EDGE_TEMPLATE"
+
+  # Extract Caddyfile
+  CADDYFILE=$(extract_caddyfile "$EDGE_TEMPLATE")
+
+  if [ -z "$CADDYFILE" ]; then
+    tr_fail "Could not extract Caddyfile template"
+    exit 1
+  fi
+
+  tr_pass "Caddyfile template extracted successfully"
+
+  # Run all validation checks
+  check_forgejo_routing
+  check_woodpecker_routing
+  check_staging_routing
+  check_chat_routing
+  check_root_redirect
+
+  # Summary
+  tr_section "Test Summary"
+  tr_info "Passed: $PASSED"
+  tr_info "Failed: $FAILED"
+
+  if [ "$FAILED" -gt 0 ]; then
+    tr_fail "Some checks failed"
+    exit 1
+  fi
+
+  tr_pass "All routing blocks validated!"
+  exit 0
+}
+
+main