When adding an attachment, the option to add a comment along with it is provided. However in the History Tab panel, this comment is not shown as added.
In the case where the comment and attachment are removed, both show up in the History Tab
I think this boils down to the ability of JIRA to detect and display comment changes/diff, which is not available at the moment - https://jira.atlassian.com/browse/JRA-12400.
I have written a comment history tab which might solve your problem. https://marketplace.atlassian.com/plugins/com.redmoon.jira.commenthistory.commenthistory
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