Yes, actually for both.
I've registered
name@gmail.com as a safe account to send from and when I send from there to the
name@free.kindle.com I'm able to receive it on my Kindle. I've also configured calibre to 'Send as'
name@gmail.com. So when I send to my gmail account from calibre, I get an email from 'me' to 'myself'. But, when I try to send to
name@free.kindle.com it doesn't go through. So far, the only guess I can make is that the Kindle servers are blocking calibre. Is there any other email address that I should add to the Kindle whitelist, other than my 'name@gmail.com'.