diff --git a/lib/rubygems/package.rb b/lib/rubygems/package.rb
index 89aa84a1c733..d36b6dfb5e9a 100644
--- a/lib/rubygems/package.rb
+++ b/lib/rubygems/package.rb
@@ -453,6 +453,11 @@ def extract_tar_gz(io, destination_dir, pattern = "*") # :nodoc:
           directories << mkdir
         end
 
+        real_mkdir = File.realpath(mkdir)
+        unless real_mkdir == destination_dir || normalize_path(real_mkdir).start_with?(normalize_path(destination_dir + "/"))
+          raise Gem::Package::PathError.new(real_mkdir, destination_dir)
+        end
+
         if entry.file?
           File.open(destination, "wb") do |out|
             copy_stream(tar.io, out, entry.size)
diff --git a/test/rubygems/test_gem_package.rb b/test/rubygems/test_gem_package.rb
index 43d4a07bd496..0014c2073727 100644
--- a/test/rubygems/test_gem_package.rb
+++ b/test/rubygems/test_gem_package.rb
@@ -615,6 +615,32 @@ def test_extract_tar_gz_symlink_directory
                  File.read(extracted)
   end
 
+  def test_extract_tar_gz_rejects_preexisting_symlink_escape
+    omit "Symlinks not supported or not enabled" unless symlink_supported?
+
+    package = Gem::Package.new @gem
+
+    tgz_io = util_tar_gz do |tar|
+      tar.add_file "lib/owned.txt", 0o644 do |io|
+        io.write "poc-content"
+      end
+    end
+
+    escape_dir = File.join(@tempdir, "escape")
+    FileUtils.mkdir_p escape_dir
+
+    FileUtils.rm_rf File.join(@destination, "lib")
+    File.symlink escape_dir, File.join(@destination, "lib")
+
+    escaped = File.join(escape_dir, "owned.txt")
+
+    assert_raise Gem::Package::PathError do
+      package.extract_tar_gz tgz_io, @destination
+    end
+
+    refute File.exist?(escaped), "must not write outside extraction root via symlink"
+  end
+
   def test_extract_symlink_into_symlink_dir
     omit "Symlinks not supported or not enabled" unless symlink_supported?
     package = Gem::Package.new @gem