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We are trying to get our set up an SMTP function but keep hitting errors with the test email. We even tried both WP-Mail-SMTP and Easy WP SMTP. After talking with our host at WPEngine we couldn't find any issue on their end since they do use OpenSSL and told us to use port 2525 since we are using Outlook. Our IT department also said that port should work just fine and isn't blocked by Outlook. I even used another SMTP hostname of premierdisability-com.mail.protection.outlook.com. However, that one gave the same error but said connection Timed Out instead of Network is unreachable.

The only option I can think of is editing/swapping the class-phpmailer.php and class-smtp.php files with an older version. But Easy WP SMTP says it should be compatible with our setup of WP (WP v4.8, PHP v5.6). Do you think that would be a good option to try or know of anything else to try?

  object(PHPMailer)#1882 (76) {
  ["Version"]=>
  string(6) "5.2.22"
  ["Priority"]=>
  NULL
  ["CharSet"]=>
  string(5) "UTF-8"
  ["ContentType"]=>
  string(10) "text/plain"
  ["Encoding"]=>
  string(4) "7bit"
  ["ErrorInfo"]=>
  string(82) "SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting"
  ["From"]=>
  string(34) "customercare@premierdisability.com"
  ["FromName"]=>
  string(27) "Premier Disability Services"
  ["Sender"]=>
  string(34) "customercare@premierdisability.com"
  ["ReturnPath"]=>
  string(0) ""
  ["Subject"]=>
  string(56) "WP Mail SMTP: Test mail to maolson@premierdisability.com"
  ["Body"]=>
  string(68) "This is a test email generated by the WP Mail SMTP WordPress plugin."
  ["AltBody"]=>
  string(0) ""
  ["Ical"]=>
  string(0) ""
  ["MIMEBody":protected]=>
  string(69) "This is a test email generated by the WP Mail SMTP WordPress plugin.
"
  ["MIMEHeader":protected]=>
  string(405) "Date: Fri, 15 Sep 2017 18:16:49 +0000
To: maolson@premierdisability.com
From: Premier Disability Services 
Subject: WP Mail SMTP: Test mail to maolson@premierdisability.com
Message-ID: <2b81fcc2a1a7b45ecfed265c6f74ed17@premierdisability.com>
X-Mailer: PHPMailer 5.2.22 (https://github.com/PHPMailer/PHPMailer)
MIME-Version: 1.0
Content-Type: text/plain; charset=UTF-8

"
  ["mailHeader":protected]=>
  string(0) ""
  ["WordWrap"]=>
  int(0)
  ["Mailer"]=>
  string(4) "smtp"
  ["Sendmail"]=>
  string(18) "/usr/sbin/sendmail"
  ["UseSendmailOptions"]=>
  bool(true)
  ["PluginDir"]=>
  string(0) ""
  ["ConfirmReadingTo"]=>
  string(0) ""
  ["Hostname"]=>
  string(0) ""
  ["MessageID"]=>
  string(0) ""
  ["MessageDate"]=>
  string(31) "Fri, 15 Sep 2017 18:16:49 +0000"
  ["Host"]=>
  string(18) "smtp.office365.com"
  ["Port"]=>
  string(4) "2525"
  ["Helo"]=>
  string(0) ""
  ["SMTPSecure"]=>
  string(3) "tls"
  ["SMTPAutoTLS"]=>
  bool(false)
  ["SMTPAuth"]=>
  bool(true)
  ["SMTPOptions"]=>
  array(0) {
  }
  ["Username"]=>
  string(34) "customercare@premierdisability.com"
  ["Password"]=>
  string(8) "*******"
  ["AuthType"]=>
  string(0) ""
  ["Realm"]=>
  string(0) ""
  ["Workstation"]=>
  string(0) ""
  ["Timeout"]=>
  int(300)
  ["SMTPDebug"]=>
  bool(true)
  ["Debugoutput"]=>
  string(4) "echo"
  ["SMTPKeepAlive"]=>
  bool(false)
  ["SingleTo"]=>
  bool(false)
  ["SingleToArray"]=>
  array(0) {
  }
  ["do_verp"]=>
  bool(false)
  ["AllowEmpty"]=>
  bool(false)
  ["LE"]=>
  string(1) "
"
  ["DKIM_selector"]=>
  string(0) ""
  ["DKIM_identity"]=>
  string(0) ""
  ["DKIM_passphrase"]=>
  string(0) ""
  ["DKIM_domain"]=>
  string(0) ""
  ["DKIM_private"]=>
  string(0) ""
  ["DKIM_private_string"]=>
  string(0) ""
  ["action_function"]=>
  string(0) ""
  ["XMailer"]=>
  string(0) ""
  ["smtp":protected]=>
  object(SMTP)#1886 (14) {
    ["Version"]=>
    string(6) "5.2.22"
    ["SMTP_PORT"]=>
    int(25)
    ["CRLF"]=>
    string(2) "
"
    ["do_debug"]=>
    bool(true)
    ["Debugoutput"]=>
    string(4) "echo"
    ["do_verp"]=>
    bool(false)
    ["Timeout"]=>
    int(300)
    ["Timelimit"]=>
    int(300)
    ["smtp_transaction_id_patterns":protected]=>
    array(3) {
      ["exim"]=>
      string(21) "/[0-9]{3} OK id=(.*)/"
      ["sendmail"]=>
      string(29) "/[0-9]{3} 2.0.0 (.*) Message/"
      ["postfix"]=>
      string(35) "/[0-9]{3} 2.0.0 Ok: queued as (.*)/"
    }
    ["smtp_conn":protected]=>
    bool(false)
    ["error":protected]=>
    array(4) {
      ["error"]=>
      string(0) ""
      ["detail"]=>
      string(0) ""
      ["smtp_code"]=>
      string(0) ""
      ["smtp_code_ex"]=>
      string(0) ""
    }
    ["helo_rply":protected]=>
    NULL
    ["server_caps":protected]=>
    NULL
    ["last_reply":protected]=>
    string(0) ""
  }
  ["to":protected]=>
  array(1) {
    [0]=>
    array(2) {
      [0]=>
      string(29) "maolson@premierdisability.com"
      [1]=>
      string(0) ""
    }
  }
  ["cc":protected]=>
  array(0) {
  }
  ["bcc":protected]=>
  array(0) {
  }
  ["ReplyTo":protected]=>
  array(0) {
  }
  ["all_recipients":protected]=>
  array(1) {
    ["maolson@premierdisability.com"]=>
    bool(true)
  }
  ["RecipientsQueue":protected]=>
  array(0) {
  }
  ["ReplyToQueue":protected]=>
  array(0) {
  }
  ["attachment":protected]=>
  array(0) {
  }
  ["CustomHeader":protected]=>
  array(0) {
  }
  ["lastMessageID":protected]=>
  string(56) "<2b81fcc2a1a7b45ecfed265c6f74ed17@premierdisability.com>"
  ["message_type":protected]=>
  string(5) "plain"
  ["boundary":protected]=>
  array(3) {
    [1]=>
    string(35) "b1_2b81fcc2a1a7b45ecfed265c6f74ed17"
    [2]=>
    string(35) "b2_2b81fcc2a1a7b45ecfed265c6f74ed17"
    [3]=>
    string(35) "b3_2b81fcc2a1a7b45ecfed265c6f74ed17"
  }
  ["language":protected]=>
  array(19) {
    ["authenticate"]=>
    string(35) "SMTP Error: Could not authenticate."
    ["connect_host"]=>
    string(43) "SMTP Error: Could not connect to SMTP host."
    ["data_not_accepted"]=>
    string(30) "SMTP Error: data not accepted."
    ["empty_message"]=>
    string(18) "Message body empty"
    ["encoding"]=>
    string(18) "Unknown encoding: "
    ["execute"]=>
    string(19) "Could not execute: "
    ["file_access"]=>
    string(23) "Could not access file: "
    ["file_open"]=>
    string(33) "File Error: Could not open file: "
    ["from_failed"]=>
    string(35) "The following From address failed: "
    ["instantiate"]=>
    string(36) "Could not instantiate mail function."
    ["invalid_address"]=>
    string(17) "Invalid address: "
    ["mailer_not_supported"]=>
    string(25) " mailer is not supported."
    ["provide_address"]=>
    string(54) "You must provide at least one recipient email address."
    ["recipients_failed"]=>
    string(45) "SMTP Error: The following recipients failed: "
    ["signing"]=>
    string(15) "Signing Error: "
    ["smtp_connect_failed"]=>
    string(22) "SMTP connect() failed."
    ["smtp_error"]=>
    string(19) "SMTP server error: "
    ["variable_set"]=>
    string(30) "Cannot set or reset variable: "
    ["extension_missing"]=>
    string(19) "Extension missing: "
  }
  ["error_count":protected]=>
  int(2)
  ["sign_cert_file":protected]=>
  string(0) ""
  ["sign_key_file":protected]=>
  string(0) ""
  ["sign_extracerts_file":protected]=>
  string(0) ""
  ["sign_key_pass":protected]=>
  string(0) ""
  ["exceptions":protected]=>
  bool(true)
  ["uniqueid":protected]=>
  string(32) "2b81fcc2a1a7b45ecfed265c6f74ed17"
}
The SMTP debugging output is shown below:

2017-09-15 18:16:49 Connection: opening to smtp.office365.com:2525, timeout=300, options=array (
                                      )
2017-09-15 18:17:59 Connection: Failed to connect to server. Error number 2. "Error notice: stream_socket_client(): unable to connect to smtp.office365.com:2525 (Network is unreachable)
2017-09-15 18:17:59 SMTP ERROR: Failed to connect to server: Network is unreachable (101)
2017-09-15 18:17:59 SMTP connect() failed. https://github.com/PHPMailer/PHPMailer/wiki/Troubleshooting
  • Try this on your server telnet smtp.office365.com 2525, make sure that host is accepting connections, in my machine, it doesn't. – Samuel Elh Sep 15 '17 at 23:39
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I just discovered we had this issue yesterday. Successfully setup mailgun this morning. It's free for less than 10,000 emails per month.

  • note for the future, I will keep this answer around (not that it depends on me ;) ) but generally "use a different tool", one which is not trivial to use, is not a very good answer. – Mark Kaplun Sep 18 '17 at 3:02
  • Ah yes - I should have posted that WP engine are blocking ports 25 465 587. Port 2525 is suggested if your SMTP provider supports it. WP Engine only allow Gmail on 465 and 587. That's why I looked elsewhere and found mailgun. – Loudsy Sep 19 '17 at 3:10
  • now it is 10 times better ;) – Mark Kaplun Sep 19 '17 at 4:14
  • The only issue with using MailGun is that while we only expect to get 100 emails a month, they don't want to put the debut card on things like this. And Mail gun requires a card to be put in first. – IamDade89 Oct 2 '17 at 16:07

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