The problem is simply that Launchpad treats each new comment as a
boundary by which to split up notification emails (so if you make
several changes to a bug and add a comment the changes and the comment
will all arrive in the same notification, whereas if you comment first
and then make the changes you'll get separate emails).

Now, from the difficulty-of-implementation point of view I think it's
actually simpler (and more sensible) to support the multiple-
attachments-per-comment use case via addAttachment() (and eventually via
the UI) than it is to change the way Launchpad handles the notification
boundaries. That said, we bundle up notifications for comments imported
from remote bugs, though I can't remember off the top of my head how
that works. It may be that we can re-use that.

I'm marking this as Triaged, Low on the basis that we should probably
add the multiple upload functionality rather than fix this bug.

** Changed in: malone
       Status: Confirmed => Triaged

** Changed in: malone
   Importance: Undecided => Low

-- 
merge multiple attachment emails into one
https://bugs.launchpad.net/bugs/424849
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