diff --git a/lib/capistrano/transfer.rb b/lib/capistrano/transfer.rb
index c1b75e88..b9c8f693 100644
--- a/lib/capistrano/transfer.rb
+++ b/lib/capistrano/transfer.rb
@@ -203,6 +203,8 @@ module Capistrano
       end
 
       def handle_error(error)
+        raise error if error.message.include?('expected a file to upload')
+
         transfer = session_map[error.session]
         transfer[:error] = error
         transfer[:failed] = true
diff --git a/test/transfer_test.rb b/test/transfer_test.rb
index f98c44b2..9fbeab81 100644
--- a/test/transfer_test.rb
+++ b/test/transfer_test.rb
@@ -133,6 +133,14 @@ class TransferTest < Test::Unit::TestCase
     transfer.process!
   end
 
+  def test_uploading_a_non_existing_file_should_raise_an_understandable_error
+    s = session('app1')
+    error = Capistrano::Processable::SessionAssociation.on(ArgumentError.new('expected a file to upload'), s)
+    transfer = Capistrano::Transfer.new(:up, "from", "to", [], :via => :scp)
+    transfer.expects(:process_iteration).raises(error)
+    assert_raise(ArgumentError, 'expected a file to upload') { transfer.process! }
+  end
+
   private
 
     class ExceptionWithSession < ::Exception