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Originally Posted by KDA1
Is there a way to set it up without using Gmail?
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You can try, but gmail is what the creator of calibre recommends. After much trial and error I managed to set mine up with a hotmail account when I had no luck with gmail.
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Do the emailed books get sent to the kindle.com address? That is...does Amazon "see" the books one sends using the Calibre mail thing?
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The books go through their server, so yeah, they can "see" them. If you have Personal Document Archiving enabled they'll be storing a copy on their cloud for you as well.
The @kindle.com address is sort of a clone of whatever email address you used to set up your Amazon account and its destination is your Kindle. If you use the @kindle.com address, then Amazon will send the document to your device using Whispernet (and charge you $0.15-0.99/MB depending where you are). If you use the @free.kindle.com address, then the document will download to your device the next time you turn on wifi. You'll also get an email from Amazon to the email address you used for your account with a link for the document that you can download to your computer and load via cable, in case you aren't able to connect to wifi.
If you are planning to email lots of books to your Kindle, I'd recommend manually using your regular email account and attaching 15-25 books at a time instead of using calibre. Calibre has a 5 minute delay per send built in, so that it doesn't get blocked by spam filters, which makes it very slow for sending more than a few books at a time. You also have the option of loading the books onto your device with a cable, of course.