diff --git a/notebook/services/contents/filemanager.py b/notebook/services/contents/filemanager.py
index aa89e0ab1d..f8ad4c9a00 100644
--- a/notebook/services/contents/filemanager.py
+++ b/notebook/services/contents/filemanager.py
@@ -14,6 +14,7 @@
 import mimetypes
 import nbformat
 
+from send2trash import send2trash
 from tornado import web
 
 from .filecheckpoints import FileCheckpoints
@@ -149,6 +150,11 @@ def _validate_root_dir(self, proposal):
     def _checkpoints_class_default(self):
         return FileCheckpoints
 
+    delete_to_trash = Bool(True, config=True,
+        help="""If True (default), deleting files will send them to the
+        platform's trash/recycle bin, where they can be recovered. If False,
+        deleting files really deletes them.""")
+
     @default('files_handler_class')
     def _files_handler_class_default(self):
         return AuthenticatedFileHandler
@@ -493,6 +499,14 @@ def delete_file(self, path):
         elif not os.path.isfile(os_path):
             raise web.HTTPError(404, u'File does not exist: %s' % os_path)
 
+        if self.delete_to_trash:
+            self.log.debug("Sending %s to trash", os_path)
+            # Looking at the code in send2trash, I don't think the errors it
+            # raises let us distinguish permission errors from other errors in
+            # code. So for now, just let them all get logged as server errors.
+            send2trash(os_path)
+            return
+
         if os.path.isdir(os_path):
             self.log.debug("Removing directory %s", os_path)
             with self.perm_to_403():
diff --git a/setup.py b/setup.py
index 1bab382833..7add23d2bb 100755
--- a/setup.py
+++ b/setup.py
@@ -152,6 +152,7 @@
     'nbformat',
     'nbconvert',
     'ipykernel', # bless IPython kernel for now
+    'Send2Trash',
 ]
 extras_require = {
     ':sys_platform != "win32"': ['terminado>=0.3.3'],