Go to Preferences->Sharing books by email. If the only field that is filled in is the "Send email from:" field and all of the fields below "calibre can
optionally use a server to send email" are empty. Then it's not fully configured to use gmail's smtp server. It's just
pretending it's sending from your gmail address and Amazon's servers aren't buying it. Click the big "Use GMail" button on the left and fill in your gmail account info and login/pwd. Then try the test.
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and set it up to automatically email the gmail address in preferences. Anything else that should be done?
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You don't want it to email your gmail address you want it to email your kindle's email address... through gmail.