2 files changed, 25 insertions, 0 deletions
diff --git a/Library/Homebrew/cask/lib/hbc/pkg.rb b/Library/Homebrew/cask/lib/hbc/pkg.rb
index 2fb634f24..497a7b6dd 100644
--- a/Library/Homebrew/cask/lib/hbc/pkg.rb
+++ b/Library/Homebrew/cask/lib/hbc/pkg.rb
@@ -26,6 +26,7 @@ module Hbc
       _deepest_path_first(pkgutil_bom_dirs).each do |dir|
         next unless dir.exist? && !MacOS.undeletable?(dir)
         _with_full_permissions(dir) do
+          _delete_broken_file_dir(dir) && next
           _clean_broken_symlinks(dir)
           _clean_ds_store(dir)
           _rmdir(dir)
@@ -97,6 +98,13 @@ module Hbc
       end
     end
 
+    # Some pkgs (microsoft office for one) leave files (generally nibs) but
+    # report them as directories.  We remove these as files instead.
+    def _delete_broken_file_dir(path)
+      return unless path.file? && !path.symlink?
+      @command.run!("/bin/rm", args: ["-f", "--", path], sudo: true)
+    end
+
     # Some pkgs leave broken symlinks hanging around; we clean them out before
     # attempting to rmdir to prevent extra cruft from lying around after
     # uninstall
diff --git a/Library/Homebrew/cask/test/cask/pkg_test.rb b/Library/Homebrew/cask/test/cask/pkg_test.rb
index 85a42356e..b99d49ddd 100644
--- a/Library/Homebrew/cask/test/cask/pkg_test.rb
+++ b/Library/Homebrew/cask/test/cask/pkg_test.rb
@@ -68,6 +68,23 @@ describe Hbc::Pkg do
       fake_dir.must_be :exist?
     end
 
+    it "chokes on directories that are really files" do
+      pkg = Hbc::Pkg.new("my.fake.pkg", Hbc::NeverSudoSystemCommand)
+
+      fake_dir  = Pathname(Dir.mktmpdir)
+      fake_file = fake_dir.join("ima_file").tap { |path| FileUtils.touch(path) }
+
+      pkg.stubs(:pkgutil_bom_specials).returns([])
+      pkg.stubs(:pkgutil_bom_files).returns([])
+      pkg.stubs(:pkgutil_bom_dirs).returns([fake_file, fake_dir])
+      pkg.stubs(:forget)
+
+      pkg.uninstall
+
+      fake_file.wont_be :exist?
+      fake_dir.wont_be :exist?
+    end
+
     it "snags permissions on ornery dirs, but returns them afterwords" do
       pkg = Hbc::Pkg.new("my.fake.pkg", Hbc::NeverSudoSystemCommand)