Unable to send after upgrade to 3.2.4

ℹ️ Support
1

We use PHPlist to send out a newsletter monthly and it was working fine until the upgrade to 3.2.4. I am trying to use Secure SMTP but it doesn’t seem to want to connect to our mail server. The server is housed on-site so I have full control over it’s settings. We also recently upgraded it to use only TLS1.1 or above. Could this have caused a conflict and is there a way to tell phplist which encryption and connection port to use? Thanks for any help you can give me.

2

@Dougster There is a new config setting in phplist 3.2.4 for phpmailer to output debug information when sending using SMTP.

See the section in config_extended.php but add to your config file with a level of 2. That will provide some output when you send a test message

## SMTP debugging
# Enable debugging output by phpmailer when sending test emails
# See https://phpmailer.github.io/PHPMailer/classes/PHPMailer.html#property_SMTPDebug
# define('PHPMAILER_SMTP_DEBUG', 0);
3

Yes, I turned it to level 5 already and get the following:

Connection: opening to mail.monicals.com:587, timeout=30, options=array ()
SMTP ERROR: Failed to connect to server: Connection timed out (110)
SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

4

When I try this with SSL on port 465, I get this:

Connection: opening to ssl://mail.monicals.com:465, timeout=5, options=array ()
SMTP ERROR: Failed to connect to server: (0)
SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting

5

And if I try to use port 25 with tls:

Connection: opening to mail.monicals.com:25, timeout=15, options=array ()
Connection: opened
SMTP -> get_lines(): $data is ""
SMTP -> get_lines(): $str is "220 mail.monicals.com ESMTP ready"
SERVER -> CLIENT: 220 mail.monicals.com ESMTP ready
CLIENT -> SERVER: EHLO mail.monicals.com
SMTP -> get_lines(): $data is ""
SMTP -> get_lines(): $str is "250-mail.monicals.com"
SMTP -> get_lines(): $data is "250-mail.monicals.com"
SMTP -> get_lines(): $str is "250-AUTH CRAM-MD5 DIGEST-MD5"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5"
SMTP -> get_lines(): $str is "250-STARTTLS"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS"
SMTP -> get_lines(): $str is "250-ENHANCEDSTATUSCODES"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES"
SMTP -> get_lines(): $str is "250-8BITMIME"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES250-8BITMIME"
SMTP -> get_lines(): $str is "250-PIPELINING"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES250-8BITMIME250-PIPELINING"
SMTP -> get_lines(): $str is "250-ETRN"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES250-8BITMIME250-PIPELINING250-ETRN"
SMTP -> get_lines(): $str is "250-DSN"
SMTP -> get_lines(): $data is "250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES250-8BITMIME250-PIPELINING250-ETRN250-DSN"
SMTP -> get_lines(): $str is "250 HELP"
SERVER -> CLIENT: 250-mail.monicals.com250-AUTH CRAM-MD5 DIGEST-MD5250-STARTTLS250-ENHANCEDSTATUSCODES250-8BITMIME250-PIPELINING250-ETRN250-DSN250 HELP
CLIENT -> SERVER: STARTTLS
SMTP -> get_lines(): $data is ""
SMTP -> get_lines(): $str is "220 2.0.0 Ready to start TLS"
SERVER -> CLIENT: 220 2.0.0 Ready to start TLS
SMTP Error: Could not connect to SMTP host.
SMTP NOTICE: EOF caught while checking if connected
Connection: closed

6

Are you sure which ports are open to the mail server?
In principle you need only to set the TLS/SSL setting and the port appropriately

## you can set this to send out via a different SMTP port
# define('PHPMAILERPORT',25);

# to use SSL/TLS when sending set this value
# it can either be "ssl" or "tls", nothing else
# define("PHPMAILER_SECURE",'ssl');

But there is a new setting in phpmailer to automatically start tls that has caused me a problem.
This line in file class.phplistmailer.php now enables that. You could also try setting that to false.

    $this->SMTPAutoTLS = true;