diff --git a/.github/workflows/pr-fast-ci.yml b/.github/workflows/pr-fast-ci.yml
index 9127082..22435b5 100644
--- a/.github/workflows/pr-fast-ci.yml
+++ b/.github/workflows/pr-fast-ci.yml
@@ -89,8 +89,14 @@ jobs:
         with:
           ref: ${{ github.event.pull_request.head.sha }}
 
-      - name: Run native app Swift tests
-        run: swift test --package-path native-app
+      - name: Run native app xcodebuild tests
+        working-directory: native-app
+        run: >-
+          xcodebuild
+          -scheme APW-Package
+          -destination 'platform=macOS'
+          -derivedDataPath .xcode-derived
+          test
 
   validate-secrets:
     name: Validate Secrets
diff --git a/docs/bootstrap/onboarding.md b/docs/bootstrap/onboarding.md
index 7ad2536..2b87a74 100644
--- a/docs/bootstrap/onboarding.md
+++ b/docs/bootstrap/onboarding.md
@@ -41,6 +41,7 @@
     - Docker, service-container, browser, and `container:` workloads stay on GitHub-hosted runners.
     - Keep PR checks cheap. Add heavy validation to `scripts/ci/run-extended-validation.sh` instead of the PR lane.
     - APW extended validation requires both Rust (`cargo`) and the macOS Swift toolchain, so the `extended-checks` job must run on the org macOS self-hosted pool (`[self-hosted, private, macOS, ARM64, xcode]`) rather than the Synology shell-only pool.
+    - Extended validation runs `scripts/ci/run-native-app-preflight.sh`, which exercises the Swift package through `xcodebuild`, builds `APW.app`, verifies codesign, and confirms the associated-domain entitlement is embedded.
     - Rust builds OpenSSL through the `openssl` crate's vendored feature, so the macOS runner needs source-build tools (`cc`, `make`, and `perl`) but does not require Homebrew, pkg-config, or a system OpenSSL prefix.
 
     ## Release Prep
diff --git a/native-app/APW.entitlements b/native-app/APW.entitlements
new file mode 100644
index 0000000..ed7f22a
--- /dev/null
+++ b/native-app/APW.entitlements
@@ -0,0 +1,10 @@
+<?xml version="1.0" encoding="UTF-8"?>
+<!DOCTYPE plist PUBLIC "-//Apple//DTD PLIST 1.0//EN" "http://www.apple.com/DTDs/PropertyList-1.0.dtd">
+<plist version="1.0">
+<dict>
+  <key>com.apple.developer.associated-domains</key>
+  <array>
+    <string>webcredentials:example.com</string>
+  </array>
+</dict>
+</plist>
diff --git a/scripts/build-native-app.sh b/scripts/build-native-app.sh
index d88ebff..337a8ad 100755
--- a/scripts/build-native-app.sh
+++ b/scripts/build-native-app.sh
@@ -12,6 +12,7 @@ MACOS_DIR="$CONTENTS_DIR/MacOS"
 RESOURCES_DIR="$CONTENTS_DIR/Resources"
 PLIST_PATH="$CONTENTS_DIR/Info.plist"
 EXECUTABLE_PATH="$PACKAGE_DIR/.build/release/$EXECUTABLE_NAME"
+ENTITLEMENTS_PATH="$PACKAGE_DIR/APW.entitlements"
 VERSION="$(awk -F ' = ' '$1 == "version" { gsub(/"/, "", $2); print $2; exit }' "$ROOT_DIR/rust/Cargo.toml")"
 
 if [[ -z "$VERSION" ]]; then
@@ -59,7 +60,7 @@ cat >"$PLIST_PATH" <<EOF
 EOF
 
 if command -v codesign >/dev/null 2>&1; then
-  if ! codesign -s - --force --deep "$APP_DIR" 2>/dev/null; then
+  if ! codesign -s - --force --deep --entitlements "$ENTITLEMENTS_PATH" "$APP_DIR" 2>/dev/null; then
     echo "Warning: ad-hoc code signing failed for $APP_DIR. The bundle may be rejected by Gatekeeper." >&2
   fi
 fi
diff --git a/scripts/ci/run-extended-validation.sh b/scripts/ci/run-extended-validation.sh
index 31aae44..88b16b0 100755
--- a/scripts/ci/run-extended-validation.sh
+++ b/scripts/ci/run-extended-validation.sh
@@ -50,6 +50,7 @@ fi
 
 require_tool cargo
 require_tool swift
+require_tool xcodebuild
 
 run_step "Rust native app end-to-end tests" \
   cargo test --manifest-path rust/Cargo.toml --test native_app_e2e
@@ -60,8 +61,8 @@ run_step "Rust security regression tests" \
 run_step "Rust clippy" \
   cargo clippy --manifest-path rust/Cargo.toml --all-targets -- -D warnings
 
-run_step "Swift native app release build" \
-  ./scripts/build-native-app.sh
+run_step "Native app xcodebuild, signing, and entitlement preflight" \
+  bash scripts/ci/run-native-app-preflight.sh
 
 echo
 echo "APW extended validation passed."
diff --git a/scripts/ci/run-fast-checks.sh b/scripts/ci/run-fast-checks.sh
index 46dacc7..557bb12 100755
--- a/scripts/ci/run-fast-checks.sh
+++ b/scripts/ci/run-fast-checks.sh
@@ -42,5 +42,6 @@ done < <(find .github/scripts scripts -type f -name '*.sh' -print0)
 
 ./scripts/test-render-homebrew-formula.sh
 ./scripts/test-extended-validation-config.sh
+./scripts/test-native-app-preflight-config.sh
 
 echo "APW fast checks passed."
diff --git a/scripts/ci/run-native-app-preflight.sh b/scripts/ci/run-native-app-preflight.sh
new file mode 100755
index 0000000..19a5cf2
--- /dev/null
+++ b/scripts/ci/run-native-app-preflight.sh
@@ -0,0 +1,71 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+ROOT_DIR="$(cd "$(dirname "${BASH_SOURCE[0]}")/../.." && pwd)"
+cd "$ROOT_DIR"
+
+require_tool() {
+  local tool="$1"
+  if ! command -v "$tool" >/dev/null 2>&1; then
+    echo "Missing required tool: $tool" >&2
+    exit 1
+  fi
+}
+
+if [[ "$(uname -s)" != "Darwin" ]]; then
+  echo "Native app preflight requires macOS." >&2
+  exit 1
+fi
+
+require_tool xcodebuild
+require_tool swift
+require_tool codesign
+require_tool plutil
+
+PLIST_BUDDY="/usr/libexec/PlistBuddy"
+if [[ ! -x "$PLIST_BUDDY" ]]; then
+  echo "Missing required tool: $PLIST_BUDDY" >&2
+  exit 1
+fi
+
+(
+  cd native-app
+  xcodebuild \
+    -scheme APW-Package \
+    -destination 'platform=macOS' \
+    -derivedDataPath .xcode-derived \
+    test
+)
+
+./scripts/build-native-app.sh >/dev/null
+
+app_dir="native-app/dist/APW.app"
+source_entitlements="native-app/APW.entitlements"
+entitlements_file="$(mktemp "${TMPDIR:-/tmp}/apw-entitlements.XXXXXX")"
+expected_domains_file="$(mktemp "${TMPDIR:-/tmp}/apw-expected-domains.XXXXXX")"
+actual_domains_file="$(mktemp "${TMPDIR:-/tmp}/apw-actual-domains.XXXXXX")"
+trap 'rm -f "$entitlements_file" "$expected_domains_file" "$actual_domains_file"' EXIT
+
+codesign --verify --deep --strict --verbose=2 "$app_dir"
+codesign -d --entitlements :- "$app_dir" >"$entitlements_file" 2>/dev/null
+
+if ! plutil -lint "$source_entitlements" >/dev/null; then
+  echo "APW source entitlements are not valid plist output." >&2
+  exit 1
+fi
+
+if ! plutil -lint "$entitlements_file" >/dev/null; then
+  echo "APW.app entitlements are not valid plist output." >&2
+  exit 1
+fi
+
+"$PLIST_BUDDY" -c "Print :com.apple.developer.associated-domains" "$source_entitlements" >"$expected_domains_file"
+"$PLIST_BUDDY" -c "Print :com.apple.developer.associated-domains" "$entitlements_file" >"$actual_domains_file"
+
+if ! cmp -s "$expected_domains_file" "$actual_domains_file"; then
+  echo "APW.app associated-domain entitlements differ from native-app/APW.entitlements." >&2
+  diff -u "$expected_domains_file" "$actual_domains_file" >&2 || true
+  exit 1
+fi
+
+echo "Native app xcodebuild, codesign, and entitlement preflight passed."
diff --git a/scripts/test-native-app-preflight-config.sh b/scripts/test-native-app-preflight-config.sh
new file mode 100755
index 0000000..6c8704b
--- /dev/null
+++ b/scripts/test-native-app-preflight-config.sh
@@ -0,0 +1,21 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+SCRIPT="scripts/ci/run-native-app-preflight.sh"
+
+require_line() {
+  local pattern="$1"
+  local message="$2"
+  if ! grep -Fq "$pattern" "$SCRIPT"; then
+    echo "$message" >&2
+    exit 1
+  fi
+}
+
+require_line "xcodebuild" "Native app preflight must run xcodebuild tests."
+require_line "codesign --verify --deep --strict" "Native app preflight must verify the signed app bundle."
+require_line "codesign -d --entitlements :-" "Native app preflight must extract embedded entitlements."
+require_line "Print :com.apple.developer.associated-domains" "Native app preflight must compare associated-domain entitlements."
+require_line "cmp -s \"\$expected_domains_file\" \"\$actual_domains_file\"" "Native app preflight must fail on entitlement drift."
+
+echo "Native app preflight contract test passed."