Port 465 seems open, but still cannot send mail

Question

I have opened the port 465 on my server:

iptables -A INPUT -p tcp -m tcp --dport 465 -j ACCEPT
iptables-save | sudo tee /etc/sysconfig/iptables
service iptables restart

And I can see the port is ACCEPT when I run iptables -L -n

But still when I try to send mail:

$mail = new PHPMailer ();
$mail->IsSMTP ();
$mail->SMTPDebug = 1;
$mail->SMTPAuth = true;
$mail->SMTPSecure = 'ssl';
$mail->Host = 'smtp.gmail.com';
$mail->Port = 465;
$mail->Username = "gmailusername";
$mail->Password = "gmailpassword";
$mail->SetFrom ( $from, $title );
$mail->Subject = $subject;
$mail->Body = $body;
$mail->AddAddress ( $to );
$mail->Send();

I get the following error:

SMTP -> ERROR: Failed to connect to server: Connection timed out (110)
<br />The following From address failed: gmailusername : Called Mail() without being connected

Any help would be appreciated!

Out of curiosity is your username `gmailusername` and password `gmailpassword`? — Jonny Henly, Dec 08 '14 at 08:02
Does your firewall really do egress filtering? I'd suggest using TLS on 587 rather than the obsolete SSL on 465. You can always check if it's your firewall simply by disabling it completely for a moment. Set `SMTPDebug = 4` to get connection info. — Synchro, Dec 08 '14 at 09:04
So I disabled the firewall and I still get the same error. What else can it be? — dsthetics, Dec 08 '14 at 13:47

score 2 · Accepted Answer · answered Dec 13 '14 at 08:18

2

Turns out, digitalocean had blocked sending emails for new users. Contacted them and now it's working. Hope this helps someone.

answered Dec 13 '14 at 08:18

dsthetics

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score 0 · Answer 2 · edited May 23 '17 at 12:29

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please go through http://aldrin.aquisap.info/2012/08/26/wp-mail-smtp-in-wordpress-hosted-by-bluehost/ or SMTP ERROR: Failed to connect to server: Connection timed out (110) with PHPMailer and Outlook SMTP.. i guess this is related to your error.

edited May 23 '17 at 12:29

Community

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answered Dec 08 '14 at 08:08

mayur lagad

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Jonny Henly · Answer 3 · 2014-12-08T08:22:25.430

Google's SMTP server requires authentication, so here's how to set it up:

SMTP server (i.e., outgoing mail): smtp.gmail.com
SMTP username: Your full Gmail or Google Apps email address (e.g. example@gmail.com or example@yourdomain.com)
SMTP password: Your Gmail or Google Apps email password
SMTP port: 465
SMTP TLS/SSL required: yes
In order to store a copy of outgoing emails in your Gmail or Google Apps Sent folder, log into your Gmail or Google Apps email Settings and:
Click on the Forwarding/IMAP tab and scroll down to the IMAP Access section: IMAP must be enabled in order for emails to be properly copied to your sent folder.

Sending Limits

Google limits the amount of mail a user can send, via its portable SMTP server. This limit restricts the number of messages sent per day to 99 emails; and the restriction is automatically removed within 24 hours after the limit was reached.

Source: How To Use Google's SMTP Server

Use TLS on 587, not SSL on 465, which has been deprecated for 15 years. — Synchro, Dec 08 '14 at 09:01

Port 465 seems open, but still cannot send mail

3 Answers3

Google's SMTP server requires authentication, so here's how to set it up:

Sending Limits