diff --git a/Library/Homebrew/cask/artifact/abstract_uninstall.rb b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
index 0cfdcad7ba..2242b7961a 100644
--- a/Library/Homebrew/cask/artifact/abstract_uninstall.rb
+++ b/Library/Homebrew/cask/artifact/abstract_uninstall.rb
@@ -468,9 +468,7 @@ module Cask
         trashed = trashed.split(":")
         untrashable = untrashable.split(":")
 
-        return trashed, untrashable if untrashable.empty?
-
-        untrashable.delete_if do |path|
+        trashed_with_permissions, untrashable = untrashable.partition do |path|
           Utils.gain_permissions(path, ["-R"], SystemCommand) do
             system_command! HOMEBREW_LIBRARY_PATH/"cask/utils/trash.swift",
                             args:         [path],
@@ -482,6 +480,10 @@ module Cask
           false
         end
 
+        trashed += trashed_with_permissions
+
+        return trashed, untrashable if untrashable.empty?
+
         opoo "The following files could not be trashed, please do so manually:"
         $stderr.puts untrashable