diff --git a/lib/zip/entry.rb b/lib/zip/entry.rb
index 8b17f3fc..df973c0d 100644
--- a/lib/zip/entry.rb
+++ b/lib/zip/entry.rb
@@ -572,6 +572,7 @@ def create_file(dest_path, _continue_on_exists_proc = proc { Zip.continue_on_exi
         raise ::Zip::DestinationFileExistsError,
               "Destination '#{dest_path}' already exists"
       end
+      ::FileUtils.mkdir_p(::File.dirname(dest_path))
       ::File.open(dest_path, 'wb') do |os|
         get_input_stream do |is|
           set_extra_attributes_on_path(dest_path)
diff --git a/test/file_extract_test.rb b/test/file_extract_test.rb
index 57833fcb..0a18e162 100644
--- a/test/file_extract_test.rb
+++ b/test/file_extract_test.rb
@@ -11,22 +11,11 @@ def setup
   end
 
   def test_extract
-    ::Zip::File.open(TEST_ZIP.zip_name) do |zf|
-      zf.extract(ENTRY_TO_EXTRACT, EXTRACTED_FILENAME)
-
-      assert(File.exist?(EXTRACTED_FILENAME))
-      AssertEntry.assert_contents(EXTRACTED_FILENAME,
-                                  zf.get_input_stream(ENTRY_TO_EXTRACT) { |is| is.read })
-
-      ::File.unlink(EXTRACTED_FILENAME)
-
-      entry = zf.get_entry(ENTRY_TO_EXTRACT)
-      entry.extract(EXTRACTED_FILENAME)
+    assert_extract(EXTRACTED_FILENAME)
+  end
 
-      assert(File.exist?(EXTRACTED_FILENAME))
-      AssertEntry.assert_contents(EXTRACTED_FILENAME,
-                                  entry.get_input_stream { |is| is.read })
-    end
+  def test_extract_nested_file
+    assert_extract('test/data/generated/a/b/c/extEntry')
   end
 
   def test_extract_exists
@@ -80,4 +69,25 @@ def test_extract_non_entry_2
     end
     assert(!File.exist?(outFile))
   end
+
+  private
+
+  def assert_extract(extracted_filename)
+    ::Zip::File.open(TEST_ZIP.zip_name) do |zf|
+      zf.extract(ENTRY_TO_EXTRACT, extracted_filename)
+
+      assert(File.exist?(extracted_filename))
+      AssertEntry.assert_contents(extracted_filename,
+                                  zf.get_input_stream(ENTRY_TO_EXTRACT) { |is| is.read })
+
+      ::File.unlink(extracted_filename)
+
+      entry = zf.get_entry(ENTRY_TO_EXTRACT)
+      entry.extract(extracted_filename)
+
+      assert(File.exist?(extracted_filename))
+      AssertEntry.assert_contents(extracted_filename,
+                                  entry.get_input_stream { |is| is.read })
+    end
+  end
 end