SMTP anonymous email

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dave...@gmail.com

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Jan 20, 2015, 4:57:57 PM1/20/15
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We are getting the following error when trying to send emails via SMTP. The smtp address, username, and password are set but it seems that anonymous is being used to send the email. (Note the actual emails were replaced with xx...@xxx.com).

2015-01-20 13:47:54, ERROR, queue.EmailQueueManager, error during email send attempt: com.sun.mail.smtp.SMTPSendFailedException: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM

2015-01-20 13:47:54, ERROR, queue.EmailQueueManager, error sending email (530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM
) from: Alert Notification <xx...@xxx.com>, to: xx...@xxx.com, subject: PWM Alert - Configuration Modification, permanent failure, discarding message

Configuration file - (xxxx represent data that was removed for identity purposes)
<setting key="email.smtp.address" syntax="STRING">^M
279 <label>SMTP Email Server Address</label>^M
280 <value><![CDATA[smtp.office365.com]]></value>^M
281 </setting>^M
282 <setting key="email.smtp.username" syntax="STRING">^M
283 <label>SMTP Email Server Username</label>^M
284 <value><![CDATA[xx...@xxxx.com]]></value>^M
285 </setting>^M
286 <setting key="email.smtp.userpassword" syntax="PASSWORD">^M
287 <label>SMTP Email Server Password</label>^M
288 <!--Note: This value is encrypted and can not be edited directly.--> ^M
289 <!--Please use the Configuration Manager GUI to modify this value.-- >^M
290 <value>xxxxxxxxxxx==</value>^M

Menno Pieters

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Jan 20, 2015, 5:23:56 PM1/20/15
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They are probably refusing mail from the xxx.com sex site ;-)

Sorry, just kidding... Try setting the log level to trace and check the mail transaction. Possibly the authentication method required by office365 is not supported.

In the initial greeting, no authentication method is displayed:

220 DB4PR04CA0005.outlook.office365.com Microsoft ESMTP MAIL Service ready at Tue, 20 Jan 2015 22:21:44 +0000
EHLO example.com
250-DB4PR04CA0005.outlook.office365.com Hello [xxx:xxx:xxxx:xxxx::xx]
250-SIZE 78643200
250-PIPELINING
250-DSN
250-ENHANCEDSTATUSCODES
250-STARTTLS
250-8BITMIME
250-BINARYMIME
250 CHUNKING

Could you try enabling SSL/TLS?

- Menno


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