Old question, but someone could be interested.
I have gmail account switched to less secure access.
smtp server is smt.gmail.com
To send emails I had to add username and password into the /opt/webwork/webwork2/lib/WeBWorK/ContentGenerator.pm file.
In the lines following
sub createEmailSenderTransportSMTP {
I changed the setting into
host => $ce->{mail}->{smtpServer},
ssl => 'starttls', #$ce->{mail}->{tls_allowed}//0, ## turn off ssl security by default
port => $ce->{mail}->{smtpPort},
timeout => $ce->{mail}->{smtpTimeout},
sasl_username => 'myemail@gmail.com',
sasl_password => 'mypassword',
Here of course you have to use your username and password.
According tom some Debian Howto, 100 email per day is the limit for this access to the smtp server. The reply-to is to not the student's email, but the gmail used for sending messages. This has been mentioned in some other threads.
Hope this helps someone.
Robert