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Resolved goldenmean
(@goldenmean)

9 years, 9 months ago

I’m having some trouble getting the plugin set up to work with Office365. I have added my IP address to the whitelist in the Office365 admin. It looks like I’m also clear on https://testconnectivity.microsoft.com/ to send email from an external source. All the tests are valid. But I’m still getting an auth error.

Microsoft says that the plugin is sending the credentials in the “wrong” format. Can anyone confirm that this plugin does in fact work with Office365 not on GoDaddy but from Microsoft?

https://www.ads-software.com/plugins/wp-mail-smtp/

Viewing 8 replies - 1 through 8 (of 8 total)

Jason Hendriks

(@jasonhendriks)

9 years, 9 months ago

You need to post your exact error.

Thread Starter

goldenmean

(@goldenmean)

9 years, 9 months ago

Okay, here is the output from the test email. Some information has been redacted to protect my information.

Test Message Sent
The result was:
bool(false)
The full debugging output is shown below:
object(PHPMailer)#54 (69) {
  ["Version"]=>
  string(5) "5.2.7"
  ["Priority"]=>
  int(3)
  ["CharSet"]=>
  string(5) "UTF-8"
  ["ContentType"]=>
  string(10) "text/plain"
  ["Encoding"]=>
  string(4) "8bit"
  ["ErrorInfo"]=>
  string(30) "SMTP Error: data not accepted."
  ["From"]=>
  string(29) "XXXXXXXXXXXXX"
  ["FromName"]=>
  string(22) "XXXXXXXXXXXXX"
  ["Sender"]=>
  string(29) "XXXXXXXXXXXXX"
  ["ReturnPath"]=>
  string(0) ""
  ["Subject"]=>
  string(63) "WP Mail SMTP: Test mail to XXXXXXXXXXXXX"
  ["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(503) "Date: Wed, 10 Jun 2015 17:12:25 +0000
Return-Path:
To: XXXXXXXXXXXXX
From: XXXXXXXXXXXXX
Subject: WP Mail SMTP: Test mail to XXXXXXXXXXXXX
Message-ID: <18df0a633bbd73ec1d5b9b45b50eeda1@xxx.com>
X-Priority: 3
X-Mailer: PHPMailer 5.2.7 (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(0) ""
  ["Host"]=>
  string(18) "smtp.office365.com"
  ["Port"]=>
  string(3) "587"
  ["Helo"]=>
  string(0) ""
  ["SMTPSecure"]=>
  string(3) "tls"
  ["SMTPAuth"]=>
  bool(true)
  ["Username"]=>
  string(27) "XXXXXXXXXXXXX"
  ["Password"]=>
  string(13) "XXXXXXXXXXXXX"
  ["AuthType"]=>
  string(0) ""
  ["Realm"]=>
  string(0) ""
  ["Workstation"]=>
  string(0) ""
  ["Timeout"]=>
  int(10)
  ["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)#77 (12) {
    ["Version"]=>
    string(5) "5.2.7"
    ["SMTP_PORT"]=>
    int(25)
    ["CRLF"]=>
    string(2) "
"
    ["do_debug"]=>
    bool(true)
    ["Debugoutput"]=>
    string(4) "echo"
    ["do_verp"]=>
    bool(false)
    ["Timeout"]=>
    int(10)
    ["Timelimit"]=>
    int(30)
    ["smtp_conn":protected]=>
    resource(324) of type (stream)
    ["error":protected]=>
    array(3) {
      ["error"]=>
      string(23) "DATA END command failed"
      ["smtp_code"]=>
      string(3) "550"
      ["detail"]=>
      string(70) "5.7.60 SMTP; Client does not have permissions to send as this sender
"
    }
    ["helo_rply":protected]=>
    string(192) "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
"
    ["last_reply":protected]=>
    NULL
  }
  ["to":protected]=>
  array(1) {
    [0]=>
    array(2) {
      [0]=>
      string(36) "XXXXXXXXXXXXX"
      [1]=>
      string(0) ""
    }
  }
  ["cc":protected]=>
  array(0) {
  }
  ["bcc":protected]=>
  array(0) {
  }
  ["ReplyTo":protected]=>
  array(0) {
  }
  ["all_recipients":protected]=>
  array(1) {
    ["XXXXXXXXXXXXX"]=>
    bool(true)
  }
  ["attachment":protected]=>
  array(0) {
  }
  ["CustomHeader":protected]=>
  array(0) {
  }
  ["lastMessageID":protected]=>
  string(59) "<18df0a633bbd73ec1d5b9b45b50eeda1@xxx.com>"
  ["message_type":protected]=>
  string(5) "plain"
  ["boundary":protected]=>
  array(3) {
    [1]=>
    string(35) "b1_18df0a633bbd73ec1d5b9b45b50eeda1"
    [2]=>
    string(35) "b2_18df0a633bbd73ec1d5b9b45b50eeda1"
    [3]=>
    string(35) "b3_18df0a633bbd73ec1d5b9b45b50eeda1"
  }
  ["language":protected]=>
  array(18) {
    ["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(15) "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: "
  }
  ["error_count":protected]=>
  int(2)
  ["sign_cert_file":protected]=>
  string(0) ""
  ["sign_key_file":protected]=>
  string(0) ""
  ["sign_key_pass":protected]=>
  string(0) ""
  ["exceptions":protected]=>
  bool(true)
}
The SMTP debugging output is shown below:
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "220 DM2PR07CA0018.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 10 Jun 2015 17:12:25 +0000
"SMTP -> get_lines(): $data is "220 DM2PR07CA0018.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 10 Jun 2015 17:12:25 +0000
"SMTP -> FROM SERVER:220 DM2PR07CA0018.outlook.office365.com Microsoft ESMTP MAIL Service ready at Wed, 10 Jun 2015 17:12:25 +0000
CLIENT -> SMTP: EHLO XXXXXXXXXXXXX.com
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $str is "250-SIZE 157286400
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
"SMTP -> get_lines(): $str is "250-PIPELINING
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
"SMTP -> get_lines(): $str is "250-DSN
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
"SMTP -> get_lines(): $str is "250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $str is "250-STARTTLS
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
"SMTP -> get_lines(): $str is "250-8BITMIME
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
"SMTP -> get_lines(): $str is "250-BINARYMIME
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
"SMTP -> get_lines(): $str is "250 CHUNKING
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING
"SMTP -> FROM SERVER:250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING
CLIENT -> SMTP: STARTTLS
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "220 2.0.0 SMTP server ready
"SMTP -> get_lines(): $data is "220 2.0.0 SMTP server ready
"SMTP -> FROM SERVER:220 2.0.0 SMTP server ready
CLIENT -> SMTP: EHLO xxx.com
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
"SMTP -> get_lines(): $str is "250-SIZE 157286400
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
"SMTP -> get_lines(): $str is "250-PIPELINING
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
"SMTP -> get_lines(): $str is "250-DSN
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
"SMTP -> get_lines(): $str is "250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
"SMTP -> get_lines(): $str is "250-AUTH LOGIN
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
"SMTP -> get_lines(): $str is "250-8BITMIME
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
"SMTP -> get_lines(): $str is "250-BINARYMIME
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
"SMTP -> get_lines(): $data was "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
"SMTP -> get_lines(): $str is "250 CHUNKING
"SMTP -> get_lines(): $data is "250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
"SMTP -> FROM SERVER:250-DM2PR07CA0018.outlook.office365.com Hello [xx.xx.xx.xx]
250-SIZE 157286400
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-AUTH LOGIN
250-8BITMIME
250-BINARYMIME
250 CHUNKING
CLIENT -> SMTP: AUTH LOGIN
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "334 VXNlcm5hbWU6
"SMTP -> get_lines(): $data is "334 VXNlcm5hbWU6
"SMTP -> FROM SERVER:334 VXNlcm5hbWU6
CLIENT -> SMTP: bWFpbG1hbkBhZ2VudHB1Ymxpc2hpbmcuY29t
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "334 UGFzc3dvcmQ6
"SMTP -> get_lines(): $data is "334 UGFzc3dvcmQ6
"SMTP -> FROM SERVER:334 UGFzc3dvcmQ6
CLIENT -> SMTP: U3VtbWVyQWdlbnQxNQ==
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "235 2.7.0 Authentication successful target host SN1PR12MB0157.namprd12.prod.outlook.com
"SMTP -> get_lines(): $data is "235 2.7.0 Authentication successful target host SN1PR12MB0157.namprd12.prod.outlook.com
"SMTP -> FROM SERVER:235 2.7.0 Authentication successful target host SN1PR12MB0157.namprd12.prod.outlook.com
CLIENT -> SMTP: MAIL FROM:
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "250 2.1.0 Sender OK
"SMTP -> get_lines(): $data is "250 2.1.0 Sender OK
"SMTP -> FROM SERVER:250 2.1.0 Sender OK
CLIENT -> SMTP: RCPT TO:
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "250 2.1.5 Recipient OK
"SMTP -> get_lines(): $data is "250 2.1.5 Recipient OK
"SMTP -> FROM SERVER:250 2.1.5 Recipient OK
CLIENT -> SMTP: DATA
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "354 Start mail input; end with .
"SMTP -> get_lines(): $data is "354 Start mail input; end with .
"SMTP -> FROM SERVER:354 Start mail input; end with .
CLIENT -> SMTP: Date: Wed, 10 Jun 2015 17:12:25 +0000
CLIENT -> SMTP: Return-Path:
CLIENT -> SMTP: To: XXXXXXXXXXXXX
CLIENT -> SMTP: From: XXXXXXXXXXXXX
CLIENT -> SMTP: Subject: WP Mail SMTP: Test mail to XXXXXXXXXXXXX
CLIENT -> SMTP: Message-ID: <18df0a633bbd73ec1d5b9b45b50eeda1@xxx.com>
CLIENT -> SMTP: X-Priority: 3
CLIENT -> SMTP: X-Mailer: PHPMailer 5.2.7 (https://github.com/PHPMailer/PHPMailer/)
CLIENT -> SMTP: MIME-Version: 1.0
CLIENT -> SMTP: Content-Type: text/plain; charset=UTF-8
CLIENT -> SMTP: Content-Transfer-Encoding: 8bit
CLIENT -> SMTP:
CLIENT -> SMTP: This is a test email generated by the WP Mail SMTP WordPress plugin.
CLIENT -> SMTP:
CLIENT -> SMTP: .
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "550 5.7.60 SMTP; Client does not have permissions to send as this sender
"SMTP -> get_lines(): $data is "550 5.7.60 SMTP; Client does not have permissions to send as this sender
"SMTP -> FROM SERVER:550 5.7.60 SMTP; Client does not have permissions to send as this sender
SMTP -> ERROR: DATA END command failed: 550 5.7.60 SMTP; Client does not have permissions to send as this sender

CLIENT -> SMTP: QUIT
SMTP -> get_lines(): $data was ""SMTP -> get_lines(): $str is "221 2.0.0 Service closing transmission channel
"SMTP -> get_lines(): $data is "221 2.0.0 Service closing transmission channel
"SMTP -> FROM SERVER:221 2.0.0 Service closing transmission channel

Jason Hendriks

(@jasonhendriks)

9 years, 9 months ago

Your error is:

550 5.7.60 SMTP; Client does not have permissions to send as this sender.

The problem is your Return-Path header.

To quote RFC 5321:

“A message-originating SMTP system SHOULD NOT send a message that already contains a Return-path header field.”

Thread Starter

goldenmean

(@goldenmean)

9 years, 9 months ago

So, the WP-Mail-SMTP plugin is not compatible with this email service? Because, if I leave the “From Email” in the configuration blank, it will just use the default site wide email address. I tested that and got the same error.

Obviously I could modify the plugin to remove the Return-Path header, but that would be effectively hacking the plugin and breaking future upgrades. Is there some other mechanism by which I could override this behavior?

Jason Hendriks

(@jasonhendriks)

9 years, 9 months ago

Either ask the author to fix the plugin or switch to a different one.

Thread Starter

goldenmean

(@goldenmean)

9 years, 9 months ago

That’s what I thought. Thank you for your help.

Thread Starter

goldenmean

(@goldenmean)