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@Tim Macpherson Welcome to the Atlassian Community.
I am having difficulty reproducing. Are there any commonalities of the ones that are not displaying? (PDF Size, how they are attached, etc)
Can you provide a step by step of what you are doing?
My only experience of the issue is within table cells. I have never seen it occur outside a table. It does not always occur, but when it does for some reason, it remain the problem even if the PDF is deleted and re populated. It also occurs if the table cell or row is deleted and rebuilt. It’s like a page cache issue, except it persists even after clearing the cache and restarting the browser (safari).
When in edit mode, the PDF displays the thumbnail correctly.