Question about (and possible help with) reuploading books, please

[Bookprincess]

Hello

I have a very important (to me) question and would appreciate some help.

If a book (that's already ON my Kindle paperwhite, via the 'upload to device' option, so it's not on the cloud, and it has notes!) If I reupload this same file, via email (through Calibre), will the new file have the notes?
(Like, if I reupload a same file via 'upload to device', it just replaces the old one and saves all the notes, does it do that too when I send to email as well?)

If it doesn't replace the old file but adds another new file, is there a way to save\transfer\attach the old notes, to the new file??
(I need to do that to many many books, and even more notes...) so manually won't work...So pleaseeeeee tell me the notes are transferred no matter how I reupload the same file

(I hope it makes sense...)
Please help, and thank you very much

[jhowell]

The emailed book will be treated as a new book, separate and distinct from any existing copy already on your device. Notes, annotations and reading progress will not transfer over.

The new copy of the book will have annotations synced from Amazon's servers and won't have any to start with. There is a file on your device for each book that has it's annotations, but as far as I know copying it over from the old book to the new one won't work since that data will eventually be overwritten by the master copy from your account.

[Bookprincess]

I see. Thank you so much for your detailed reply! You've helped me a lot. (I mean, I'm stuck now, but it was very important for me to know, and I thank you.)

Follow up question- when one day I get a new Kindle (which I assume I will have to, at some point), would I be able to transfer my books WITH the notes there?
Not by email, just uploaded to device like I do now, just to a new device. Like if I will copy this file that has the annotation there, would it have my notes? (No Amazon cloud or sync involved)

Thanks in advance.

[Deskisamess]

Books purchased from Amazon will have your notes and highlights backed up on their "cloud" if you have that option enabled on your Kindle.

[jhowell]

Originally Posted by Bookprincess

Follow up question- when one day I get a new Kindle (which I assume I will have to, at some point), would I be able to transfer my books WITH the notes there?
Not by email, just uploaded to device like I do now, just to a new device. Like if I will copy this file that has the annotation there, would it have my notes? (No Amazon cloud or sync involved)

I do not know how well it would work and I do not know of any easy or automatic way to do that. Perhaps someone with experience in transferring sideloaded books between Kindles will respond with more information.

As it stands you are at risk of losing all of your notes if you break or lose your Kindle.