Mail is too temperamental – what else is there?
I have an iMac running Mavericks. Using the Apple Mail app to send/receive from my Gmail account is a real problem. For some reason a mail can get replicated many times and dumped into Trash. Sometimes a message is sent, then appears in the Outbox as if it hasn’t been sent. So I am looking for a replacement mail system that is reliable, simple to use, and works well with Gmail – but I don’t want to lose my existing mail. Jeff I think it’s worth persevering with Apple Mail. When a message appears in Outbox, it’s not ‘as if’ it hasn’t been sent – it really hasn’t. The Outbox folder only appears when a message can’t be sent, and it auto-deletes itself when the message successfully sends.
The real question then, is why can’t you send? Since you’re using an iMac, you are presumably at home, with a trustworthy connection, and you don’t mention changing any email server settings recently. But they could be corrupt, so a good first step is to trash com.apple.mail.plist and com.apple.mail-shared.plist from ~/Library/ Preferences. Delete the files that begin with ‘Envelope Index’ from ~/Library/Mail/V2/ MailData. Restart Mail and follow the prompts to rebuild the index. If you still want another app, try Inky (free, inky.com).