Outgoing email completely lost (Mail app with Gmail account) - Insanely awkward

This is gonna be hard to explain as I have no "evidence" but here's what happened for the 3rd time now in the last 2-3 months on Yosemite using a Gmail account from Mail app.
I write a mail (either reply or new one), send it and it get's completely lost. Can't find it anywhere neither from within the Mail app nor in Gmail's web interface. No error message, nothing. At first I thought I closed my laptop too soon after I hit the send button. I don't even know how to Google this issue, most of the similar issues and resolutions talk about SMTP and/or authentication errors, but again I don't have any error message.
In one instance the message was indeed not delivered, in another one (that just happened to me yesterday) the recipient received the message but I still can't find it.
Anyone ever experienced the same?
While this is very low amount of occurrence, it is still very very annoying and creates awkward situations in a business context. I always think people who say "I have sent the message, haven't you received it?" are lying because there's no way an email gets lost like this.. And now I'm the one for the third time that asks this the other party.
Anyone knows a way I could trace a message from some log file or anything? Any suggestions, insights are welcome.
Thanks
Dan

Troubleshooting Apple Mail
What does Mail/Window/Connection Doctor Show? If the server is red, select it and look at the Show Details box.
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<hr>
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