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Sometimes you have to attach several related files to a task, or a new version of a previously attached file. Similar to commit comments, it would be useful to be able to reuse a previous description when attaching a file, possibly after editing it. There could be a dropdown to select from recently used descriptions. Descriptions could come entirely from local history or they could be pulled from existing attachments on the task.
You could define comment templates but I agree that having access to comment history makes more sense in most cases.
Mylyn has been restructured, and our issue tracking has moved to GitHub [1]. We are closing ~14K Bugzilla issues to give the new team a fresh start. If you feel that this issue is still relevant, please create a new one on GitHub. [1] https://github.com/orgs/eclipse-mylyn