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I ran into this problem, trying to print a very tall PNG, over multiple pages.
Whatever I tried, It didn't work. Preview and others try to squeeze it on a single page.
By coincidence I found a solution: by using either Google Chrome or Safari ...
Open the image in your browser (right click - open with worked for me, but drag and drop will probably work as well).
Next print the page and increase the scale % (in Chrome up to 200%).
You'll see that the PNG is now spread over multiple pages. 😊
