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One issue with this though is that you are relying on Calibre to do a conversion.
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You are relying on Amazon to do the conversions.
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My original post is dealing with the fact that Amazon state RTF is supported (whether natively or converted as it is sent) and yet the metadata is ignored, at least on files I tried so far. The fact that a third party application can retain the metadata as it creates mobi files ready for the Kindle is not really the issue - you are feeding the Kindle a mobi not an RTF so the result has no bearing on the Kindle's handling of RTF but rather on its handling of Calibre's mobi output.
Could you clarify your comment confirming that the Kindle cannot read RTF and requires a mobi conversion?
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If you hook your Kindle up to your computer and directly transfer an RTF file via USB into the documents folder it will not be visible, because RTF is not a supported file format.
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It is possible to pass an RTF directly to the Kindle account without converting into any other form. The Kindle sees it and shows it fine (minus metadata). It may well be that upon arrival we have a mobi internally, but the actual file sent to the Kindle is RTF not mobi, there is no Calibre involvement, no conversions. And the Kindle is fine with that (apart from the metadata of course).
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You are not passing it directly to the kindle, you are passing it through the Amazon conversion service. So your kindle never sees an RTF file.
The only possible way to get your files to be viewed on the Kindle is via conversion, whether that be done via Amazon's conversion service or via Calibre. No matter what you are not viewing an RTF on the Kindle. Yes, Amazon's conversion service accepts RTF but the Kindle itself does not.