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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.

duplicates

JRACLOUD-62074 Add ability to add attachments during transition to make it more intuitive

is duplicated by

JRACLOUD-42801 Attaching files in transition screen (on Filter Result gadget) failed with Internal Error message

is related to

JRACLOUD-5015 Attach screenshot when creating issue

JRASERVER-42900 Attach Screenshot During Workflow Transition (on Filter Result gadget)

is superseded by

JRACLOUD-5015 Attach screenshot when creating issue

(2 mentioned in)