The Jira Mixin extension for Adobe allows users of Photoshop, Illustrator, and InDesign to attach assets to a Jira issue without leaving their Adobe product.
With a document open in your Adobe software, bring up the Jira Mixin extension. Then you can click on Connect [filename] to Jira. Select the project and then the issue that you would like to attach to. A Connect to Jira will appear and clicking on it will bring you to the issue view.
From the issue view, you can comment as well as attach the last saved version of your open file.