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What are known work-arounds to use calibre to send documents through its e-mail service?

https://the-digital-reader.com/2020/06/05/when-did-amazon-start-demanding-that-you-verify-your-ebooks-before-they-get-converted-and-sent-to-your-kindle/

https://www.reddit.com/r/kindle/comments/dl58gz/amazon_emailing_me_to_verify_every_book_i_sent_to/

The five-filters Firefox add-on suggested changing the "sent from" e-mail:

Send from address

To avoid spam, Amazon requires all documents sent to your Send-to-Kindle address to come from an approved e-mail address. You can add 'kindle@fivefilters.org' as an approved address using the following steps:

Load the 'Content and Devices' page on Amazon (link for UK users)
Click the 'Preferences' tab at the top of the page
Click 'Personal Document Settings'
Scroll down to the 'Approved Personal Document E-Mail List' section
Click 'Add a new approved e-mail address'
Enter 'kindle@fivefilters.org' and click 'Add Address'

and this seems to work. Is there some similar setting which can be made with calibre?

(Yes, there's a security exploit so that a document might have an attached virus, but, at a certain point, it's also caveat emptor. I certainly wouldn't hold Amazon responsible for me sending myself a virus.)

I haven't tried this, but I don't think it's so much using their kindle@fivefilters.com address so much as that the sent-from and reply-to probably need to match. Perhaps there's a similar e-mail address which can be used with calibre?

(Obviously, as calibre doesn't have my e-mail password it's not literally sending from my e-mail account.)

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