To get email to work you need to do the following:
For each Practice Location, define the various email related parameters (ie Mail Host, Port, Username, Password, and Connection Security). You need to do this for each Location even if the settings are the same for each.
Then define the Email contact, and if appropriate, add different ones for each applicable purpose (eg Billing, Correspondence, Reminder). Note that you can set the Email contacts at either the Practice or Location level. If you set them at the Location level, these will be used in preference to the those set at the Practice level.
If you are having problems, you can enable debugging by editing the mailSender bean in :
$TOMCAT_HOME/webapps/openvpms/WEB-INF/openvpms-web-app.xml
Change
<bean id="mailSender" class="org.openvpms.web.component.service.MailService" scope="prototype"/>
to
<bean id="mailSender" class="org.openvpms.web.component.service.MailService" scope="prototype">
<property name="javaMailProperties">
<props>
<prop key="mail.smtps.debug">true</prop>
</props>
</property>
</bean>
You can then look in the log at $TOMCAT_HOME/openvpms.log for the debug output.