Test Message Sent The result was: bool(false) The full debugging output is shown below: object(PHPMailer)#6740 (75) { ["Version"]=> string(6) "5.2.14" ["Priority"]=> NULL ["CharSet"]=> string(5) "UTF-8" ["ContentType"]=> string(10) "text/plain" ["Encoding"]=> string(4) "8bit" ["ErrorInfo"]=> string(35) "SMTP Error: Could not authenticate." ["From"]=> string(34) "swisscomply@digitale.mehrwerte.net" ["FromName"]=> string(11) "SwissComply" ["Sender"]=> string(0) "" ["ReturnPath"]=> string(0) "" ["Subject"]=> string(46) "WP Mail SMTP: Test mail to martin@herrhein.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(398) "Date: Tue, 27 Sep 2016 19:52:46 +0000 To: martin@herrhein.com From: SwissComply Subject: WP Mail SMTP: Test mail to martin@herrhein.com Message-ID: <854637d79de67371cc50208a6300d624@www.swisscomply.ch> X-Mailer: PHPMailer 5.2.14 (https://github.com/PHPMailer/PHPMailer) MIME-Version: 1.0 Content-Type: text/plain; charset=UTF-8 Content-Transfer-Encoding: 8bit " ["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) "Tue, 27 Sep 2016 19:52:46 +0000" ["Host"]=> string(41) "lvps87-230-85-137.dedicated.hosteurope.de" ["Port"]=> string(3) "465" ["Helo"]=> string(0) "" ["SMTPSecure"]=> string(0) "" ["SMTPAutoTLS"]=> bool(true) ["SMTPAuth"]=> bool(true) ["SMTPOptions"]=> array(0) { } ["Username"]=> string(34) "swisscomply@digitale.mehrwerte.net" ["Password"]=> string(11) "XXXXXX" ["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) "" ["action_function"]=> string(0) "" ["XMailer"]=> string(0) "" ["smtp":protected]=> object(SMTP)#6725 (13) { ["Version"]=> string(6) "5.2.14" ["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_conn":protected]=> NULL ["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(19) "martin@herrhein.com" [1]=> string(0) "" } } ["cc":protected]=> array(0) { } ["bcc":protected]=> array(0) { } ["ReplyTo":protected]=> array(0) { } ["all_recipients":protected]=> array(1) { ["martin@herrhein.com"]=> bool(true) } ["RecipientsQueue":protected]=> array(0) { } ["ReplyToQueue":protected]=> array(0) { } ["attachment":protected]=> array(0) { } ["CustomHeader":protected]=> array(0) { } ["lastMessageID":protected]=> string(53) "<854637d79de67371cc50208a6300d624@www.swisscomply.ch>" ["message_type":protected]=> string(5) "plain" ["boundary":protected]=> array(3) { [1]=> string(35) "b1_854637d79de67371cc50208a6300d624" [2]=> string(35) "b2_854637d79de67371cc50208a6300d624" [3]=> string(35) "b3_854637d79de67371cc50208a6300d624" } ["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) "854637d79de67371cc50208a6300d624" } The SMTP debugging output is shown below: 2016-09-27 19:52:46 Connection: opening to lvps87-230-85-137.dedicated.hosteurope.de:465, timeout=300, options=array ( ) 2016-09-27 19:52:46 Connection: opened 2016-09-27 19:57:46 SMTP -> get_lines(): $data is "" 2016-09-27 19:57:46 SMTP -> get_lines(): $str is "" 2016-09-27 19:57:46 SMTP -> get_lines(): timed-out (300 sec) 2016-09-27 19:57:46 SERVER -> CLIENT: 2016-09-27 19:57:46 CLIENT -> SERVER: EHLO www.swisscomply.ch 2016-09-27 19:57:46 SMTP -> get_lines(): $data is "" 2016-09-27 19:57:46 SMTP -> get_lines(): $str is "454 TLS connection failed: error:140760FC:SSL routines:SSL23_GET_CLIENT_HELLO:unknown protocol (#4.3.0) " 2016-09-27 19:57:46 SERVER -> CLIENT: 454 TLS connection failed: error:140760FC:SSL routines:SSL23_GET_CLIENT_HELLO:unknown protocol (#4.3.0) 2016-09-27 19:57:46 SMTP ERROR: EHLO command failed: 454 TLS connection failed: error:140760FC:SSL routines:SSL23_GET_CLIENT_HELLO:unknown protocol (#4.3.0) 2016-09-27 19:57:46 CLIENT -> SERVER: HELO www.swisscomply.ch 2016-09-27 19:57:46 SERVER -> CLIENT: 2016-09-27 19:57:46 SMTP ERROR: HELO command failed: 2016-09-27 19:57:46 SMTP Error: Could not authenticate. 2016-09-27 19:57:46 SMTP NOTICE: EOF caught while checking if connected 2016-09-27 19:57:46 Connection: closed 2016-09-27 19:57:46 SMTP Error: Could not authenticate.