Time out error during email test

Hi Chris. A connection timeout implies that the client (your WordPress) was unable to establish a TCP connection to the server. This probably has nothing to do with the plugin. If you typed in the server (smtp.gmail.com) and port (465) correctly, then I would say that there is a firewall on your WordPress server preventing outbound connection requests on port 465.

Do you have terminal access to the server your WordPress is installed to? And easy way to tell if the port is open is to try from telnet like this:

Jasons-MBP:~ jasonhendriks$ telnet smtp.gmail.com 465
Trying 173.194.76.108...
Connected to gmail-smtp-msa.l.google.com.
Escape character is '^]'.

If you see “Connected”, then the port is open and I have some serious troubleshooting to do! But if your server can’t make a connection to Gmail because of a firewall or other network issue you will see a Timeout like this:

Jasons-MBP:~ jasonhendriks$ telnet smtp.gmail.com 466
Trying 74.125.29.109...
telnet: connect to address 74.125.29.109: Operation timed out

Obviously you need to run the telnet commands from the server where your WordPress is installed, not your local computer.

Chris, I have some bad news. Hostmonster prevents outgoing connections on port 465 “for spam reasons”. I’ve copied the transcript of the chat I had with their tech support below.

But they provide an internal mail server for sending email. There really isn’t any need for you to use the plugin. If your worry is that they have access to your outgoing email, I suggest switching to a different host.

—->8——–>8——–>8——–>8——–>8——–>8——–>8——–>8——–>8—-

Chat ID: 3811817. Question: Provider: HostMonster – My Domain is: “Not Specified” Hello, I have written a WordPress plugin for accessing gmail via OAuth2. One of my users has their WordPress site hosted with you, and claims that the plugin errors out with “Connection timeout” when they attempt to send mail. My question to you: Are there any cases where you, HostMonster, prevent a hosted application from creating outbound TCP connections on port 465? Specifically to smtp.gmail.com If the answer is no, can I get access to a similar service at HostMonster for a period of about 1-2 weeks so that I can do troubleshooting? Thank-you
9:34:16pmJohnathan
Hello! Thank you for contacting support today. I’m handling multiple chats at once so responses may be slightly delayed.
9:34:18pmJohnathan
For account security would you please validate your account? Can you please provide me with either the last 4 of your account password, full pin number, or the last 4 of the credit card(or full paypal invoice number) used to sign up the account?
9:34:37pmJason
Hello Johnathan. I don’t have an account with host monster.
9:34:37pmJohnathan
What is th eprimary domain on your account?
9:36:12pmJohnathan
Well honestly the only thing I could suggest would be to sign up for an account and then cancel it out when your testing is completed. We don’t really offer any testing environments that I’m aware of. I wouldn’t think that TCP for port 465 would get blocked
9:36:22pmJohnathan
That port is open by default on all accounts
9:37:20pmJason
Ok. If I have to sign up, do I need to know the specific hosting plan of the user with the issue? Or are all plans the same .. technology-wise.
9:37:51pmJohnathan
Quick question, that outbound connection, is it trying to use gmail as the smtp server for a scripted mail?
9:38:09pmJohnathan
Or just sending to it from the local server
9:38:10pmJason
yes, that’s right. smtp.gmail.com on port 465.
9:38:28pmJohnathan
That won’t work in a shared environment with our hosting
9:38:38pmJason
Ah, is that so. Why is that?
9:38:41pmJohnathan
Any scripted mail has to use the local server to send with
9:38:53pmJohnathan
It’s due to spam reasons
9:40:21pmJason
Thank-you very much, Johnathan. You’ve been very helpful. Not the answer I was hoping to give back to the user. But you did save me some needless troubleshooting 😉
9:40:47pmJohnathan
You’re welcome Jason