Hi @Angel_Hidalgo,
I believe I’ve identified the root cause. I was able to reproduce the behavior you described, and I found that when using tools like the Snipping Tool or Screenshot Tool, the system assigns the default filename “image.png” to each image. When two such images are added to a comment in Azure DevOps (ADO), the integration sends both with the same filename.
As a result, Jira Cloud displays the same image twice, even though two different images were originally added. This appears to be due to Jira interpreting both attachments as the same file because of the identical names.
However, if you save or rename the images with unique filenames before inserting them into the ADO comment, Jira Cloud correctly displays both images.
Recommended Workaround:
Try saving your screenshots with different names (e.g., image1.png, image2.png) before pasting them to the ADO comment. This should resolve the duplication issue you’re seeing in Jira Cloud.
Please let me know if this solves your issue