Exchange 2016 issue

KevinL 1 Reputation point
2021-11-15T15:35:27.033+00:00

I am at my wits end. We have a Exchange 2016 installation (CU21) runningo n a Server 2016 VM.

For most intents it's works fine for our company, however there is one small hiccup, and my supervisor refuses to let it drop.

Our phone system (FreePBX/Asterisk) Is setup so that after hours, requests for tech support are sent to a distribution group on the Exchange server. This message is sent each time without fail, and we have never had a problem with it. This distribution list then is supposed to forward this message to the technicians cells phones and such. One of our techs is on T-Mobile, and receives these messages just fine. The other techs are on Verizon and never seem to get the messages.

The messages are text and attached VM. We have verified the emails being sent to are the ones for external email to text message addresses. When we try and test this, we can send messages from email to them singly, but for some reason when it's in this group, it fails every time. My boss has had me chasing this for 2 months now, and I cannot seem to find issue other than something on Verizons end must not like messages with BCC or CC in them.

I can find no issues with the settings. All our other distro group emails work ok, this is the only one that fails. We have tried re-creating it with the same result.

Any suggestions?

Exchange Server Management
Exchange Server Management
Exchange Server: A family of Microsoft client/server messaging and collaboration software.Management: The act or process of organizing, handling, directing or controlling something.
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3 answers

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  1. Andy David - MVP 142.2K Reputation points MVP
    2021-11-15T17:07:21.273+00:00

    Could be failing SPF when sent to the DL from that phone system.

    Can you add a regular external email address to that DL and see if it gets delivered or check the headers of the one that works for T-Mobile?


  2. KevinL 1 Reputation point
    2021-11-17T20:39:06.39+00:00

    We have finally completed an external mail test.
    The test passed, and the email with attachment came through to thier email within about 30 seconds of leaving the test message.

    Here si the 'original message' as gmail presented it with headers

    Delivered-To: <withheld>@Stuff .com
    Received: by 2002:adf:fb09:0:0:0:0:0 with SMTP id c9csp1418712wrr;
    Wed, 17 Nov 2021 12:17:59 -0800 (PST)
    X-Google-Smtp-Source: ABdhPJzguDLlGw+GGvHCmOgmCeSUp0xM4E2jOVJ8Fv3Y3RlAoGzGmBcNzSrnaMsdiQ+iNcqHIo2+
    X-Received: by 2002:a05:6638:1382:: with SMTP id w2mr15671616jad.50.1637180278868;
    Wed, 17 Nov 2021 12:17:58 -0800 (PST)
    ARC-Seal: i=1; a=rsa-sha256; t=1637180278; cv=none;
    d=google.com; s=arc-20160816;
    b=NOD11AbKQ7OdThcwTzlYzTKca/BX/NIN8dCGOIvqpjqilj27a6+FBd7KZ+ZjCqLsQN
    ZSt9h8PXwGdiL0hUWY1KxiKUQS+2xKxQ7oaXtSpdrzPsnayaplAjOAzZRBkCWIYjHwYE
    ND/2iF487t+qOM5uX/JhnAuahbhaBIheBFNEvtys0AH44yfrvrEXWUnZyy/aGhz5yWq1
    SCmv7Ah3Hu8SSCmA04CQNOoFL6ZqoV+bX+KwYLJxKexrr6UbyBRmnSwCT9VCa78o5EZ5
    aC55pd3zN4Da0CjC269iimdclXaoA69WTovypVhE8QlUrhDD85z7E4IWb5DOH/JABzo/
    P7xQ==
    ARC-Message-Signature: i=1; a=rsa-sha256; c=relaxed/relaxed; d=google.com; s=arc-20160816;
    h=mime-version:message-id:subject:to:from:date;
    bh=DHw/vB282t4X3dJKNBiVQkONp6InJ3U0QcqT96Rexn0=;
    b=nHh2jAjL7iA3Z9poKfzp3XaX6WlTK3UDwYd8LQiZszBPU754jki2WpCmgmAYMNRQh2
    Nt2GPnwk7nzHaIT2zRZkSBTI841E7BWvr5S1GtM5Bx1vS3BEjvFsjmDTLtTIVB0FwQSU
    /xOxXohpCZkEpo54Z6BhdtdmIMbcnnRHSoPDRsc31TxZXc1tQTM6AwjbR+FqAWwDl3xx
    QdFSKCNCb83tAi/Wl6qXQcMiphxaRCn8Y+j0yQsDZlZ7SPyeVAI9OSZ+9FS8eXczjev5
    1xkwa2hJgYmX9riiLpjaX7MABxgY4bD5XPj9cjEXI3l4hpzzrTgUbfC9X0D2b95WyzXY
    NgEQ==
    ARC-Authentication-Results: i=1; mx.google.com;
    spf=neutral (google.com: 72.43.74.25 is neither permitted nor denied by best guess record for domain of asterisk@phones.microworx.com) smtp.mailfrom=asterisk@phones.microworx.com;
    dmarc=fail (p=NONE sp=NONE dis=NONE) header.from=microworx.com
    Return-Path: <asterisk@phones.microworx.com>
    Received: from EXCHANGE2K16.office.microworx.com ([72.43.74.25])
    by mx.google.com with ESMTPS id f14si2059398ila.81.2021.11.17.12.17.58
    for <<WITHHELD>@Stuff .com>
    (version=TLS1_2 cipher=ECDHE-ECDSA-AES128-GCM-SHA256 bits=128/128);
    Wed, 17 Nov 2021 12:17:58 -0800 (PST)
    Received-SPF: neutral (google.com: 72.43.74.25 is neither permitted nor denied by best guess record for domain of asterisk@phones.microworx.com) client-ip=72.43.74.25;
    Authentication-Results: mx.google.com;
    spf=neutral (google.com: 72.43.74.25 is neither permitted nor denied by best guess record for domain of asterisk@phones.microworx.com) smtp.mailfrom=asterisk@phones.microworx.com;
    dmarc=fail (p=NONE sp=NONE dis=NONE) header.from=microworx.com
    Received: from EXCHANGE2K16.office.microworx.com (192.168.0.4) by EXCHANGE2k16.office.microworx.com (192.168.0.4) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_128_GCM_SHA256) id 15.1.2308.15; Wed, 17 Nov 2021 15:17:22 -0500
    Received: from MWX-Phones (192.168.0.9) by EXCHANGE2K16.office.microworx.com (192.168.0.4) with Microsoft SMTP Server id 15.1.2308.15 via Frontend Transport; Wed, 17 Nov 2021 15:17:22 -0500
    Received: by MWX-Phones (Postfix, from userid 995) id 2F0FB813665D; Wed, 17 Nov 2021 15:17:57 -0500 (EST)
    Date: Wed, 17 Nov 2021 15:17:57 -0500
    From: FreePBX Phone System <rob@microworx.com>
    To: Emergency Voicemail <techoncall@microworx.com>
    Subject: FreePBX Voicemail Notification
    Message-ID: <Asterisk-7-1490993192-500-2677@VOIP01.OFFICE.microworx.com>
    X-Asterisk-CallerID: 105
    X-Asterisk-CallerIDName: 105-Kevin
    MIME-Version: 1.0
    Content-Type: multipart/mixed; boundary="----voicemail_750026771517083761"
    Return-Path: asterisk@phones.microworx.com
    X-Auto-Response-Suppress: DR, OOF, AutoReply

    ------voicemail_750026771517083761
    Content-Type: text/plain; charset="UTF-8"
    Content-Transfer-Encoding: 8bit

    Emergency Voicemail,

    There is a new voicemail in mailbox 500:

    From:   "105-Kevin" <105>  
    Length: 0:07 seconds  
    Date:   Wednesday, November 17, 2021 at 03:17:57 PM  
    

    Dial *98 to access your voicemail by phone.
    Visit http://AMPWEBADDRESS/ucp to check your voicemail with a web browser.

    ------voicemail_750026771517083761
    Content-Type: audio/x-wav; name="msg0006.wav"
    Content-Transfer-Encoding: base64
    Content-Description: Voicemail sound attachment.
    Content-Disposition: attachment; filename="msg0006.wav"

    ------voicemail_750026771517083761--

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  3. Andy David - MVP 142.2K Reputation points MVP
    2021-11-17T20:44:03.627+00:00

    here is your issue as suspected

    spf=neutral (google.com: 72.43.74.25 is neither permitted nor denied by best guess record for domain of asterisk@phones.microworx.com) smtp.mailfrom=asterisk@phones.microworx.com;
    dmarc=fail (p=NONE sp=NONE dis=NONE) header.from=microworx.com

    The FROM domain doesnt have am SPF record:
    phones.microworx.com

    Verizon is probably dropping those based on that.

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