diff --git a/Library/Homebrew/test/cask/upgrade_spec.rb b/Library/Homebrew/test/cask/upgrade_spec.rb
index 374c289634..35df63722f 100644
--- a/Library/Homebrew/test/cask/upgrade_spec.rb
+++ b/Library/Homebrew/test/cask/upgrade_spec.rb
@@ -25,7 +25,6 @@ describe Cask::Upgrade, :cask do
     installed.each do |cask|
       Cask::Installer.new(Cask::CaskLoader.load(cask_path(cask))).install
     end
-    FileUtils.rm_rf CoreCaskTap.instance.cask_dir/"outdated"
 
     allow_any_instance_of(described_class).to receive(:verbose?).and_return(true)
   end
diff --git a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
index 67f9078c95..798cf246c6 100644
--- a/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
+++ b/Library/Homebrew/test/support/helper/spec/shared_context/homebrew_cask.rb
@@ -39,9 +39,16 @@ RSpec.shared_context "Homebrew Cask", :needs_macos do # rubocop:disable RSpec/Co
       Cask::Config::DEFAULT_DIRS_PATHNAMES.each_value(&:mkpath)
 
       CoreCaskTap.instance.tap do |tap|
-        tap.cask_dir.mkpath
-        (TEST_FIXTURE_DIR/"cask/Casks").children.each do |casks_path|
-          FileUtils.ln_sf casks_path, tap.cask_dir
+        fixture_cask_dir = TEST_FIXTURE_DIR/"cask/Casks"
+        fixture_cask_dir.glob("**/*.rb").each do |fixture_cask_path|
+          relative_cask_path = fixture_cask_path.relative_path_from(fixture_cask_dir)
+
+          # These are only used manually in tests since they
+          # would otherwise conflict with other casks.
+          next if relative_cask_path.dirname.basename.to_s == "outdated"
+
+          cask_dir = (tap.cask_dir/relative_cask_path.dirname).tap(&:mkpath)
+          FileUtils.ln_sf fixture_cask_path, cask_dir
         end
       end