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micthi
Contributor
Contributor

VCSA 6.5 eMail - relay host smtp.office365.com

Hello community,

I have a problem with my vCenter appliance 6.5 (build 6671409) and the email settings for smtp.office365.com.

I have configured the relay host and the sender address under WebClient-Configure-General-Mail.

I have also configured the user, his password und the port 587 under advanced settings (mail.smtp.password, mail.smtp.port, mailsmtp.username).

I've tested those settings in the powershell on my laptop by using the Send-MailMessage ... works fine.

The vCenter-Appliance is not able to send an email and it gives the following error message:

(reason: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [HE1PR0401CA0059.eurprd04.prod.outlook.com])

In /var/log/messages I found:

2017-09-28T12:30:06.639640+00:00 xxxxVC sendmail[58017]: v8SCU6UC058017: from=xxxx@xxxx.xx, size=518, class="0", nrcpts=1, msgid=<201709281230.v8SCU6UC058017@xxxx.xxxx.local>, relay=root@localhost

2017-09-28T12:30:06.715497+00:00 xxxxVC sendmail[58027]: v8SCU6eG058027: from=<xxxx@xxxx.xx>, size=753, class="0", nrcpts=1, msgid=<201709281230.v8SCU6UC058017@xxxx.xxxx.local>, proto=ESMTP, daemon=MTA, relay=xxxx.xxxx.local [127.0.0.1]

2017-09-28T12:30:06.751267+00:00 xxxxVC sendmail[58017]: v8SCU6UC058017: to=yyyy@yyyy.yy, ctladdr=xxxx@xxxx.xx (0/0), delay=00:00:00, xdelay=00:00:00, mailer=relay, pri=30518, relay=[127.0.0.1] [127.0.0.1], dsn=2.0.0, stat=Sent (v8SCU6eG058027 Message accepted for delivery)

2017-09-28T12:30:08.512834+00:00 xxxxVC sendmail[58032]: STARTTLS=client, relay=outlook-emeaeast.office365.com., version=TLSv1.2, verify=FAIL, cipher=ECDHE-RSA-AES256-SHA384, bits=256/256

After this I can open the message in folder /var/spool/mqueue:

root@xxxxVC [ /var/spool/mqueue ]# ls -l

total 8

-rw------- 1 root root 2449 Sep 28 12:30 dfv8SCUDeG058032

-rw------- 1 root root  862 Sep 28 12:30 qfv8SCUDeG058032

Content of Message dfv8SCUDeG058032:

This is a MIME-encapsulated message

--v8SCUDeG058032.1506601813/xxxx.xxxx.local

The original message was received at Thu, 28 Sep 2017 12:30:06 GMT

from xxxx.xxxx.local [127.0.0.1]

   ----- The following addresses had permanent fatal errors -----

<yyyy@yyyy.yy>

    (reason: 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [HE1PR0102CA0036.eurprd01.prod.exchangelabs.com])

   ----- Transcript of session follows -----

... while talking to outlook-emeaeast.office365.com.:

>>> MAIL From:<xxxx@xxxx.xx> SIZE=983 AUTH=<>

<<< 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [HE1PR0102CA0036.eurprd01.prod.exchangelabs.com]

554 5.0.0 Service unavailable

--v8SCUDeG058032.1506601813/xxxx.xxxx.local

Content-Type: message/delivery-status

Reporting-MTA: dns; xxxx.xxxx.local

Received-From-MTA: DNS; xxxx.xxxx.local

Arrival-Date: Thu, 28 Sep 2017 12:30:06 GMT

Final-Recipient: RFC822; yyyy@yyyy.yy

Action: failed

Status: 5.7.57

Diagnostic-Code: SMTP; 530 5.7.57 SMTP; Client was not authenticated to send anonymous mail during MAIL FROM [HE1PR0102CA0036.eurprd01.prod.exchangelabs.com]

Last-Attempt-Date: Thu, 28 Sep 2017 12:30:13 GMT

--v8SCUDeG058032.1506601813/xxxx.xxxx.local

Content-Type: message/rfc822

Return-Path: <xxxx@xxxx.xx>

Received: from xxxx.xxxx.local (xxxx.xxxx.local [127.0.0.1])

        by xxxx.xxxx.local (8.15.2/8.15.2) with ESMTP id v8SCU6eG058027

        for <yyyy@yyyy.yy>; Thu, 28 Sep 2017 12:30:06 GMT

Received: (from root@localhost)

        by xxxx.xxxx.local (8.15.2/8.15.2/Submit) id v8SCU6UC058017;

        Thu, 28 Sep 2017 12:30:06 GMT

Date: Thu, 28 Sep 2017 12:30:06 GMT

Message-Id: <201709281230.v8SCU6UC058017@xxxx.xxxx.local>

To: yyyy@yyyy.yy

From: xxxx@xxxx.xx

Subject: [VMware vCenter - Alarm VM shutdown] Guest OS shut down for Win10Pro_xx on yyyyy.yyyyy.local in yyyyyDC

Content-type: text/plain

Target: Win10Pro_xx

Previous Status: Green

New Status: Red

Alarm Definition:

([Event alarm expression: Guest OS shut down; Status = Red])

Event details:

Guest OS shut down for Win10Pro_xx on yyyyy.yyyyy.local in yyyyyDC

--v8SCUDeG058032.1506601813/xxxx.xxxx.local--

Is there anybody outthere who have the mesaging system running with VCSA6.5 and smtp.office365.com ?

If so, please help.

Thank you

Michael

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1 Reply
AishR
VMware Employee
VMware Employee

Sharing this KB hoping that this would help in narrowing down the issue. Support for SMTP authentication and STARTTLS in the vCenter Server and vCenter Server Appliance 5.x ...

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