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NOTE: This suggestion is for JIRA Cloud. Using JIRA Server? See the corresponding suggestion.
Currently, JIRA does allow to attach file during the Workflow Transition.
It should have an option to Attach Screenshot as well using the clipboard.
Add ability to add attachments during transition to make it more intuitive
Attaching files in transition screen (on Filter Result gadget) failed with Internal Error message
Attach screenshot when creating issue
Attach Screenshot During Workflow Transition (on Filter Result gadget)