diff --git a/lib/google/apis/core/upload.rb b/lib/google/apis/core/upload.rb
index af4007433..723dbc94f 100644
--- a/lib/google/apis/core/upload.rb
+++ b/lib/google/apis/core/upload.rb
@@ -178,7 +178,6 @@ module Google
         def process_response(status, header, body)
           @offset = Integer(header[BYTES_RECEIVED_HEADER]) if header.key?(BYTES_RECEIVED_HEADER)
           @upload_url = header[UPLOAD_URL_HEADER] if header.key?(UPLOAD_URL_HEADER)
-
           upload_status = header[UPLOAD_STATUS_HEADER]
           logger.debug { sprintf('Upload status %s', upload_status) }
           if upload_status == STATUS_ACTIVE
@@ -254,12 +253,16 @@ module Google
         # @raise [Google::Apis::ClientError] The request is invalid and should not be retried without modification
         # @raise [Google::Apis::AuthorizationError] Authorization is required
         def execute_once(client, &block)
-          if @state == :start
+          case @state
+          when :start
             response = send_start_command(client)
-          else
+            result = process_response(response.status_code, response.header, response.body)
+          when :active
             response = send_query_command(client)
+            result = process_response(response.status_code, response.header, response.body)
+          when :cancelled, :final
+            error(@last_error, rethrow: true, &block)
           end
-          result = process_response(response.status_code, response.header, response.body)
           if @state == :active
             response = send_upload_command(client)
             result = process_response(response.status_code, response.header, response.body)
@@ -267,6 +270,10 @@ module Google
 
           success(result, &block) if @state == :final
         rescue => e
+          # Some APIs like Youtube generate non-retriable 401 errors and mark
+          # the upload as finalized. Save the error just in case we get
+          # retried.
+          @last_error = e
           error(e, rethrow: true, &block)
         end
       end
diff --git a/spec/google/apis/core/upload_spec.rb b/spec/google/apis/core/upload_spec.rb
index b6265a8c3..e18c60119 100644
--- a/spec/google/apis/core/upload_spec.rb
+++ b/spec/google/apis/core/upload_spec.rb
@@ -49,7 +49,7 @@ RSpec.describe Google::Apis::Core::UploadIO do
       end
 
       it 'should setup length of the stream' do
-        upload_io = Google::Apis::Core::UploadIO.from_file(file) 
+        upload_io = Google::Apis::Core::UploadIO.from_file(file)
         expect(upload_io.length).to eq File.size(file)
       end
 
@@ -60,9 +60,9 @@ RSpec.describe Google::Apis::Core::UploadIO do
 
     context 'with i/o stream' do
       let(:io) { StringIO.new 'Hello google' }
-      
+
       it 'should setup default content-type' do
-        upload_io = Google::Apis::Core::UploadIO.from_io(io)  
+        upload_io = Google::Apis::Core::UploadIO.from_io(io)
         expect(upload_io.content_type).to eql Google::Apis::Core::UploadIO::OCTET_STREAM_CONTENT_TYPE
       end
 
@@ -72,7 +72,7 @@ RSpec.describe Google::Apis::Core::UploadIO do
       end
 
       it 'should setup length of the stream' do
-        upload_io = Google::Apis::Core::UploadIO.from_io(io) 
+        upload_io = Google::Apis::Core::UploadIO.from_io(io)
         expect(upload_io.length).to eq 'Hello google'.length
       end
     end
@@ -244,6 +244,17 @@ RSpec.describe Google::Apis::Core::ResumableUploadCommand do
     end
   end
 
+  context 'with non-retriable authorization error on start' do
+    before(:example) do
+      stub_request(:post, 'https://www.googleapis.com/zoo/animals')
+        .to_return(status: [401, 'unauthorized'], headers: { 'X-Goog-Upload-Status' => 'final' }, body: %(unauthorized))
+    end
+
+    it 'should propagate the original error' do
+      expect { command.execute(client) }.to raise_error Google::Apis::AuthorizationError
+    end
+  end
+
   context 'with interruption' do
     before(:example) do
       stub_request(:post, 'https://www.googleapis.com/zoo/animals')