"Acknowledge requester by e-mail when the request is updated" Does not work properly

"Acknowledge requester by e-mail when the request is updated" Does not work properly

This notification never works properly.  When assign a technician, and I can see in the history that the request has been updated, the requester never gets an email notifying them about the technician assignment.  It's not until the request is closed that the "request updated" email goes out, so the requester ends up getting 2 emails at the exact same time; one saying it's updated, one stating it's closed.
 
Why won't the ServiceDesk notify our requesters when a technician is assigned?  We want it to email them when one is assigned, and then send them only one email when it's closed, not two.

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