AFAIK the difference between bold font and regular or italic is only whether a message has been 'read'. What you're doing by shuffling them between Outbox and Drafts is repeatedly attempting to let the server pick up the message. When you move the message to drafts, you're cancelling the 'send' order. When you move it back into the outbox you're telling it to send it again. It's exactly the same as opening it and hitting the 'send' button.