diff --git a/anki/sync.py b/anki/sync.py
index 4803341ad..725cff79a 100644
--- a/anki/sync.py
+++ b/anki/sync.py
@@ -547,7 +547,7 @@ class MediaSyncer(object):
         while 1:
             runHook("mediaSync", "stream")
             zip = self.server.files()
-            if self.addFiles(zip=zip):
+            if self.addFiles(zip=zip) != "continue":
                 break
         # step 3: stream files to the server
         runHook("mediaSync", "client")
@@ -555,7 +555,7 @@ class MediaSyncer(object):
             runHook("mediaSync", "stream")
             zip = self.files()
             usn = self.server.addFiles(zip=zip)
-            if usn:
+            if usn != "continue":
                 # when server has run out of files, it returns bumped usn
                 break
         self.deck.media.setUsn(usn)
diff --git a/tests/test_sync.py b/tests/test_sync.py
index 2c52e83b0..4f9e03baa 100644
--- a/tests/test_sync.py
+++ b/tests/test_sync.py
@@ -358,8 +358,17 @@ def test_media():
     assert server.mediatest("count") == 0
     # we should be able to add it again
     time.sleep(1)
-    p = os.path.join(deck1.media.dir(), "foo.jpg")
     open(p, "wb").write("foo")
     client.sync()
     assert len(os.listdir(deck1.media.dir())) == 1
     assert server.mediatest("count") == 1
+    # if we modify it, it should get sent too. also we set the zip size very
+    # low here, so that we can test splitting into multiple zips
+    import anki.media; anki.media.SYNC_ZIP_SIZE = 1
+    time.sleep(1)
+    open(p, "wb").write("bar")
+    open(p+"2", "wb").write("baz")
+    assert len(os.listdir(deck1.media.dir())) == 2
+    client.sync()
+    assert len(os.listdir(deck1.media.dir())) == 2
+    assert server.mediatest("count") == 2