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Are there any risks of information loss when converting formats?

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Is there any risk associated with converting a book from say epub -> AZW3, or AZW3 -> EPUB?

And specifically in the case of epubs, are there formats which are closer in file structure, therefore safer or 'better' to convert to?

Context: I'm a calibre-web user and I am finding that the 'send to ereader' button does not appear for some of my epubs until I convert them from epub to another format and then back to epub.

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