I got an email from work to get a copy of a document to them. I use Scanner Pro to scan documents to PDF, so I figure okay, no problem. I use Mailbox, not default mail. So I fire up Mailbox, open the email, hit reply, write my message, tap the paper clip and... oh. That's for Dropbox links. Okay, what about the camera icon? No go. That's just pictures from the camera roll. All righty, let's go into Scanner Pro. Open up the PDF there and hit the envelope... and it says I need to set up mail accounts. I disabled sync through the stock mail app in order to use Mailbox (avoiding double notifications). So that meant I had to go back into settings, re-enable sync, and THEN I can send a new mail with the attachment, not a reply. Oh wait! I can COPY the attachment from my message and paste it into a reply. So let's do the steps, in order, for someone who uses a third party email app: Go into settings, re-enable sync for Mail Go to the app with the PDF, hit share, choose email Copy attachment from message. Re-open mail, this time going into your conversation thread. Paste copied attachment into reply. Send. Go BACK into settings, disable sync from Mail. That is hilariously unintuitive when all I want to do is respond to an email with a document. Is there a faster method I don't know about?