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There is no way to directly send books to the Kindle app (or any app other than iBooks) on Apple devices.
The option you have for getting books into the Kindle app are:
- Send the books via email and your Amazon Kindle account. This works so you may need to post information about the error you are getting to get it to work.
- Save the books to disk from Calibre and then Use the iTunes facility to load books into an app and select the Kindle app. However you say you have this working and are unhappy with it.
- Use the Calibre Content Server (or an equivalent) with a web browser and use the facility in the browser for loading books into apps. You say you start the Content Server and nothing happens? What are you expecting to see? Nothing will be visible at the PC. You need to use the browser at the iOS end.
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