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In Jira you can configure your workflow transition in such a way that user will be asked to provide a comment when transiting the ticket. Here's an Atlassian article explaining how to do that: https://confluence.atlassian.com/jirakb/how-to-add-a-comment-during-a-transition-779160682.html
But you can also add a file upload functionality there, so, the user can upload a new file together with comment when executing a transition. This file is not a part of the last comment and if you want to send it via email, then use the following code snippet
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$jirassimo.includeAttachmentincludeAttachments("") |
Attaching ALL pdf files uploaded to specific ticket
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$jirassimo.includeAttachmentincludeAttachments("*.pdf") |
Instead of "pdf" you can specify any other file extension
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