diff --git a/bundler/lib/bundler/source/git/git_proxy.rb b/bundler/lib/bundler/source/git/git_proxy.rb
index 5dc1c8de32d7..7ac47044b30c 100644
--- a/bundler/lib/bundler/source/git/git_proxy.rb
+++ b/bundler/lib/bundler/source/git/git_proxy.rb
@@ -118,7 +118,7 @@ def copy_to(destination, submodules = false)
               git_retry %(clone --no-checkout --quiet "#{path}" "#{destination}")
               File.chmod(((File.stat(destination).mode | 0o777) & ~File.umask), destination)
             rescue Errno::EEXIST => e
-              file_path = e.message[%r{.*?(/.*)}, 1]
+              file_path = e.message[%r{.*?((?:[a-zA-Z]:)?/.*)}, 1]
               raise GitError, "Bundler could not install a gem because it needs to " \
                 "create a directory, but a file exists - #{file_path}. Please delete " \
                 "this file and try again."
diff --git a/bundler/spec/install/gemfile/git_spec.rb b/bundler/spec/install/gemfile/git_spec.rb
index a70fb18c45c6..3c6a4aa5905b 100644
--- a/bundler/spec/install/gemfile/git_spec.rb
+++ b/bundler/spec/install/gemfile/git_spec.rb
@@ -933,8 +933,6 @@
   end
 
   it "prints a friendly error if a file blocks the git repo" do
-    skip "drive letter is not detected correctly in error message" if Gem.win_platform?
-
     build_git "foo"
 
     FileUtils.mkdir_p(default_bundle_path)