diff --git a/Library/Homebrew/cask/lib/hbc/installer.rb b/Library/Homebrew/cask/lib/hbc/installer.rb
index cf71639efa..88b77c62c7 100644
--- a/Library/Homebrew/cask/lib/hbc/installer.rb
+++ b/Library/Homebrew/cask/lib/hbc/installer.rb
@@ -426,7 +426,7 @@ module Hbc
     end
 
     def purge_versioned_files(upgrade: false)
-      ohai "Purging files for version #{@cask.version} of Cask #{@cask}" unless upgrade?
+      odebug "Purging files for version #{@cask.version} of Cask #{@cask}" unless upgrade?
 
       # versioned staged distribution
       gain_permissions_remove(@cask.staged_path) if !@cask.staged_path.nil? && @cask.staged_path.exist?
@@ -441,10 +441,10 @@ module Hbc
         end
       end
       @cask.metadata_versioned_path.rmdir_if_possible
-      @cask.metadata_master_container_path.rmdir_if_possible unless upgrade
+      @cask.metadata_master_container_path.rmdir_if_possible unless upgrade?
 
       # toplevel staged distribution
-      @cask.caskroom_path.rmdir_if_possible unless upgrade
+      @cask.caskroom_path.rmdir_if_possible unless upgrade?
     end
 
     def purge_caskroom_path
diff --git a/Library/Homebrew/test/cask/cli/upgrade_spec.rb b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
index 532541ba7a..38e57fc5e0 100644
--- a/Library/Homebrew/test/cask/cli/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/cli/upgrade_spec.rb
@@ -1,24 +1,31 @@
 require_relative "shared_examples/invalid_option"
 
 describe Hbc::CLI::Upgrade, :cask do
-  let(:installed) do
-    [
-      Hbc::CaskLoader.load(cask_path("outdated/local-caffeine")),
-      Hbc::CaskLoader.load(cask_path("outdated/local-transmission")),
-      Hbc::CaskLoader.load(cask_path("outdated/auto-updates")),
-    ]
-  end
-
   it_behaves_like "a command that handles invalid options"
 
   before(:example) do
-    installed.each { |cask| InstallHelper.install_with_caskfile(cask) }
+    installed =
+      [
+        "outdated/local-caffeine",
+        "outdated/local-transmission",
+        "outdated/auto-updates",
+      ]
+
+    installed.each { |cask| Hbc::CLI::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 "updates all the installed Casks when no token is provided" do
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
+      expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.2")
+
+      expect(Hbc::CaskLoader.load("local-transmission")).to be_installed
+      expect(Hbc.appdir.join("Transmission.app")).to be_a_directory
+      expect(Hbc::CaskLoader.load("local-transmission").versions).to include("2.60")
+
       described_class.run
 
       expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
@@ -31,47 +38,89 @@ describe Hbc::CLI::Upgrade, :cask do
     end
 
     it "updates only the Casks specified in the command line" do
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.2")
+
+      expect(Hbc::CaskLoader.load("local-transmission")).to be_installed
+      expect(Hbc.appdir.join("Transmission.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-transmission").versions).to include("2.60")
 
       described_class.run("local-caffeine")
 
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.3")
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to_not include("1.2.2")
+
+      expect(Hbc::CaskLoader.load("local-transmission")).to be_installed
+      expect(Hbc.appdir.join("Transmission.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-transmission").versions).to include("2.60")
     end
 
     it 'ignores "auto_updates" and "latest" Casks even when their tokens are provided in the command line' do
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.2")
+
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.57")
 
-      described_class.run("local-caffeine", "auto-updates", "version-latest-string")
+      described_class.run("local-caffeine", "auto-updates")
 
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.3")
+
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.57")
     end
   end
 
   describe "with --greedy it checks additional Casks" do
     it 'includes the Casks with "auto_updates true" or "version latest" with --greedy' do
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.57")
+
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.2")
+
       expect(Hbc::CaskLoader.load("local-transmission").versions).to include("2.60")
 
       described_class.run("--greedy")
 
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.61")
+
+      expect(Hbc::CaskLoader.load("local-caffeine")).to be_installed
+      expect(Hbc.appdir.join("Caffeine.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-caffeine").versions).to include("1.2.3")
+
+      expect(Hbc::CaskLoader.load("local-transmission")).to be_installed
+      expect(Hbc.appdir.join("Transmission.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("local-transmission").versions).to include("2.61")
     end
 
     it 'does not include the Casks with "auto_updates true" when the version did not change' do
-      cask = Hbc::CaskLoader.load(cask_path("auto-updates"))
-      InstallHelper.install_with_caskfile(cask)
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
+      expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.57")
+
+      described_class.run("auto-updates", "--greedy")
+
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.61")
 
       described_class.run("auto-updates", "--greedy")
 
+      expect(Hbc::CaskLoader.load("auto-updates")).to be_installed
+      expect(Hbc.appdir.join("MyFancyApp.app")).to be_a_directory
       expect(Hbc::CaskLoader.load("auto-updates").versions).to include("2.61")
     end
   end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
index 1cada2561c..4f61455bb1 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/auto-updates.rb
@@ -1,11 +1,11 @@
 cask 'auto-updates' do
   version '2.61'
-  sha256 'e44ffa103fbf83f55c8d0b1bea309a43b2880798dae8620b1ee8da5e1095ec68'
+  sha256 '5633c3a0f2e572cbf021507dec78c50998b398c343232bdfc7e26221d0a5db4d'
 
-  url "file://#{TEST_FIXTURE_DIR}/cask/transmission-2.61.dmg"
-  homepage 'http://example.com/auto-updates'
+  url "file://#{TEST_FIXTURE_DIR}/cask/MyFancyApp.zip"
+  homepage 'http://example.com/MyFancyApp'
 
   auto_updates true
 
-  app 'Transmission.app'
+  app 'MyFancyApp/MyFancyApp.app'
 end
diff --git a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
index e202f5a163..5844a0762c 100644
--- a/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
+++ b/Library/Homebrew/test/support/fixtures/cask/Casks/outdated/auto-updates.rb
@@ -1,11 +1,11 @@
 cask 'auto-updates' do
   version '2.57'
-  sha256 'e44ffa103fbf83f55c8d0b1bea309a43b2880798dae8620b1ee8da5e1095ec68'
+  sha256 '5633c3a0f2e572cbf021507dec78c50998b398c343232bdfc7e26221d0a5db4d'
 
-  url "file://#{TEST_FIXTURE_DIR}/cask/transmission-2.61.dmg"
-  homepage 'http://example.com/auto-updates'
+  url "file://#{TEST_FIXTURE_DIR}/cask/MyFancyApp.zip"
+  homepage 'http://example.com/MyFancyApp'
 
   auto_updates true
 
-  app 'Transmission.app'
+  app 'MyFancyApp/MyFancyApp.app'
 end