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???
What are you trying to do?
Send to email only works when you do Send to email. What is this manual vs "automatic"?
Book conversions do not send to email, that would be disastrous -- every book anyone converted would automatically be emailed at random.
If you send to email and have only MOBI configured as a receiving format, calibre will prompt to auto-convert in order to send a matching format. (Same applies when sending to device.)
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