I have insight into what works and doesn't work sending through Gmail.
I found a strange bug in my version of the DNS-323 (Firmware 1.09). If I use correct email settings, I can send test messages, and alerts work. If I use certain incorrect settings, then I get failures. But if I use special incorrect settings, I crash the administrative web server, essentially freezing it, perhaps due to a blocked process.
I tried several configurations. In each case, I included these settings:
username: myaccount@gmail.com
password: magicpassword
sender email: myaccount@gmail.com
receiver email: myaccount@gmail.com
smtp authentication: check
The correct settings finished with this:
smtp server: smtp.gmail.com, port: 587
Settings that resulted in failure message finished with this:
smtp server: smtp.googlemail.com, port: 587
Settings that resulted in a crash finished with either of these:
smtp server: smtp.googlemail.com, port: 465
smtp server: smtp.gmail.com, port: 465
I'm surprised to find that these result in a crash, since the port 465 settings were taken from Google's documentation of how to set up outgoing email.
The crashed web server won't come up until it is restarted. Most people will need to reboot the DNS 323 for this. Those of us with ffp installed and ssh access can go in and restart it as follows:
# killall webs
# /web/webs &
By the way, I've seen many people complain in online forums that no logging is available to inform them of what causes their test to fail. If you can log in through ssh and watch the console, then you'll see the errors in the output. For example, with smtp.google.com.com on 587, I saw this:
msmtp: the server does not support authentication
msmtp: could not send mail (account default from /etc/.msmtprc)
Error sending message, child exited 69 (Service unavailable.).
And when I tried testing with smtp.gmail.com on 587 but without checking the box for smtp authentication, I saw this:
msmtp: envelope from address myaccount@gmail.com not accepted by the server
msmtp: server message: 530 5.7.0 Must issue a STARTTLS command first. c18sm589580ana.27
msmtp: could not send mail (account default from /etc/.msmtprc)
Error sending message, child exited 65 (Data format error.).
Mail Server test fail
However, the only way I know to get these in my output is to first restart the web server from the console. I suppose this makes the process of my ssh session the parent to the web server process.
On the crash, no message is sent to output. Instead, the system freezes.
Interesting!