diff --git a/src/calibre/devices/interface.py b/src/calibre/devices/interface.py
index 2d82bf4563..da8a2cb978 100644
--- a/src/calibre/devices/interface.py
+++ b/src/calibre/devices/interface.py
@@ -289,7 +289,10 @@ class DevicePlugin(Plugin):
         word "card" if C{on_card} is not None otherwise it must contain the word "memory".
         :files: A list of paths and/or file-like objects. If they are paths and
         the paths point to temporary files, they may have an additional
-        attribute, original_file_path pointing to the originals.
+        attribute, original_file_path pointing to the originals. They may have
+        another optional attribute, deleted_after_upload which if True means
+        that the file pointed to by original_file_path will be deleted after
+        being uploaded to the device.
         :names: A list of file names that the books should have
         once uploaded to the device. len(names) == len(files)
         :return: A list of 3-element tuples. The list is meant to be passed
diff --git a/src/calibre/gui2/device.py b/src/calibre/gui2/device.py
index 0e18929d81..1445b0f36e 100644
--- a/src/calibre/gui2/device.py
+++ b/src/calibre/gui2/device.py
@@ -854,6 +854,7 @@ class DeviceMixin(object):
 
     def sync_news(self, send_ids=None, do_auto_convert=True):
         if self.device_connected:
+            del_on_upload = config['delete_news_from_library_on_upload']
             settings = self.device_manager.device.settings()
             ids = list(dynamic.get('news_to_be_synced', set([]))) if send_ids is None else send_ids
             ids = [id for id in ids if self.library_view.model().db.has_id(id)]
@@ -883,6 +884,8 @@ class DeviceMixin(object):
                             'the device?'), det_msg=autos):
                         self.auto_convert_news(auto, format)
             files = [f for f in files if f is not None]
+            for f in files:
+                f.deleted_after_upload = del_on_upload
             if not files:
                 dynamic.set('news_to_be_synced', set([]))
                 return
@@ -900,8 +903,7 @@ class DeviceMixin(object):
                         'rb').read())
             dynamic.set('news_to_be_synced', set([]))
             if config['upload_news_to_device'] and files:
-                remove = ids if \
-                    config['delete_news_from_library_on_upload'] else []
+                remove = ids if del_on_upload else []
                 space = { self.location_view.model().free[0] : None,
                     self.location_view.model().free[1] : 'carda',
                     self.location_view.model().free[2] : 'cardb' }
diff --git a/src/calibre/gui2/library/models.py b/src/calibre/gui2/library/models.py
index abd80aaa8f..71f41eab45 100644
--- a/src/calibre/gui2/library/models.py
+++ b/src/calibre/gui2/library/models.py
@@ -39,6 +39,7 @@ class FormatPath(unicode):
     def __new__(cls, path, orig_file_path):
         ans = unicode.__new__(cls, path)
         ans.orig_file_path = orig_file_path
+        ans.deleted_after_upload = False
         return ans
 
 class BooksModel(QAbstractTableModel): # {{{