Some item attachments not syncing to web

I'm having a problem where some of my item attachments (book pdfs) are not syncing to my web account, and thus not syncing across my devices. I went through the Knowledge Base and checked all the sync troubleshooting steps. I'm looking in the right places, I'm not seeing a sync error, my library is set to sync, etc. I did the further troubleshooting and generated this report and ID: D655087156

In this log, I started by removing the attached file from the item that isn't syncing, re-adding the file, and then hitting sync. It still isn't syncing to my web library.
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