Title: Send Email Failed
Last modified: August 24, 2016

---

# Send Email Failed

 *  Resolved [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/)
 * Outgoing Mail Server Hostname ————> smtp.gmail.com
 * Port 25 443* 465 587
    Outbound to Internet Open Open Open Open Service Available
   SMTP No No SMTP ID google.com – – google.com STARTTLS No – – No Auth None Yes––
   Yes Login No – – No Plain No – – No CRAM-MD5 No – – No OAuth 2.0 No – – No
 * WP 4.2.1 on LOCALHOST
 * Tried on port 25: Could not open socket
    Tried on port 443: HOST not responding
   Tried on port 465: Could not open socket Tried on port 587: Could not open socket
   Tried on port 587: Unable to connect via TLS
 * 587 Port seems to connect with telnet and openssl
 * Windows firewall disabled / Eset antivirus Disabled
 * CHECKED! (Your PHP configuration is preventing outbound connections)
    CHECKED!(
   Your WordPress configuration is preventing outbound connections)
 * Bufff… Any ideas?
    Maybe an enterprise firewall on the network side is blocking
   me?
 * [https://wordpress.org/plugins/postman-smtp/](https://wordpress.org/plugins/postman-smtp/)

Viewing 15 replies - 1 through 15 (of 23 total)

1 [2](https://wordpress.org/support/topic/send-email-failed/page/2/?output_format=md)
[→](https://wordpress.org/support/topic/send-email-failed/page/2/?output_format=md)

 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125047)
 * Ya, your results don’t make sense.
    - Your server ID is google.com BUT STARTTLS is No, and Auth None is Yes. That
      would never happen with the real Gmail server.
    - And you couldn’t create a connection on port 443 to [http://www.googleapis.com](http://www.googleapis.com),
      that almost never happens.
    - Port 465 is open to portquiz.net but not to smtp.gmail.com?
 * You’re not going to be able to send mail via Gmail.
 * From your results I would say you hit a server pretending to be Google, but isn’t.
   Who is your web host/ISP? Your host has obviously redirected your outbound requests.
 * Why don’t you try the test again against the server **mailtrap.io**. It would
   be interesting to see if you get expected results in that case.
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125082)
 * mailtrap.io RESULTS:
 * Port____________25 443 465 587
    Outbound________Open Open Open Open Service_________SMTP
   No SMTP No ID______________mailtrap.io – mailtrap.io – STARTTLS________No – No–
   Auth None____________No – No – Login___________Yes – Yes – Plain___________Yes–
   Yes – CRAM-MD5________Yes – Yes – OAuth 2.0_______No – No –
 * So I understand there´s something between me and smtp.gmail.com
    I must say, 
   by now I´m still in developing stage of our website and it´s stored in my local
   PC using AMPPS. So there is no host provider blocking me (YET), most probably
   it´s something tweaked by the networking genius department of my job.
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125083)
 * Your mailtrap.io results are normal, except, like your Google results, STARTTLS
   has been disabled.
 * It’s a classic man-in-the-middle attack. The only question, has your network 
   been hacked, or is this intentional behaviour imposed by your IT team?
 * See [http://m.slashdot.org/story/209717](http://m.slashdot.org/story/209717)
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125084)
 * As per [https://stomp.colorado.edu/blog/blog/2012/12/31/on-smtp-starttls-and-the-cisco-asa/](https://stomp.colorado.edu/blog/blog/2012/12/31/on-smtp-starttls-and-the-cisco-asa/),
   the Cisco router meddles with the SMTP conversation intentionally. I would love
   to see that conversation. Would it be possible for you to install the Debug plugin,
   enable WP_DEBUG_LOG, enable Trace in Postman’s LogLevel (Advanced tab of the 
   settings), try the connection test again and send me the log file?
 * [https://wordpress.org/plugins/debug/](https://wordpress.org/plugins/debug/)
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125130)
 * For sure! I’ll do it tomorrow. Let me say I get the same results with yahoo and
   hotmail smtps.
    Thanks a lot
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125175)
 * Hi! I did it but no success.
    1- Enable Trace in Postman 2- Install the Debug
   plugin 3- Enable WP_DEBUG_LOG 4- Test connection in POSTMAN
 * …I went to wp-content, but the log file not exist.
    So I checked the wp-config
   and there was:
 * define(‘WP_DEBUG_LOG’, false);
    define(‘WP_DEBUG_DISPLAY’, true);
 * But the option was previously activated in the step 3, anyway I edited it manually,
   run the test again and finally the log file was there.
    I´m trying to understand
   it, it´s quite interesting Do you want to be posted here? Or send you it attached
   in a email?
 * Thanks Thanks!
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125195)
 *     ```
       [14-May-2015 10:28:19 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:19 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:19 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:19 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:21 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: 465
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: 587
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing TCP port: hostname smtp.gmail.com port 587
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing TCP port: hostname smtp.gmail.com port 465
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: testPortQuiz()
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: testPortQuiz()
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: 443
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing TCP port: hostname smtp.gmail.com port 443
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: testPortQuiz()
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: 25
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing TCP port: hostname smtp.gmail.com port 25
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: testPortQuiz()
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => connected to portquiz.net:587
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: smtp.gmail.com:465 => connected to portquiz.net:465
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:465 success=1
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:587 success=1
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 465
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: smtp.gmail.com:443 => connected to portquiz.net:443
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:443 success=1
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 443
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 587
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => connected to portquiz.net:25
   
       [14-May-2015 10:28:21 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:25 success=1
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:21 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 25
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:22 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:22 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: www.googleapis.com
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 443
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 25
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanPortTestAjaxController: testing HTTPS port: hostname www.googleapis.com port 443
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: testHttpPorts()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanPortTestAjaxController: testing SMTP port: hostname smtp.gmail.com port 25
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: testSmtpPorts()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: talkToMailServer()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 587
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanPortTestAjaxController: testing SMTP port: hostname smtp.gmail.com port 587
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: testSmtpPorts()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: talkToMailServer()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 465
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: 
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanPortTestAjaxController: testing SMTP port: hostname smtp.gmail.com port 465
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: testSmtpPorts()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: talkToMailServer()
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => connected to smtp.gmail.com:25
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: smtp.gmail.com:465 => connected to smtp.gmail.com:465
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: www.googleapis.com:443 => Could not connect to ssl://www.googleapis.com:443 because  [0]
   
       [14-May-2015 10:28:22 UTC] DEBUG PostmanPortTestAjaxController: testing port result for www.googleapis.com:443 success=
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => www.googleapis.com
           [hostname_domain_only] => googleapis.com
           [port] => 443
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] =>
       )
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 220 mx.google.com ESMTP bh7sm37438444wjb.8 - gsmtp
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: comparing google.com with gmail.com
   
       [14-May-2015 10:28:23 UTC] DEBUG PostmanPortTest: smtp.gmail.com:25 => domain name: mx.google.com (google.com)
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => tx: EHLO 127.0.0.1
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-mx.google.com at your service, [212.163.73.4]
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-SIZE 35882577
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-8BITMIME
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-STARTTLS
   
       [14-May-2015 10:28:23 UTC] DEBUG PostmanPortTest: smtp.gmail.com:25 => starttls
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-ENHANCEDSTATUSCODES
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-PIPELINING
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250-CHUNKING
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 250 SMTPUTF8
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => tx: STARTTLS
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:25 => rx: 220 2.0.0 Ready to start TLS
   
       [14-May-2015 10:28:23 UTC] ERROR PostmanPortTest: smtp.gmail.com:25 => starttls failed
   
       [14-May-2015 10:28:23 UTC] DEBUG PostmanPortTest: smtp.gmail.com:25 => return true
   
       [14-May-2015 10:28:23 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:25 success=1
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 25
           [protocol] => SMTP
           [secure] =>
           [mitm] =>
           [reported_hostname] => mx.google.com
           [reported_hostname_domain_only] => google.com
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] => 1
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:23 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => connected to smtp.gmail.com:587
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 220 mx.google.com ESMTP yz3sm5006862wjc.19 - gsmtp
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: comparing google.com with gmail.com
   
       [14-May-2015 10:28:24 UTC] DEBUG PostmanPortTest: smtp.gmail.com:587 => domain name: mx.google.com (google.com)
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => tx: EHLO 127.0.0.1
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-mx.google.com at your service, [212.163.73.4]
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-SIZE 35882577
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-8BITMIME
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-STARTTLS
   
       [14-May-2015 10:28:24 UTC] DEBUG PostmanPortTest: smtp.gmail.com:587 => starttls
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-ENHANCEDSTATUSCODES
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-PIPELINING
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250-CHUNKING
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 250 SMTPUTF8
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => tx: STARTTLS
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx: 220 2.0.0 Ready to start TLS
   
       [14-May-2015 10:28:24 UTC] ERROR PostmanPortTest: smtp.gmail.com:587 => starttls failed
   
       [14-May-2015 10:28:24 UTC] DEBUG PostmanPortTest: smtp.gmail.com:587 => return true
   
       [14-May-2015 10:28:24 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:587 success=1
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:24 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 587
           [protocol] => SMTP
           [secure] =>
           [mitm] =>
           [reported_hostname] => mx.google.com
           [reported_hostname_domain_only] => google.com
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] => 1
           [try_smtps] =>
           [success] => 1
       )
   
       [14-May-2015 10:28:32 UTC] DEBUG PostmanPortTest: smtp.gmail.com:465 => return false
   
       [14-May-2015 10:28:32 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:465 success=
   
       [14-May-2015 10:28:32 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:32 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 465
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] => 1
           [success] =>
       )
   
       [14-May-2015 10:28:33 UTC] DEBUG Postman: Postman SMTP v1.6.7 starting
   
       [14-May-2015 10:28:33 UTC] DEBUG PostmanWpMailBinder: Binding to wp_mail()
   
       [14-May-2015 10:28:33 UTC] DEBUG PostmanWpMailBinder: Bound to wp_mail()
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanEmailLogService: Created custom post type
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: Found parameter "hostname"
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: smtp.gmail.com
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: Found parameter "port"
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: 465
   
       [14-May-2015 10:28:33 UTC] DEBUG PostmanPortTestAjaxController: testing SMTPS port: hostname smtp.gmail.com port 465
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTest: testSmtpsPorts()
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTest: talkToMailServer()
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTest: smtp.gmail.com:465 => Could not connect to ssl://smtp.gmail.com:465 because  [0]
   
       [14-May-2015 10:28:33 UTC] DEBUG PostmanPortTestAjaxController: testing port result for smtp.gmail.com:465 success=
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: Ajax response:
   
       [14-May-2015 10:28:33 UTC] TRACE PostmanPortTestAjaxController: Array
       (
           [hostname] => smtp.gmail.com
           [hostname_domain_only] => gmail.com
           [port] => 465
           [protocol] =>
           [secure] =>
           [mitm] =>
           [reported_hostname] =>
           [reported_hostname_domain_only] =>
           [message] =>
           [start_tls] =>
           [auth_plain] =>
           [auth_login] =>
           [auth_crammd5] =>
           [auth_xoauth] =>
           [auth_none] =>
           [try_smtps] =>
           [success] =>
       )
       ```
   
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125196)
 * Better to [email me here](http://www.codingmonkey.ca/contact/). Thank-you!
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125201)
 * Done!
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125204)
 * Got it:
 * > [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx:
   > 250-mx.google.com at your service, [212.163.73.4]
 * So here the server claimed to be Google.
 * > [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => rx:
   > 250-STARTTLS
 * Here the server reported having STARTTLS capability
 * > [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:587 => tx:
   > STARTTLS
   >  [14-May-2015 10:28:24 UTC] TRACE PostmanPortTest: smtp.gmail.com:
   > 587 => rx: 220 2.0.0 Ready to start TLS [14-May-2015 10:28:24 UTC] ERROR PostmanPortTest:
   > smtp.gmail.com:587 => starttls failed
 * And here Postman tried to enable STARTTLS, which is an encryption handshake, 
   and it failed, probably because the certificates the server presented were not
   Google’s.
 * So really really odd 🙂 Show this thread to your IT guys and ask them what they
   make of it!
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125206)
 * Btw, it’s also possible that that is the **real** Gmail site, and the reason 
   you couldn’t connect on 443, 465 or use STARTTLS on 25 or 587 is because of a
   cryptography problem on the client side (ie. your WordPress server). For example,
   the client doesn’t recognize the certificate authority, or the client is running
   a really old version of SSL or a cypher that Google no longer uses.
 * [SSL has taken quite the beating](http://venturebeat.com/2014/10/30/google-plans-to-disable-fallback-to-ssl-3-0-in-chrome-39-and-remove-ssl-3-0-completely-in-chrome-40/)
   lately.
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125261)
 * Talk with IT guys and networking department is not the way.
    In fact I was trying
   it with gmail because they just ignored me when I asked to them to output my 
   emails with his Lotus Domino Server. It was working with gmail a couple of days
   until now. Obviously they are behind.
 * AnyWay I’ve gotten it to work! Yujuuuuu!
    Just setup Postman to Gmail API and
   create a new Client ID and SECRET in google developers site. Voila!
 * JA! 🙂
 * Thanks a lot for your efforts!
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125262)
 * And Knowledge!
 *  Plugin Author [Jason Hendriks](https://wordpress.org/support/users/jasonhendriks/)
 * (@jasonhendriks)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125263)
 * Oh really it works? That’s weird, because the test couldn’t seem to reach [http://www.googleapis.com](http://www.googleapis.com)
   on port 443 ??? Did they open the port?
 *     ```
       [14-May-2015 10:28:22 UTC] TRACE PostmanPortTest: www.googleapis.com:443 => Could not connect to ssl://www.googleapis.com:443 because  [0]
       ```
   
 * Well I’m glad you got it working!
 *  Thread Starter [Lebrack](https://wordpress.org/support/users/lebrack/)
 * (@lebrack)
 * [11 years ago](https://wordpress.org/support/topic/send-email-failed/#post-6125267)
 * I Thought the same. Running the test again offers the same result. So…Who knows!
   (
   Resolved)

Viewing 15 replies - 1 through 15 (of 23 total)

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The topic ‘Send Email Failed’ is closed to new replies.

 * ![](https://s.w.org/plugins/geopattern-icon/postman-smtp_7c7b78.svg)
 * [Postman SMTP Mailer/Email Log](https://wordpress.org/plugins/postman-smtp/)
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 * 23 replies
 * 3 participants
 * Last reply from: [cgreeley40](https://wordpress.org/support/users/cgreeley40/)
 * Last activity: [10 years, 2 months ago](https://wordpress.org/support/topic/send-email-failed/page/2/#post-6125596)
 * Status: resolved