diff --git a/Library/Homebrew/test/cask/cmd/upgrade_spec.rb b/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
index 8f3ddfed67..2c0fff3d7b 100644
--- a/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/cmd/upgrade_spec.rb
@@ -71,9 +71,82 @@ describe Cask::Cmd::Upgrade, :cask do
         expect(local_transmission_path).to be_a_directory
         expect(local_transmission.versions).to include("2.60")
       end
+
+      it 'updates "auto_updates" and "latest" Casks when their tokens are provided in the command line' do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        auto_updates = Cask::CaskLoader.load("auto-updates")
+        auto_updates_path = Cask::Config.global.appdir.join("MyFancyApp.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+
+        described_class.run("local-caffeine", "auto-updates")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.3")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.61")
+      end
     end
 
     describe "with --greedy it checks additional Casks" do
+      it 'includes the Casks with "auto_updates true" or "version latest"' do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        auto_updates = Cask::CaskLoader.load("auto-updates")
+        auto_updates_path = Cask::Config.global.appdir.join("MyFancyApp.app")
+        local_transmission = Cask::CaskLoader.load("local-transmission")
+        local_transmission_path = Cask::Config.global.appdir.join("Transmission.app")
+        version_latest = Cask::CaskLoader.load("version-latest")
+        version_latest_path_1 = Cask::Config.global.appdir.join("Caffeine Mini.app")
+        version_latest_path_2 = Cask::Config.global.appdir.join("Caffeine Pro.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_1).to be_a_directory
+        expect(version_latest_path_2).to be_a_directory
+        expect(version_latest.versions).to include("latest")
+
+        described_class.run("--greedy")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.3")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.61")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.61")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_1).to be_a_directory
+        expect(version_latest_path_2).to be_a_directory
+        expect(version_latest.versions).to include("latest")
+      end
+
       it 'does not include the Casks with "auto_updates true" when the version did not change' do
         cask = Cask::CaskLoader.load("auto-updates")
         cask_path = cask.config.appdir.join("MyFancyApp.app")
@@ -97,6 +170,179 @@ describe Cask::Cmd::Upgrade, :cask do
     end
   end
 
+  context "dry run upgrade" do
+    let(:installed) {
+      [
+        "outdated/local-caffeine",
+        "outdated/local-transmission",
+        "outdated/auto-updates",
+        "outdated/version-latest",
+      ]
+    }
+
+    before do
+      installed.each { |cask| Cask::Cmd::Install.run(cask) }
+
+      allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
+    end
+
+    describe 'without --greedy it ignores the Casks with "version latest" or "auto_updates true"' do
+      it "would update all the installed Casks when no token is provided" do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        local_transmission = Cask::CaskLoader.load("local-transmission")
+        local_transmission_path = Cask::Config.global.appdir.join("Transmission.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        described_class.run("--dry-run")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+        expect(local_caffeine.versions).not_to include("1.2.3")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+        expect(local_transmission.versions).not_to include("2.61")
+      end
+
+      it "would update only the Casks specified in the command line" do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        local_transmission = Cask::CaskLoader.load("local-transmission")
+        local_transmission_path = Cask::Config.global.appdir.join("Transmission.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        described_class.run("--dry-run", "local-caffeine")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+        expect(local_caffeine.versions).not_to include("1.2.3")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+        expect(local_transmission.versions).not_to include("2.61")
+      end
+
+      it 'would update "auto_updates" and "latest" Casks when their tokens are provided in the command line' do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        auto_updates = Cask::CaskLoader.load("auto-updates")
+        auto_updates_path = Cask::Config.global.appdir.join("MyFancyApp.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+
+        described_class.run("--dry-run", "local-caffeine", "auto-updates")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+        expect(local_caffeine.versions).not_to include("1.2.3")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+        expect(auto_updates.versions).not_to include("2.61")
+      end
+    end
+
+    describe "with --greedy it checks additional Casks" do
+      it 'would include the Casks with "auto_updates true" or "version latest"' do
+        local_caffeine = Cask::CaskLoader.load("local-caffeine")
+        local_caffeine_path = Cask::Config.global.appdir.join("Caffeine.app")
+        auto_updates = Cask::CaskLoader.load("auto-updates")
+        auto_updates_path = Cask::Config.global.appdir.join("MyFancyApp.app")
+        local_transmission = Cask::CaskLoader.load("local-transmission")
+        local_transmission_path = Cask::Config.global.appdir.join("Transmission.app")
+        version_latest = Cask::CaskLoader.load("version-latest")
+        version_latest_path_1 = Cask::Config.global.appdir.join("Caffeine Mini.app")
+        version_latest_path_2 = Cask::Config.global.appdir.join("Caffeine Pro.app")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_1).to be_a_directory
+        expect(version_latest.versions).to include("latest")
+
+        described_class.run("--greedy", "--dry-run")
+
+        expect(local_caffeine).to be_installed
+        expect(local_caffeine_path).to be_a_directory
+        expect(local_caffeine.versions).to include("1.2.2")
+        expect(local_caffeine.versions).not_to include("1.2.3")
+
+        expect(auto_updates).to be_installed
+        expect(auto_updates_path).to be_a_directory
+        expect(auto_updates.versions).to include("2.57")
+        expect(auto_updates.versions).not_to include("2.61")
+
+        expect(local_transmission).to be_installed
+        expect(local_transmission_path).to be_a_directory
+        expect(local_transmission.versions).to include("2.60")
+        expect(local_transmission.versions).not_to include("2.61")
+
+        expect(version_latest).to be_installed
+        expect(version_latest_path_2).to be_a_directory
+      end
+
+      it 'does not include the Casks with "auto_updates true" when the version did not change' do
+        cask = Cask::CaskLoader.load("auto-updates")
+        cask_path = cask.config.appdir.join("MyFancyApp.app")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.57")
+
+        described_class.run("--dry-run", "auto-updates", "--greedy")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.57")
+        expect(cask.versions).not_to include("2.61")
+
+        described_class.run("--dry-run", "auto-updates", "--greedy")
+
+        expect(cask).to be_installed
+        expect(cask_path).to be_a_directory
+        expect(cask.versions).to include("2.57")
+        expect(cask.versions).not_to include("2.61")
+      end
+    end
+  end
+
   context "failed upgrade" do
     let(:installed) {
       [
diff --git a/Library/Homebrew/test/cask/pkg_spec.rb b/Library/Homebrew/test/cask/pkg_spec.rb
index fdcfe65fb6..486ab8f822 100644
--- a/Library/Homebrew/test/cask/pkg_spec.rb
+++ b/Library/Homebrew/test/cask/pkg_spec.rb
@@ -6,6 +6,34 @@ describe Cask::Pkg, :cask do
     let(:empty_response) { double(stdout: "", plist: { "volume" => "/", "install-location" => "", "paths" => {} }) }
     let(:pkg) { described_class.new("my.fake.pkg", fake_system_command) }
 
+    it "removes files and dirs referenced by the pkg" do
+      some_files = Array.new(3) { Pathname.new(Tempfile.new("plain_file").path) }
+      allow(pkg).to receive(:pkgutil_bom_files).and_return(some_files)
+
+      some_specials = Array.new(3) { Pathname.new(Tempfile.new("special_file").path) }
+      allow(pkg).to receive(:pkgutil_bom_specials).and_return(some_specials)
+
+      some_dirs = Array.new(3) { mktmpdir }
+      allow(pkg).to receive(:pkgutil_bom_dirs).and_return(some_dirs)
+
+      root_dir = Pathname.new(mktmpdir)
+      allow(pkg).to receive(:root).and_return(root_dir)
+
+      allow(pkg).to receive(:forget)
+
+      pkg.uninstall
+
+      some_files.each do |file|
+        expect(file).not_to exist
+      end
+
+      some_dirs.each do |dir|
+        expect(dir).not_to exist
+      end
+
+      expect(root_dir).not_to exist
+    end
+
     context "pkgutil" do
       it "forgets the pkg" do
         allow(fake_system_command).to receive(:run!).with(
diff --git a/Library/Homebrew/test/spec_helper.rb b/Library/Homebrew/test/spec_helper.rb
index 28c020bfc1..7ac1062bdd 100644
--- a/Library/Homebrew/test/spec_helper.rb
+++ b/Library/Homebrew/test/spec_helper.rb
@@ -78,6 +78,17 @@ RSpec.configure do |config|
     c.max_formatted_output_length = 200
   end
 
+  # Use rspec-retry in CI.
+  if ENV["CI"]
+    config.verbose_retry = true
+    config.display_try_failure_messages = true
+    config.default_retry_count = 2
+
+    config.around(:each, :needs_network) do |example|
+      example.run_with_retry retry: 3, retry_wait: 3
+    end
+  end
+
   # Never truncate output objects.
   RSpec::Support::ObjectFormatter.default_instance.max_formatted_output_length = nil
 
@@ -124,10 +135,6 @@ RSpec.configure do |config|
     skip "Requires network connection." unless ENV["HOMEBREW_TEST_ONLINE"]
   end
 
-  config.around(:each, :needs_network) do |example|
-    example.run_with_retry retry: 3, retry_wait: 1
-  end
-
   config.before(:each, :needs_svn) do
     skip "subversion not installed." unless quiet_system "#{HOMEBREW_SHIMS_PATH}/scm/svn", "--version"