Separately convert before sending, though if you try to send an epub it will offer to convert it to what ever format is top of the list.
Make sure the FW is last version and the Fonts have a Publisher Option. If there is no Publisher option then you can only convert to old mobi or dual mobi. If there is a Publisher option (at least all Kindle firmware from 3.4.3) then convert to azw3 and make it top of the list of formats in Calibre device driver (may only be visible when Kindle connected).
I'd guess you can have 4.1.4
Quote:
Kindle (4th and 5th Generation)
Latest version: 4.1.4
Download Software Update
Note: If your device is on a version older than 4.1.3, please visit Previous Software Updates for Kindle E-Reader for instructions.
Kindle Touch (4th Generation)
5.3.7.3
Download Software Update
Note: If your device is on an older version than 5.3.2, 5.3.2.1, 5.3.7, 5.3.7.1 or 5.3.7.2, please Previous Software Updates for Kindle E-Reader for instructions.
Kindle Keyboard (3rd Generation)
3.4.3
Your serial number starts with B008 download this file.
Your serial number starts with B006 download this file.
Your serial number starts with B00A download this file.
Note: If your device is on a version older than 3.4.2, please visit Previous Software Updates for Kindle E-Reader for instructions.
https://www.amazon.com/gp/help/custo...MQC26VQQMM8XSW
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Your Kindle might support the Kindle Collections plug-in.
You might want to edit the AZW3 css and make the left & right margins -40px which is a good reason to convert before sending as the Kindle default minimum margins are huge!