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I don't use this feature but here's what I can guess about it.
I would first suspect that something is blocking your outgoing email, it looks like Calbre uses a built in email server, perhaps your firewall or ISP is blocking outgoing email from it in attempts to block malware that sometimes send malicious stuff in and out on port 25 masquerading as email.
In Calibres setting try and change the email setting at the top (which looks like the destination email address) to your HOME email address and see if you get it there. If you DON'T get it then something is blocking it.
Optionally you may have to set up the email server that your Windows email program uses in the same options at the bottom in the SERVER options dialog.
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