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Currently Checklist items use the same comment indicator flag as in other forms. It only ticks flagged when any text is entered into the comment. This does not tick flagged if only an attachment is added to a check list item. In addition in the main checklist record, if you click the links button, the item attachments do not list. So as stated no indicator is available to show an attachment is available for the check list item except in the item pop up window. This was also reported in issue PS-39131. As an additional note this functionality really misleads a user by not indicating if an attachment is present on the checklist item. It is understood that the attachment comment could have text entered to tick the item flag; however for a user this is another step and it should indicate automatically that there is an attachment.
