diff --git a/lib/asset_sync/storage.rb b/lib/asset_sync/storage.rb
index 28232e9..fdac4ab 100644
--- a/lib/asset_sync/storage.rb
+++ b/lib/asset_sync/storage.rb
@@ -264,7 +264,8 @@ def upload_file(f)
       if config.compression
         compressed_name = "#{path}/#{f}.#{config.compression}"
 
-        if File.extname(f) == config.compression
+        # `File.extname` returns value with `.` prefix, `config.compression` contains value without `.`
+        if File.extname(f)[1..-1] == config.compression
           # Don't bother uploading compressed assets if we are in compression mode
           # as we will overwrite file.css with file.css.gz if it exists.
           log "Ignoring: #{f}"
diff --git a/spec/unit/storage_spec.rb b/spec/unit/storage_spec.rb
index cc7d1d3..1d68768 100644
--- a/spec/unit/storage_spec.rb
+++ b/spec/unit/storage_spec.rb
@@ -393,6 +393,46 @@ def check_file(file)
       end
       storage.upload_file('assets/some_longer_path/local_image2.jpg')
     end
+
+    context 'config.gzip_compression is enabled' do
+      context 'when the file is a css file' do
+        it 'should upload the file' do
+          @config.gzip_compression = true
+
+          storage = AssetSync::Storage.new(@config)
+          allow(storage).to receive(:get_local_files).and_return(@local_files)
+          allow(storage).to receive(:get_remote_files).and_return(@remote_files)
+          # Pretend they all exist
+          allow(File).to receive(:open).and_return(file_like_object)
+          bucket = double
+          files = double
+          allow(storage).to receive(:bucket).and_return(bucket)
+          allow(bucket).to receive(:files).and_return(files)
+
+          expect(files).to receive(:create).with({ body: file_like_object, content_type: "text/css", key: "assets/local.css", public: true }).once
+          storage.upload_file('assets/local.css')
+        end
+      end
+
+      context 'when the file is a gz file' do
+        it 'should not upload the file' do
+          @config.gzip_compression = true
+
+          storage = AssetSync::Storage.new(@config)
+          allow(storage).to receive(:get_local_files).and_return(@local_files)
+          allow(storage).to receive(:get_remote_files).and_return(@remote_files)
+          # Pretend they all exist
+          allow(File).to receive(:open).and_return(file_like_object)
+          bucket = double
+          files = double
+          allow(storage).to receive(:bucket).and_return(bucket)
+          allow(bucket).to receive(:files).and_return(files)
+
+          expect(files).to_not receive(:create)
+          storage.upload_file('assets/local.css.gz')
+        end
+      end
+    end
   end
 
   describe '#delete_extra_remote_files' do