Why do attachments sometimes not get added in Issue Event notifications

It boils down to when during the 'Done' transition dialog, the files are uploaded:

IF the files are uploaded, and then a comment is added that takes more than 30S to think/type, the attachments will NOT be found (it appears they get a timestamp the moment they are uploaded as opposed to when the action is submitted).

Repeating the above with a simple text message, submitting within 30S WILL show the attachment as found.

Its not perfect, but at least an explanation. Theoretically, uploaded attachments should get the timestamp of 'when' the submit button was made, which would make all Event-Related time-boxing much more accurate.