Q: Apple Mail sending sometimes stuck, restart loses mail

Sometimes I send email and it does not send, it states "Senidng mail" on the bottom left status bar, and the mail is stuck in the outbox. Its not a size issue, mail is small. It happens on my Macbook at home, and on my iMac in work.

I have the quit mail, then re-open, and once re-opened the mail sends.

But today I noticed an email that I "sent" was not in my Sent items. I have no idea if it was sent or not now. I have to rewrite it and send again, or ask the recipient if they just got it. Both unprofessional!

Anyone else have this issue? I'm going to have to switch to another app if I cant fix it.

Thanks