Have you inserted your sidebar manually or do you merge with/replace a sidebar registered by your theme?
Replaced.
I’m also having an issue with the sidebar only appearing in certain pages even though I set added “All pages” to the conditions group. Our homepage is not displaying the sidebar, whitest other pages do.
If you want the sidebar to be displayed on your home page, create a new condition group and add the static page “Front Page” to it.
For your original question: Do you only want the content aware sidebar to be resized, or should it also be the sidebar it replaces?