Hi @Billy Branca welcome to the community. I don't have your exact workflow, but in general I am seeing my files in my instance. I also checked the Atlassian Status Page and didn't see anything specific about that issue.
Does the issue happen using the same browser (ie, have you tried at least both Edge & Chrome).
I do see some issues about images failing to load under different circumstances. I used this search criteria on Atlassian's Jira Site:
project = "Confluence Cloud" and text ~ image and text ~ load and status != closed
I'd suggest taking a look at that if your workflow could be related to any of those, and certainly vote for and watch if any of those apply.
Hope that helps.
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