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It would be useful to hide the "Attach context" button the same way as with the submit button or private section (eg. AbstractTaskEditorPage#setNeedsAttachContext). There are connectors out there that do not support file attachements and the button in that case is pretty useless.
Makes sense to me. How about checking if the attachment handler provides an attachment handler that allows uploading for the current task? This would be equivalent to the action enablement for the context menu. Are you interested in providing a patch :)?
Created attachment 166460 [details] patch Here we go ;-)
Created attachment 166461 [details] mylyn/context/zip
Thanks! I have applied the patch.