SOLVED Outbound email with Google

[scottharvey]

I am trying to set up outgoing email using Google and I'm getting a Connection timeout error.

Is there any way to determine what the problem is?

[nebulon]

Can you verify, that you can reach the smtp.gmail.com server on port 587 just fine on the server? This can be tested on a ssh connection to your server and then attempting telnet smtp.gmail.com 587

Also you might want to take a look at the system logs at journatlct list box, maybe they give more hints.

[scottharvey]

Here are the logs when I try to connect to the server, I've manually changed my logs to point to example.com

Aug 25 00:04:00 my.example.com node[23958]: Sat, 25 Aug 2018 00:03:59 GMT connect-lastmile Bad Request : Connection timeout
Aug 25 00:04:00 my.example.com node[23958]: Box POST /api/v1/mail/example.com/relay 400 5003.952 ms - 64
Aug 25 00:04:00 my.example.com node[23958]: box:scheduler sync: synchronizing global state with installed app state
Aug 25 00:04:00 my.example.com node[23958]: box:scheduler sync: done

When trying to telnet the command just freezes on the following

root@my:/home# telnet smtp.gmail.com 587
Trying 74.125.24.108...
Trying 74.125.24.109...

[nebulon]

If you can ping those IPs (ping 74.125.24.108) successfully, then this is most likely a firewall issue. May it be possible that your VPS provider blocks outbound connections to that port?

[girish]

@scottharvey Are you on Google Cloud?

[scottharvey]

@girish I am using Digital Ocean, I found someone suggesting to contact Digital Ocean support in order to open port 587. I sent them an email and I'm just waiting for a reply.

[scottharvey]

After contacting Digital Ocean support and answering a few questions about my email usage they unblocked port 587 so I can send email now. Thanks for the help.