you need to look at this magento event sales_order_shipment_save_after
.
So in app/code/local/Namespace/Module/etc/config.xml:
...
<events>
<sales_order_shipment_save_after>
<observers>
<namespace_module>
<type>singleton</type>
<class>Namespace_Module_Model_Observer</class>
<method>autoEmail</method>
</namespace_module>
</observers>
</sales_order_shipment_save_after>
</events>
....
and in app/code/local/Namespace/Module/Model/Observer.php:
<?php
class Namespace_Module_Model_Observer
{
public function autoEmail($observer) {
$shipment = $observer->getEvent()->getShipment();
$order = $shipment->getOrder();
// your email triggering code here.
}
}