Hi @MikeFowler,
I just wanted to check in — are you still experiencing this issue?
We’re currently discussing a very similar case in the following community thread:
DevOps–Jira Attachments Discussion
Please take a look at my latest comment there. The problem seems to be related to how images are added in Azure DevOps (ADO) — specifically when using tools like Snipping Tool, which assign the default name image.png to each screenshot. This can cause issues when syncing to Jira Cloud, where images with the same filename may not be handled as unique files.
Let me know if the explanation in the thread aligns with what you’re experiencing