1) I Compose a messege in Gmail App 2) The message sends 3) The message is received by the recipient 4) The message is not in the Sent folder (Sent Label) 5) The message(s) are in the Outbox Label and states Sending... In red letters. For some reason, these messages are NOT leaving the Outbox and NOT going into the SENT folder. This is only happening on emails using the following filter: This is a quick email shortcut whereby I update Xpenser - Mobile Expense Tracking and Management entries. I setup a filter such that it does not save the message into my Sent items and to go to trash. It works fine on the web. In fact, there's no Outbox label on the web interface. The message is in the trash as it should be. I think since this is a unique issue based on the unique folder I have to avoid the Sent Items and move it to trash. I have to manually delete these items, it's a pain. I think I may just simple remove this filter, and from time to time, do a search for firstname.lastname@example.org and delete all these messages. This appears to be a bug in the Gmail App. Again, all other sending is working fine and they're going directly into Sent items label. It's only the ones where I have the unique filter above set on. .