: Shipping self-published books directly from Amazon to bookstores: bad idea? I have a book published by Kindle Direct Publishing. Most of my sales are to bookstores and up until now I have

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You may be in breach of contract if you sell your books anywhere but Amazon.
I'm not having much luck finding definitive contract information about this but according to one source an exclusivity agreement with Amazon's KDP Select program will forbid you from selling in other marketplaces. This restriction only applies to the "Select" program.
It also appears that Amazon has gone from it being difficult for bookstores to order direct (via Ingrams) to basically impossible.

From: "http://Amazon.com" mailto:kdp-customersupport1@amazon.com
Subject: Your Amazon KDP Inquiry
Date: January 24, 2019 at 10:06:53 PM CST
"From your email I understand you want to know how can your vendors
order wholesale copies of your book …
Unfortunately in KDP does not offer CreateSpace Direct as a
distribution option so that copies of your book can be ordered at
wholesale price. They will have to now place order for your books from
Amazon at the price list on Amazon."

So your options are to have the bookstore place their own wholesale order through a distributor like Ingrams or for you to do what you suggest, buy author copies and send them to the bookstore.
It's unclear if your books will even be in the distributor catalog, but it's worth checking. This is the best option. Completely above board and what most bookstores prefer.
For you to buy and ship books means double shipping fees (if you aren't local to the store) and it's unclear if it's allowed by your contract. If you ship the books directly to the store you avoid double shipping fees but it may not be allowed.
I don't understand why you're asking about the Amazon-branded boxes. If the bookstore wants copies of your book in this way, they won't care what boxes they come in. If you're sending them on spec, well, it's a waste of your money.

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