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Hi, coffeeGrounds
Since attachments sync fine and only printouts fail, the problem seems to be in the web app's step that converts your file into page images. That doesn't explain why the standalone apps work, but it does give you a few ways around it.
Here are some suggestions you can try:
Insert the printout in the standalone app, then open the same page in OneNote for the web and resize the printout images there. A printout is basically a stack of images, so once it syncs you can drag each one to the size you want in the web version. If it doesn't show up right in the web view, it is recommended to copy the printout from the app and paste it onto the page in the web version.
Skip the printout feature and use Insert > Picture instead. Save each page of your file as a PNG or JPG first. On a Mac, you can export PDF pages as images from Preview. Pictures don't go through the conversion step that's failing, so they should load right away in the web version.
If your files are Word or PowerPoint docs, export them to PDF first and insert the PDF as the printout. Also try a short file name with no special characters.
Delete the stuck page with the red X before you try again, since a broken printout can keep failing to sync. Copy anything you need from it to a new page first.