See the support request# #408720 for the integration error with for a work item with more than one attachment with same name. Resolution provided by Aha! support is to rename the image.png files differently so that DevOps accepts them. Can Aha! Implement automatically naming images with a number appended in the end. So that we do not really have to change the names every time. Thank you.
Image.png
Image(1).png
Image(2).png