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This one is still reproducible in 7.3.Our users create content not in Liferay. They do it in a word processor for a number of reasons, collaboration, the fact that work won't be lost and other things like spellcheck. Anyways when they copy paste it into Alloy or CK the images that are within the content pasted will never make it into the documents and media portlet.

7.3 GA3 - Blog portlet can't upload embedded images from created post
https://issues.liferay.com/browse/LPS-115764


At some point this did work, at some point it stopped working. We still have an issue too where pasting from word that has "Smart Quotes" enabled, words like it's and you're are having the apostrophe stripped , it could be anti-sammy but it had never been an issue until a fix pack update.