[SalesForce] Customer Portal New Case comment notification not working

Working in an org where they are still using the customer portal and are not ready to switch to communities. I have enabled the setting in the Support settings for the cases, as well as the template in the settings for the customer portal as shown below

In Case Support Settings

enter image description here

In Customer Portal Settings

enter image description here

Is there something I am missing? If a user adds a comment internally to a case, whether private or public, the case owner is notified. Its only when a customer adds a case comment through the portal, no notification is sent to the case owner.

I know I can likely bypass this and manually create a workflow to send a notification, but I shouldn't have to and I really want to understand why the native functionality isn't working here.

I am much more of a developer in Salesforce then an admin, so don't know if I am missing some setting somewhere or do not have this configured correctly. Hoping someone see's the error I am making.

EDIT

Per @Ralph's answer, I added some DML options to the Case Comment prior to it's insertion via Apex. 

Database.DMLOptions opts = new Database.DMLOptions();
opts.EmailHeader.triggerAutoResponseEmail = true;
opts.EmailHeader.triggerOtherEmail = true;
opts.EmailHeader.triggerUserEmail = true;

myComment.setOptions(opts);
insert myComment;

This sends an alert, but it send the very basic plain text system email message seen below

enter image description here

Instead of using the template that is specified in the customer portal settings

enter image description here

Anyone know why this is happening?

Best Answer

Two possible issues. If you're working in a sandbox it's possible that non-system emails are disabled. Go to System->Email Administration->Deliverability to check this. Second, if the case comments are created via the API or APEX you'll need to ensure the DMLOptions email header is enabled when inserting the new case comment.

Failing that you may need to contact customer support to troubleshoot further.

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