diff --git a/.buildkite/commands/build-wda.sh b/.buildkite/commands/build-wda.sh
new file mode 100755
index 000000000000..5b079b0c6c30
--- /dev/null
+++ b/.buildkite/commands/build-wda.sh
@@ -0,0 +1,69 @@
+#!/usr/bin/env bash
+# Clone and build WebDriverAgent for iOS Simulator testing.
+#
+# Skips the build only when a usable build-for-testing artifact already exists.
+#
+# Required (one of):
+#   SIMULATOR_UDID  Simulator UDID for the build destination
+#   SIMULATOR_NAME  Simulator name for the build destination (e.g., iPhone 16)
+#
+# Optional:
+#   WEBDRIVERAGENT_REPO_URL  Repo URL (default: appium/WebDriverAgent)
+#   WEBDRIVERAGENT_REF       Git ref or commit to build (default: current remote HEAD / existing checkout)
+
+set -euo pipefail
+
+if [[ -z "${SIMULATOR_UDID:-}" && -z "${SIMULATOR_NAME:-}" ]]; then
+  echo "Error: set SIMULATOR_UDID or SIMULATOR_NAME" >&2
+  exit 1
+fi
+
+WDA_DIR=".build/WebDriverAgent"
+WDA_PROJECT="${WDA_DIR}/WebDriverAgent.xcodeproj"
+WDA_DERIVED_DATA="${WDA_DIR}/DerivedData"
+WEBDRIVERAGENT_REPO_URL="${WEBDRIVERAGENT_REPO_URL:-https://github.com/appium/WebDriverAgent.git}"
+WEBDRIVERAGENT_REF="${WEBDRIVERAGENT_REF:-}"
+
+if [[ -n "${SIMULATOR_UDID:-}" ]]; then
+  DESTINATION="platform=iOS Simulator,id=${SIMULATOR_UDID}"
+else
+  DESTINATION="platform=iOS Simulator,name=${SIMULATOR_NAME}"
+fi
+
+ensure_wda_checkout() {
+  mkdir -p .build
+
+  if [[ ! -d "${WDA_DIR}/.git" ]]; then
+    git clone --depth 1 "${WEBDRIVERAGENT_REPO_URL}" "${WDA_DIR}"
+  fi
+
+  if [[ -n "${WEBDRIVERAGENT_REF}" ]]; then
+    git -C "${WDA_DIR}" fetch --depth 1 origin "${WEBDRIVERAGENT_REF}"
+    git -C "${WDA_DIR}" checkout --detach "${WEBDRIVERAGENT_REF}"
+  fi
+}
+
+has_built_artifacts() {
+  [[ -d "${WDA_DERIVED_DATA}/Build/Products" ]] && \
+    find "${WDA_DERIVED_DATA}/Build/Products" -name '*.xctestrun' -print -quit | grep -q .
+}
+
+ensure_wda_checkout
+
+if [[ -d "$WDA_PROJECT" ]] && has_built_artifacts; then
+  echo "WebDriverAgent already built, skipping."
+  exit 0
+fi
+
+xcodebuild build-for-testing \
+  -project "$WDA_PROJECT" \
+  -scheme WebDriverAgentRunner \
+  -destination "$DESTINATION" \
+  -derivedDataPath "$WDA_DERIVED_DATA" \
+  CODE_SIGNING_ALLOWED=NO \
+  | tail -1
+
+if ! has_built_artifacts; then
+  echo "Error: WebDriverAgent build completed without an .xctestrun artifact" >&2
+  exit 1
+fi
diff --git a/.buildkite/commands/run-ai-e2e-tests.sh b/.buildkite/commands/run-ai-e2e-tests.sh
new file mode 100755
index 000000000000..21a03fde6c6c
--- /dev/null
+++ b/.buildkite/commands/run-ai-e2e-tests.sh
@@ -0,0 +1,147 @@
+#!/usr/bin/env bash
+# Run AI-driven E2E tests on an iOS Simulator using simulator-llm-pilot.
+#
+# This script manages the full lifecycle:
+#   1. Check for "Testing" label on PR (Buildkite only, skips if missing)
+#   2. Download build artifacts and install app (Buildkite only)
+#   3. Install the simulator-llm-pilot gem from GitHub
+#   4. Run tests (gem handles simulator, WDA, agent loop, and results)
+#
+# The gem provides a sandboxed agent that drives the simulator through a
+# fixed set of tools (tap, swipe, type, REST API, etc.) — no arbitrary
+# code execution, no shell access.
+#
+# Required environment variables:
+#   ANTHROPIC_API_KEY                  Claude API key
+#   SIMULATOR_LLM_PILOT_SITE_URL      WordPress test site URL
+#   SIMULATOR_LLM_PILOT_USERNAME      WordPress username
+#   SIMULATOR_LLM_PILOT_APP_PASSWORD  WordPress application password
+#
+# Optional environment variables:
+#   APP                            wordpress | jetpack (default: jetpack)
+#   SIMULATOR_NAME                 Simulator to boot if none running (default: iPhone 16)
+#   TEST_DIR                       Test directory (default: Tests/AgentTests/ui-tests)
+#   SIMULATOR_LLM_PILOT_REPO_URL   Remote repo URL for simulator-llm-pilot
+#   SIMULATOR_LLM_PILOT_SOURCE_PATH Local source checkout override for simulator-llm-pilot
+
+set -euo pipefail
+
+SCRIPT_DIR="$(cd "$(dirname "$0")" && pwd)"
+REPO_ROOT="$(cd "$SCRIPT_DIR/../.." && pwd)"
+cd "$REPO_ROOT"
+
+normalize_site_url() {
+  local site_url="$1"
+  if [[ "$site_url" == http://* || "$site_url" == https://* ]]; then
+    printf '%s' "$site_url"
+  else
+    printf 'https://%s' "$site_url"
+  fi
+}
+
+# ── Label gate (Buildkite only) ─────────────────────────────────────
+if [[ -n "${BUILDKITE_PULL_REQUEST_LABELS:-}" ]]; then
+  echo "--- Checking for 'Testing' label"
+
+  if ! echo ",${BUILDKITE_PULL_REQUEST_LABELS}," | grep -qF ",Testing,"; then
+    echo "PR does not have the 'Testing' label. Skipping."
+    echo "Add the label and re-run this step to trigger AI E2E tests."
+    exit 0
+  fi
+  echo "'Testing' label found."
+fi
+
+# ── Required env vars ────────────────────────────────────────────────
+: "${ANTHROPIC_API_KEY:?Set ANTHROPIC_API_KEY}"
+: "${SIMULATOR_LLM_PILOT_SITE_URL:?Set SIMULATOR_LLM_PILOT_SITE_URL}"
+: "${SIMULATOR_LLM_PILOT_USERNAME:?Set SIMULATOR_LLM_PILOT_USERNAME}"
+: "${SIMULATOR_LLM_PILOT_APP_PASSWORD:?Set SIMULATOR_LLM_PILOT_APP_PASSWORD}"
+export SIMULATOR_LLM_PILOT_SITE_URL="$(normalize_site_url "$SIMULATOR_LLM_PILOT_SITE_URL")"
+
+# ── Defaults ─────────────────────────────────────────────────────────
+APP="${APP:-jetpack}"
+export SIMULATOR_NAME="${SIMULATOR_NAME:-iPhone 16}"
+TEST_DIR="${TEST_DIR:-Tests/AgentTests/ui-tests}"
+SIMULATOR_LLM_PILOT_REPO_URL="${SIMULATOR_LLM_PILOT_REPO_URL:-https://github.com/Automattic/simulator-llm-pilot.git}"
+SIMULATOR_LLM_PILOT_SOURCE_PATH="${SIMULATOR_LLM_PILOT_SOURCE_PATH:-}"
+
+case "$APP" in
+  wordpress) APP_BUNDLE_ID="org.wordpress"; APP_DISPLAY_NAME="WordPress" ;;
+  jetpack)   APP_BUNDLE_ID="com.automattic.jetpack"; APP_DISPLAY_NAME="Jetpack" ;;
+  *) echo "Error: APP must be 'wordpress' or 'jetpack', got '$APP'" >&2; exit 1 ;;
+esac
+
+APP_INSTRUCTIONS_FILE="${REPO_ROOT}/Tests/AgentTests/app-instructions.md"
+
+# ── Artifact download (Buildkite only) ───────────────────────────────
+if [[ -n "${BUILDKITE:-}" ]]; then
+  echo "--- Downloading Build Artifacts"
+  download_artifact "build-products-${APP}.tar"
+  tar -xf "build-products-${APP}.tar"
+
+  echo "--- Setting up Gems"
+  install_gems
+fi
+
+# ── Install simulator-llm-pilot ──────────────────────────────────────
+echo "--- Installing simulator-llm-pilot"
+bash Scripts/ci/install-simulator-llm-pilot.sh
+echo "simulator-llm-pilot $(simulator-llm-pilot version)"
+
+# ── Resolve simulator and install app (Buildkite only) ───────────────
+echo "--- Setting up Simulator"
+
+UDID="$(ruby Scripts/ci/find-booted-simulator.rb "$SIMULATOR_NAME" 2>/dev/null || true)"
+if [[ -z "$UDID" ]]; then
+  echo "No booted simulator named '$SIMULATOR_NAME' found. Booting..."
+  xcrun simctl boot "$SIMULATOR_NAME" 2>/dev/null || true
+  UDID="$(ruby Scripts/ci/find-booted-simulator.rb "$SIMULATOR_NAME" 30 1 2>/dev/null || true)"
+fi
+
+if [[ -z "$UDID" ]]; then
+  echo "Error: could not find a booted simulator named '$SIMULATOR_NAME'" >&2
+  exit 1
+fi
+
+export SIMULATOR_UDID="$UDID"
+echo "Simulator UDID: $UDID"
+
+if [[ -n "${BUILDKITE:-}" ]]; then
+  APP_PATH=$(find DerivedData/Build/Products -name "${APP_DISPLAY_NAME}.app" -path "*Debug-iphonesimulator*" | head -1)
+  if [[ -z "$APP_PATH" ]]; then
+    echo "Error: ${APP_DISPLAY_NAME}.app not found in build products" >&2
+    exit 1
+  fi
+  echo "Installing $APP_PATH on simulator..."
+  xcrun simctl install "$UDID" "$APP_PATH"
+fi
+
+# ── Build WebDriverAgent (if not present) ────────────────────────────
+echo "--- Building WebDriverAgent"
+"$(dirname "$0")/build-wda.sh"
+
+# ── Run tests ────────────────────────────────────────────────────────
+echo "--- Running AI E2E Tests"
+
+TIMESTAMP="$(date +%Y-%m-%d-%H%M)"
+RESULTS_DIR="Tests/AgentTests/results/${TIMESTAMP}"
+
+EXIT_CODE=0
+simulator-llm-pilot run "$TEST_DIR" \
+  --app-bundle-id "$APP_BUNDLE_ID" \
+  --app-name "$APP_DISPLAY_NAME" \
+  --app-instructions-file "$APP_INSTRUCTIONS_FILE" \
+  --simulator-udid "$UDID" \
+  --results-dir "$RESULTS_DIR" \
+  || EXIT_CODE=$?
+
+# ── Report results ───────────────────────────────────────────────────
+echo "--- Results"
+RESULTS_FILE="${RESULTS_DIR}/results.md"
+if [[ -f "$RESULTS_FILE" ]]; then
+  cat "$RESULTS_FILE"
+else
+  echo "Warning: no results.md found at $RESULTS_FILE"
+fi
+
+exit "$EXIT_CODE"
diff --git a/.buildkite/pipeline.yml b/.buildkite/pipeline.yml
index 16ef55c325bf..0116632a3f22 100644
--- a/.buildkite/pipeline.yml
+++ b/.buildkite/pipeline.yml
@@ -138,6 +138,24 @@ steps:
         command: .buildkite/commands/lint-localized-strings-format.sh
         plugins: [$CI_TOOLKIT_PLUGIN]
 
+  #################
+  # AI E2E Tests (requires "Testing" label on PR)
+  #################
+  - label: "🤖 AI E2E Tests"
+    command: .buildkite/commands/run-ai-e2e-tests.sh
+    depends_on: "build_jetpack"
+    if: "build.pull_request.id != null"
+    soft_fail: true
+    timeout_in_minutes: 60
+    plugins: [$CI_TOOLKIT_PLUGIN]
+    env:
+      APP: jetpack
+    artifact_paths:
+      - "Tests/AgentTests/results/**/*"
+    notify:
+      - github_commit_status:
+          context: "AI E2E Tests"
+
   #################
   # Claude Build Analysis - dynamically uploaded so Build result conditions evaluate at runtime after the wait
   #################
diff --git a/.claude/skills/ai-test-runner/SKILL.md b/.claude/skills/ai-test-runner/SKILL.md
index c8f611c1dd9d..0828d9640920 100644
--- a/.claude/skills/ai-test-runner/SKILL.md
+++ b/.claude/skills/ai-test-runner/SKILL.md
@@ -96,7 +96,7 @@ Use the ios-sim-navigation skill for WDA interaction reference.
 
 ## Context
 
-- App Bundle ID: <BUNDLE_ID>
+- App Bundle ID: <APP_BUNDLE_ID>
 - WDA Session ID: <SESSION_ID>
 - Simulator UDID: <UDID>
 - Test file: <TEST_FILE_PATH> (absolute path)
@@ -117,7 +117,7 @@ Use the ios-sim-navigation skill for WDA interaction reference.
 2. **Relaunch the app** for a clean state:
 
    ```bash
-   xcrun simctl launch --terminate-running-process <UDID> <BUNDLE_ID> \
+   xcrun simctl launch --terminate-running-process <UDID> <APP_BUNDLE_ID> \
      -ui-test-site-url <SITE_URL> \
      -ui-test-site-user <USERNAME> \
      -ui-test-site-pass <APPLICATION_PASSWORD>
diff --git a/.claude/skills/ios-sim-navigation/SKILL.md b/.claude/skills/ios-sim-navigation/SKILL.md
index 0ec4ab7efab1..96cb6311aeb4 100644
--- a/.claude/skills/ios-sim-navigation/SKILL.md
+++ b/.claude/skills/ios-sim-navigation/SKILL.md
@@ -366,7 +366,7 @@ If actions consistently fail or the tree looks unexpected, the app may have cras
 xcrun simctl list devices booted
 
 # Re-launch the app
-xcrun simctl launch <UDID> <BUNDLE_ID>
+xcrun simctl launch <UDID> <APP_BUNDLE_ID>
 ```
 
 After re-launching, create a new WDA session before continuing.
diff --git a/Scripts/ci/find-booted-simulator.rb b/Scripts/ci/find-booted-simulator.rb
new file mode 100755
index 000000000000..67f33992366a
--- /dev/null
+++ b/Scripts/ci/find-booted-simulator.rb
@@ -0,0 +1,38 @@
+#!/usr/bin/env ruby
+# frozen_string_literal: true
+
+require 'json'
+require 'open3'
+
+requested_name = ARGV[0].to_s
+wait_seconds = ARGV[1].to_f
+poll_interval = ARGV[2].to_f
+poll_interval = 1.0 if poll_interval <= 0
+deadline = Process.clock_gettime(Process::CLOCK_MONOTONIC) + [wait_seconds, 0].max
+
+loop do
+  output, status = Open3.capture2('xcrun', 'simctl', 'list', 'devices', 'booted', '-j')
+  exit 1 unless status.success?
+
+  data = JSON.parse(output)
+  devices = data.fetch('devices', {}).each_value.flat_map do |list|
+    list.select { |device| device['state'] == 'Booted' }
+  end
+
+  device = if requested_name.empty?
+             devices.first
+           else
+             devices.find { |entry| entry['name'] == requested_name }
+           end
+
+  if device
+    print(device['udid'])
+    exit 0
+  end
+
+  break if wait_seconds <= 0 || Process.clock_gettime(Process::CLOCK_MONOTONIC) >= deadline
+
+  sleep poll_interval
+end
+
+exit 1
diff --git a/Scripts/ci/install-simulator-llm-pilot.sh b/Scripts/ci/install-simulator-llm-pilot.sh
new file mode 100644
index 000000000000..35f3b23bd2d7
--- /dev/null
+++ b/Scripts/ci/install-simulator-llm-pilot.sh
@@ -0,0 +1,48 @@
+#!/usr/bin/env bash
+set -euo pipefail
+
+SCRIPT_DIR="$(cd "$(dirname "$0")" && pwd)"
+REPO_ROOT="$(cd "$SCRIPT_DIR/../.." && pwd)"
+DEFAULT_LOCAL_GEM_PATH="$(cd "$REPO_ROOT/.." && pwd)/simulator-llm-pilot"
+
+SIMULATOR_LLM_PILOT_REPO_URL="${SIMULATOR_LLM_PILOT_REPO_URL:-https://github.com/Automattic/simulator-llm-pilot.git}"
+SIMULATOR_LLM_PILOT_SOURCE_PATH="${SIMULATOR_LLM_PILOT_SOURCE_PATH:-}"
+
+build_dir="$(mktemp -d)"
+trap 'rm -rf "$build_dir"' EXIT
+
+source_path="${SIMULATOR_LLM_PILOT_SOURCE_PATH}"
+if [[ -z "$source_path" && -f "${DEFAULT_LOCAL_GEM_PATH}/simulator-llm-pilot.gemspec" ]]; then
+  source_path="${DEFAULT_LOCAL_GEM_PATH}"
+fi
+
+if [[ -n "$source_path" ]]; then
+  echo "Using local simulator-llm-pilot source at ${source_path}"
+  if [[ -d "${source_path}/.git" ]]; then
+    source_revision="$(git -C "${source_path}" rev-parse HEAD)"
+    git -C "${source_path}" archive HEAD | tar -x -C "$build_dir"
+  else
+    source_revision="local-filesystem"
+    tar -cf - -C "${source_path}" . | tar -xf - -C "$build_dir"
+  fi
+else
+  echo "Cloning simulator-llm-pilot from ${SIMULATOR_LLM_PILOT_REPO_URL}"
+  git clone --depth 1 "${SIMULATOR_LLM_PILOT_REPO_URL}" "$build_dir"
+  source_revision="$(git -C "$build_dir" rev-parse HEAD)"
+fi
+
+pushd "$build_dir" >/dev/null
+gem build simulator-llm-pilot.gemspec >/dev/null
+shopt -s nullglob
+gem_files=(simulator-llm-pilot-*.gem)
+shopt -u nullglob
+
+if [[ ${#gem_files[@]} -ne 1 ]]; then
+  echo "Error: expected exactly one built simulator-llm-pilot gem, found ${#gem_files[@]}" >&2
+  exit 1
+fi
+
+gem install --no-document --force "./${gem_files[0]}"
+popd >/dev/null
+
+echo "Installed simulator-llm-pilot from ${source_revision}"
diff --git a/Tests/AgentTests/app-instructions.md b/Tests/AgentTests/app-instructions.md
new file mode 100644
index 000000000000..fc9bc168c3b3
--- /dev/null
+++ b/Tests/AgentTests/app-instructions.md
@@ -0,0 +1,13 @@
+## Login
+
+This app uses a self-hosted WordPress site login flow. The app password is
+passed via launch arguments — NEVER type a password manually.
+
+- NEVER tap "Continue with WordPress.com", NEVER enter WordPress.com
+  email/password, and NEVER request a login link.
+- Tap "Enter your existing site address", then enter the site host first
+  (without scheme, for example `example.com`). If the app rejects the
+  host-only form, try the full site URL once.
+- If you reach any WordPress.com email/password screen, back out and
+  return to the self-hosted flow.
+- If the app is already logged in (e.g., My Site tab visible), skip login.