A quick post to show how we use Google mail to send mail from Seaside. Here’s our setup for getitmade.com:

1) You need to add WAEmailConfiguration as a configuration ancestor. And you need to add this configuration:

app configuration addParent: WAEmailConfiguration instance.
app
		preferenceAt: #smtpServer put: 'localhost';
		preferenceAt: #smtpPort put: 259;
		preferenceAt: #smtpUsername put: 'support@getitmade.com';
		preferenceAt: #smtpPassword put: 'Rea11yS3cur3'.    "that isn't our password!"

2) You send mails with this string:

GRPlatform current
       seasideDeliverEmailMessage: ((WAEmailMessage
               from: (WAEmailAddress address: 'support@getitmade.com')
                       to: (WAEmailAddress address:  'a.client@astartup.com')
                       subject: 'test')
               body: (WAStringEmailBody string: 'a test')).

it works inside the application (inside a session)… not outside (see below)

3) You need stunnel installed and running. In Ubuntu, you need to make the following changes:

a) replace stunnel.conf with:

client = yes
debug = debug

[smtps]
accept = 127.0.0.1:259
connect = smtp.gmail.com:465

b) create /etc/stunnel/stunnel.pem

$ openssl req -new -x509 -days 3650 -nodes -out stunnel.pem -keyout stunnel.pem

c) enable running:

$ vim /etc/init.d/stunnel4

ENABLED=1

$ vim /etc/default/stunnel4

ENABLED=1

d) restart:

sudo /etc/init.d/stunnel4 restart

If you want to send the mail outside the session for example on a service task you need a mock request context then use something like:

WACurrentRequestContext
		use: IZMockCurrentRequestContext
		during: [
			GRPlatform current
       			seasideDeliverEmailMessage: ((WAEmailMessage
               			from: (WAEmailAddress address: 'support@getitmade.com')
                       		to: (WAEmailAddress address:  toEmailAddress)
                       subject: aSubject)
               body: (WAStringEmailBody string: aBody)) ]