Decouple launchd from package paths

CHANGELOG.md

@@ -3,12 +3,24 @@
 All notable changes are documented here. AI Optimizer follows semantic
 versioning.
 
+## 0.1.6 - 2026-08-22
+
+- Keep the configured AI Optimizer executable out of the launchd plist
+  entirely; a versioned product-owned launcher embeds its absolute path with
+  shell-safe quoting.
+- Make launcher identity stable across Homebrew keg target changes and refuse
+  drifted or symlinked launcher files.
+- Add live-upgrade regression coverage using a Homebrew revision change that
+  removes the prior Cellar directory.
+
 ## 0.1.5 - 2026-08-22
 
 - Replace the short-lived `/usr/bin/env` launch item with a stable,
   product-owned maintenance launcher under Application Support.
 - Keep the exact AI Optimizer executable out of launchd's program arguments so
-  Homebrew keg replacement does not unregister an opted-in schedule.
+  it is not the registered launch program. This was superseded by v0.1.6 after
+  live evidence showed an executable path in plist environment state was still
+  associated with keg replacement.
 - Refuse symlinked launcher targets and install the launcher atomically with
   owner-only permissions.
 

README.md

@@ -33,7 +33,7 @@ skills, repositories, or launchd unless you explicitly add `--schedule`.
 Example:
 
 ```text
-AI Optimizer 0.1.5
+AI Optimizer 0.1.6
 
 [PASS] system.macos - macOS is supported
 [PASS] tools.claude.present - Claude Code is available
@@ -77,9 +77,10 @@ later in the morning records `skipped_outside_window` and performs no scan.
 Configuration, receipts, and scheduler logs are stored with owner-only
 permissions.
 The launch agent uses an owner-only, product-owned maintenance launcher under
-Application Support. The launcher reads AI Optimizer's absolute executable
-path from its launchd environment, keeping package upgrades from silently
-unregistering an already opted-in schedule.
+Application Support. Its versioned filename is stable for the configured
+executable path, and the Homebrew or direct-install path does not appear in the
+launchd plist. Package upgrades therefore leave an already opted-in schedule
+registered.
 
 AI Optimizer owns only:
 
@@ -120,7 +121,7 @@ The direct path verifies the installer before it runs, then the installer
 verifies the release archive before changing live paths:
 
 ```sh
-VERSION=0.1.5
+VERSION=0.1.6
 curl -fLO "https://github.com/nyldn/ai-optimizer/releases/download/v$VERSION/install.sh"
 curl -fLO "https://github.com/nyldn/ai-optimizer/releases/download/v$VERSION/install.sh.sha256"
 shasum -a 256 -c install.sh.sha256

VERSION

@@ -1 +1 @@
-0.1.5
+0.1.6

docs/privacy.md

@@ -1,6 +1,6 @@
 # Privacy
 
-AI Optimizer 0.1.5 has no telemetry and sends no diagnostic data anywhere.
+AI Optimizer 0.1.6 has no telemetry and sends no diagnostic data anywhere.
 
 ## Read
 
@@ -32,7 +32,8 @@ write or remove only AI Optimizer-owned files and the documented launchd label.
 Scheduled maintenance writes one local run receipt after the execution-time
 evening guard. Configuration, receipts, and scheduler logs use owner-only
 permissions. Its fixed maintenance launcher is also owner-only and uses only
-the exact executable path written by the explicit `schedule` command.
+the shell-quoted absolute executable path written by the explicit `schedule`
+command. That path does not appear in the launchd plist.
 
 AI Optimizer refuses to claim a nonempty Application Support directory unless
 its state manifest already proves product ownership.

lib/ai_optimizer/scheduler.rb

@@ -1,17 +1,14 @@
 # frozen_string_literal: true
 
 require "cgi"
+require "digest"
 require "fileutils"
 
 module AIOptimizer
   class Scheduler
     LABEL = "io.github.nyldn.ai-optimizer.daily"
     LOG_FILES = %w[daily.out.log daily.err.log].freeze
-    WRAPPER_NAME = "ai-optimizer-maintenance"
-    WRAPPER_CONTENT = <<~'SH'.freeze
-      #!/bin/sh
-      exec "$AI_OPTIMIZER_EXECUTABLE" run-maintenance
-    SH
+    WRAPPER_NAME = "ai-optimizer-maintenance-v1"
 
     attr_reader :launch_agents_dir, :data_dir, :executable, :uid, :runner
 
@@ -104,8 +101,10 @@ def ensure_owned_paths
       return unless File.file?(plist_path)
 
       content = File.binread(plist_path, 64_000)
+      versioned_wrapper = %r{/#{Regexp.escape(WRAPPER_NAME)}-[0-9a-f]{12}</string>}
       command_owned = content.include?("<string>run-maintenance</string>") ||
-                      content.include?("/#{WRAPPER_NAME}</string>")
+                      content.include?("/ai-optimizer-maintenance</string>") ||
+                      content.match?(versioned_wrapper)
       owned = content.include?("<string>#{LABEL}</string>") && command_owned
       raise OwnershipError, "existing launch agent is not provably owned by AI Optimizer" unless owned
     end
@@ -143,7 +142,16 @@ def secure_log_files
     end
 
     def maintenance_wrapper_path
-      File.join(data_dir, "bin", WRAPPER_NAME)
+      digest = Digest::SHA256.hexdigest(executable)[0, 12]
+      File.join(data_dir, "bin", "#{WRAPPER_NAME}-#{digest}")
+    end
+
+    def maintenance_wrapper_content
+      "#!/bin/sh\nexec #{shell_quote(executable)} run-maintenance\n"
+    end
+
+    def shell_quote(value)
+      "'#{value.gsub("'", %q('"'"'))}'"
     end
 
     def write_maintenance_wrapper
@@ -153,9 +161,18 @@ def write_maintenance_wrapper
 
       FileUtils.mkdir_p(bin_dir, mode: 0o700)
       File.chmod(0o700, bin_dir)
-      temporary = File.join(bin_dir, ".#{WRAPPER_NAME}.#{Process.pid}.tmp")
+      if File.exist?(maintenance_wrapper_path)
+        existing = File.file?(maintenance_wrapper_path) && File.binread(maintenance_wrapper_path)
+        expected = maintenance_wrapper_content.dup.force_encoding(Encoding::BINARY)
+        raise OwnershipError, "existing maintenance launcher does not match AI Optimizer" unless existing == expected
+
+        File.chmod(0o700, maintenance_wrapper_path)
+        return
+      end
+
+      temporary = File.join(bin_dir, ".#{File.basename(maintenance_wrapper_path)}.#{Process.pid}.tmp")
       File.open(temporary, File::WRONLY | File::CREAT | File::EXCL, 0o700) do |file|
-        file.write(WRAPPER_CONTENT)
+        file.write(maintenance_wrapper_content)
         file.flush
         file.fsync
       end
@@ -205,8 +222,6 @@ def plist(hour, minute)
             <string>/opt/homebrew/bin:/usr/local/bin:/usr/bin:/bin:/usr/sbin:/sbin</string>
             <key>AI_OPTIMIZER_DATA_DIR</key>
             <string>#{escape(data_dir)}</string>
-            <key>AI_OPTIMIZER_EXECUTABLE</key>
-            <string>#{escape(executable)}</string>
           </dict>
           <key>StandardOutPath</key>
           <string>#{escape(File.join(log_dir, "daily.out.log"))}</string>

test/scheduler_test.rb

@@ -1,5 +1,6 @@
 # frozen_string_literal: true
 
+require "digest"
 require_relative "test_helper"
 
 class SchedulerTest < Minitest::Test
@@ -25,16 +26,15 @@ def test_default_evening_schedule_round_trip_is_exact_and_idempotent
       assert_includes plist, "io.github.nyldn.ai-optimizer.daily"
       assert_includes plist, "<integer>21</integer>"
       refute_includes plist, "com.chris"
-      wrapper_path = File.join(dir, "data", "bin", "ai-optimizer-maintenance")
+      wrapper_digest = Digest::SHA256.hexdigest("/usr/local/bin/ai-optimizer")[0, 12]
+      wrapper_path = File.join(dir, "data", "bin", "ai-optimizer-maintenance-v1-#{wrapper_digest}")
       expected_program = %r{<key>ProgramArguments</key>\s*<array>\s*<string>#{Regexp.escape(wrapper_path)}</string>\s*</array>}
       assert_match expected_program, plist
-      assert_match %r{<key>AI_OPTIMIZER_EXECUTABLE</key>\s*<string>/usr/local/bin/ai-optimizer</string>}, plist
-      assert_equal "#!/bin/sh\nexec \"$AI_OPTIMIZER_EXECUTABLE\" run-maintenance\n", File.read(wrapper_path)
+      refute_includes plist, "AI_OPTIMIZER_EXECUTABLE"
+      refute_includes plist, "/usr/local/bin/ai-optimizer"
+      assert_equal "#!/bin/sh\nexec '/usr/local/bin/ai-optimizer' run-maintenance\n", File.read(wrapper_path)
       assert_equal 0o700, File.stat(File.dirname(wrapper_path)).mode & 0o777
       assert_equal 0o700, File.stat(wrapper_path).mode & 0o777
-      stdout, stderr, status = Open3.capture3({ "AI_OPTIMIZER_EXECUTABLE" => "/usr/bin/printf" }, wrapper_path)
-      assert status.success?, stderr
-      assert_equal "run-maintenance", stdout
       scheduler.schedule(hour: 21, minute: 0)
       assert File.file?(scheduler.plist_path)
       %w[daily.out.log daily.err.log].each do |name|
@@ -101,10 +101,13 @@ def test_schedule_refuses_a_symlinked_maintenance_launcher
       FileUtils.mkdir_p(bin_dir)
       external = File.join(dir, "external-launcher")
       File.write(external, "must remain unchanged\n")
-      File.symlink(external, File.join(bin_dir, "ai-optimizer-maintenance"))
+      executable = "/usr/local/bin/ai-optimizer"
+      wrapper_digest = Digest::SHA256.hexdigest(executable)[0, 12]
+      wrapper_path = File.join(bin_dir, "ai-optimizer-maintenance-v1-#{wrapper_digest}")
+      File.symlink(external, wrapper_path)
       scheduler = AIOptimizer::Scheduler.new(
         launch_agents_dir: File.join(dir, "agents"), data_dir: data_dir,
-        executable: "/usr/local/bin/ai-optimizer", uid: 501,
+        executable: executable, uid: 501,
         runner: TestSupport::FakeCommandRunner.new
       )
 
@@ -113,6 +116,56 @@ def test_schedule_refuses_a_symlinked_maintenance_launcher
     end
   end
 
+  def test_maintenance_launcher_executes_the_exact_configured_path
+    in_tmpdir do |dir|
+      agents = File.join(dir, "agents")
+      executable_dir = File.join(dir, "tool's bin-José")
+      FileUtils.mkdir_p(executable_dir)
+      executable = File.join(executable_dir, "ai optimizer")
+      File.write(executable, "#!/bin/sh\nprintf '%s' \"$1\"\n")
+      File.chmod(0o700, executable)
+      plist_path = File.join(agents, "io.github.nyldn.ai-optimizer.daily.plist")
+      runner = TestSupport::FakeCommandRunner.new(
+        "/bin/launchctl print gui/501/io.github.nyldn.ai-optimizer.daily" => { status: 1, stdout: "", stderr: "not found" },
+        "/usr/bin/plutil -lint #{File.join(agents, ".io.github.nyldn.ai-optimizer.daily.plist.tmp")}" => { status: 0, stdout: "OK", stderr: "" },
+        "/bin/launchctl bootstrap gui/501 #{plist_path}" => { status: 0, stdout: "", stderr: "" }
+      )
+      scheduler = AIOptimizer::Scheduler.new(
+        launch_agents_dir: agents, data_dir: File.join(dir, "data"),
+        executable: executable, uid: 501, runner: runner
+      )
+
+      scheduler.schedule(hour: 21, minute: 0)
+      scheduler.schedule(hour: 21, minute: 0)
+
+      wrapper_digest = Digest::SHA256.hexdigest(executable)[0, 12]
+      wrapper_path = File.join(dir, "data", "bin", "ai-optimizer-maintenance-v1-#{wrapper_digest}")
+      stdout, stderr, status = Open3.capture3(wrapper_path)
+      assert status.success?, stderr
+      assert_equal "run-maintenance", stdout
+    end
+  end
+
+  def test_schedule_refuses_a_drifted_maintenance_launcher
+    in_tmpdir do |dir|
+      data_dir = File.join(dir, "data")
+      bin_dir = File.join(data_dir, "bin")
+      FileUtils.mkdir_p(bin_dir)
+      executable = "/usr/local/bin/ai-optimizer"
+      wrapper_digest = Digest::SHA256.hexdigest(executable)[0, 12]
+      wrapper_path = File.join(bin_dir, "ai-optimizer-maintenance-v1-#{wrapper_digest}")
+      File.write(wrapper_path, "unowned content\n")
+      scheduler = AIOptimizer::Scheduler.new(
+        launch_agents_dir: File.join(dir, "agents"), data_dir: data_dir,
+        executable: executable, uid: 501,
+        runner: TestSupport::FakeCommandRunner.new
+      )
+
+      assert_raises(AIOptimizer::OwnershipError) { scheduler.schedule(hour: 21, minute: 0) }
+      assert_equal "unowned content\n", File.read(wrapper_path)
+    end
+  end
+
   def test_rejects_outside_window_without_explicit_override
     in_tmpdir do |dir|
       scheduler = AIOptimizer::Scheduler.new(