On a couple of occasions I’ve created a document on my iPad (once a PDF, another time a jpeg) and it’s refused to sync to my iPhone. The file is listed but with a little cloud symbol. When I try and open the document it gives me a download option but when I select it nothing happens. I’ve tried restarting the app and the phone but nothing helps. There is no error message.
The solution seems to be go to the source device (my iPad) and duplicate the file. The duplicate will sync without problems. Then I can delete the original and rename the duplicate.
I have DTTG (premium) on an iPad and an iPhone, both have the “Download Files” option set to always. The sync store has an encryption password and is shared via dropbox. I can’t remember if I’ve been on WIFI or 3/4g when it happened.