exalating attachments (pasted images) on azuredevops result in transferred into same-name files on the receiving JIRA side,

this means you need to save copies & rename manually before being able to differentiate between the diff files. 

This should be avoided. Appreciate a workaround for this / a solution to deal with this.

Unfortunately, AzureDevOps stores these attachments inline, without visible filenames, so I assume that the filename given is determined by the outgoing issue filter  processing. 

Thanks,

Ben