If you are sending an email with a file attachment such as documents, videos, PDFs, or pictures.
Follow these methods and check whichever works for you: Method 1: Check file size. We are listing the possible solutions to fix emails stuck in the Outbox of Gmail. But there are times when I want/need to keep the Date header the same (yes, it can be forged) and the time stamp of the cryptographic signature the same as the original send date and time. Fix emails stuck in Outbox queued and not sending in Gmail. Yes, I am aware of the Message » Send Again menu option. Recently, I serendipitously stumbled upon the solution: Drag the offending messages to the Outbox folder in the folders pane (which you'll only have if you tried to send messages while offline). Still, every once in a while, I'd still have messages that defy even that treatment. It used to be that sending another message via the same server would prod it into sending both messages, but somewhere along the way, Apple fixed that "feature." Usually quitting and restarting Mail.app (a lame solution to my mind) would cause it to retry. Synchronize Accounts does nothing (and never has). But every once in a while, a message gets stuck Mail.app flatly refuses to try to redeliver it. I also tend to send messages while disconnected, so they stay in my Outbox until I reconnect. I tend to use my PowerBook while disconnected. Maybe that's because the solution was obvious to everyone but myself. But that doesn't describe the situation I've encountered. The closest thing I'd ever found was the Workaround for a stuck outbound Mail message hint. Every few months for the last several years, this particular problem annoyed me enough that I searched this site and the web in general for a possible solution.
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