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Adding attachments to a comment or description field on transition screen

Does anyone else find that the inability to add attachments directly into a comment from a transition screen is detrimental to your workflow? In both software and service, this causes unique problems. 

Software:

In my software tickets to my dev team, we almost always have multiple markups for revisions that we're passing back and forth in the life of the ticket. If, when transitioning the issue, I just add an attachment to the attachment field, the attachment can sometimes get missed or the team might open and refer to the wrong one. 

My workaround has been to transition the issue first and then go back into the issue and edit the comment to add the attachment there. 

Service:

In my service tickets to our agency and client partners, we may sometimes need to send markups or assets via attachments which must be done via the comment for the portal user to see them. However, the only way I can add an attachment to the comment section is if I have the attachments field on the screen as well and then drag the attachment into the comment section. This presents so many opportunities for mistakes. 

1. A service team member forgets and only adds the attachment to the attachment field

2. When dragging, the attachment only adds to the attachment field and does not correctly embed in the comment section

I'd love thoughts and, if you're having similar frustrations, please interact with this post so we can encourage Atlassian to address!

*Note: I do know that there is an extension which can allow portal users to more easily see attachments, but I can't justify asking my small company to pay $58 more a month just for use of attachments that should come standard.

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