CF10 office 365 email settings result in undelivered mail

Hello, can someone help me with the Cold Fusion admin settings to allow mail to be sent using Office 365?
Thanks,
Renee

Hello,
Yes, there are entries in the log file.  I sent them to you.  Do you need the mail file again?
This is the error:
"Error","scheduler-4","10/08/14","11:00:33",,"javax.mail.MessagingException: Could not connect to SMTP host: smtp.office365.com, port: 587;   nested exception is:      javax.net.ssl.SSLException: Unrecognized SSL message, plaintext connection?"
Thanks,
Renee

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    The ONLY mail that was recorded in the message Trace in Office 365 was emails we had sent from On-prem to other office 365 accounts (For example btconnect.com, and some of our clients whom also use office 365) .
    How is office 365 picking up mail we've sent from our On-Prem server? Is there integration out of the box in exchange 2013 which auto interfaces with office 365? What on earth has happened here?
    I'm really confused.
    -------- For troubleshooting purposes...
    Headers in the email which arrived in my personal office 365 account from the ON-PREM SERVER
    Received: from AMSPR05MB065.eurprd05.prod.outlook.com (10.242.89.142) by
    DBXPR05MB079.eurprd05.prod.outlook.com (10.242.138.22) with Microsoft SMTP
    Server (TLS) id 15.1.93.16 via Mailbox Transport; Thu, 5 Mar 2015 16:16:31
    +0000
    Received: from DBXPR05CA0014.eurprd05.prod.outlook.com (10.255.178.14) by
    AMSPR05MB065.eurprd05.prod.outlook.com (10.242.89.142) with Microsoft SMTP
    Server (TLS) id 15.1.99.14; Thu, 5 Mar 2015 16:16:30 +0000
    Received: from DB3FFO11FD028.protection.gbl (2a01:111:f400:7e04::145) by
    DBXPR05CA0014.outlook.office365.com (2a01:111:e400:9434::14) with Microsoft
    SMTP Server (TLS) id 15.1.106.15 via Frontend Transport; Thu, 5 Mar 2015
    16:16:29 +0000
    Received: from emea01-am1-obe.outbound.protection.outlook.com (157.56.112.128)
    by DB3FFO11FD028.mail.protection.outlook.com (10.47.217.59) with Microsoft
    SMTP Server (TLS) id 15.1.99.6 via Frontend Transport; Thu, 5 Mar 2015
    16:16:28 +0000
    Received: from DB4PR04CA0010.eurprd04.prod.outlook.com (25.160.41.20) by
    DB3PR04MB236.eurprd04.prod.outlook.com (10.242.130.24) with Microsoft SMTP
    Server (TLS) id 15.1.99.14; Thu, 5 Mar 2015 16:16:26 +0000
    Received: from DB3FFO11FD040.protection.gbl (2a01:111:f400:7e04::184) by
    DB4PR04CA0010.outlook.office365.com (2a01:111:e400:9852::20) with Microsoft
    SMTP Server (TLS) id 15.1.106.15 via Frontend Transport; Thu, 5 Mar 2015
    16:16:26 +0000
    Received: from mail.localdomainhere (<IP OF OUR ON-PREM SERVER GOES HERE>) by
    DB3FFO11FD040.mail.protection.outlook.com (10.47.217.71) with Microsoft SMTP
    Server (TLS) id 15.1.99.6 via Frontend Transport; Thu, 5 Mar 2015 16:16:25
    +0000
    Received: from INT-EX-01.localdomainhere (192.168.142.20) by
    INT-EX-01.localdomainhere (192.168.142.20) with Microsoft SMTP Server (TLS) id
    15.0.913.22; Thu, 5 Mar 2015 16:15:55 +0000
    Received: from INT-EX-01.localdomainhere ([fe80::aca4:88cf:3eaf:57dc]) by
    INT-EX-01.localdomainhere ([fe80::aca4:88cf:3eaf:57dc%12]) with mapi id
    15.00.0913.011; Thu, 5 Mar 2015 16:15:55 +0000
    From: Jake Ives <[email protected]>
    To: Jake Ives <[email protected]>
    Subject: Test01
    Thread-Topic: Test01
    Thread-Index: AdBXX6dyI5u99OGoSKmXroKKyMA3Tg==
    Date: Thu, 5 Mar 2015 16:15:54 +0000
    Message-ID: <[email protected]>
    Accept-Language: en-US, en-GB
    Content-Language: en-US
    X-MS-Has-Attach: yes
    X-MS-TNEF-Correlator:
    x-originating-ip: [192.168.142.73]
    Content-Type: multipart/related;
                boundary="_004_081f834d85b7436193fa887613b9dac7INTEX01localdomainhere_";
                type="multipart/alternative"
    MIME-Version: 1.0
    Return-Path:
    [email protected]
    X-EOPAttributedMessage: 1
    Received-SPF: Pass (protection.outlook.com: domain of domain.com
    designates <IP OF ONPREM SERVER HERE> as permitted sender)
    receiver=protection.outlook.com; client-ip=<IP OF OUR ON-PREM SERVER GOES HERE;
    helo=mail.domain.co.uk;
    Authentication-Results: spf=pass (sender IP is <IP OF OUR ON-PREM SERVER GOES HERE>)
    [email protected]; ives.gb.net; dkim=none (message not
    signed) header.d=none;ives.gb.net; dkim=none (message not signed)
    header.d=none;ives.gb.net; dmarc=none action=none header.from=domain.com;
    X-Forefront-Antispam-Report-Untrusted: CIP:<IP OF ON PREM SERVER HERE>;CTRY:GB;IPV:NLI;EFV:NLI;BMV:0;SFV:NSPM;SFS:(10019020)(438002)(189002)(199003)(71364002)(87936001)(2656002)(98436002)(92726002)(102836002)(108616004)(19625215002)(19618635001)(512954002)(92566002)(229853001)(107886001)(66926002)(18206015028)(84326002)(16796002)(19300405004)(450100001)(19580395003)(2900100001)(77156002)(15974865002)(62966003)(5250100002)(5310100001)(99936001)(15395725005)(16236675004)(110136001)(17760045003)(67866002)(86362001)(19617315012)(19627595001)(15975445007)(19580405001)(54356999)(22756005)(50986999)(6806004)(46102003)(74482002)(106466001)(33646002)(7099025)(24736002)(15669805003);DIR:OUT;SFP:1102;SCL:1;SRVR:DB3PR04MB236;H:mail.domain.co.uk;FPR:;SPF:Pass;MLV:ovrnspm;MX:1;A:1;PTR:mail.domain.co.uk;LANG:en;
    X-Microsoft-Antispam: UriScan:;BCL:0;PCL:0;RULEID:;SRVR:DB3PR04MB236;UriScan:;BCL:0;PCL:0;RULEID:;SRVR:AMSPR05MB065;
    X-Microsoft-Antispam-PRVS: <[email protected]outlook.com>
    X-Exchange-Antispam-Report-Test: UriScan:;UriScan:;
    X-Exchange-Antispam-Report-CFA-Test: BCL:0;PCL:0;RULEID:(601004)(5001007)(5005006);SRVR:DB3PR04MB236;BCL:0;PCL:0;RULEID:;SRVR:DB3PR04MB236;BCL:0;PCL:0;RULEID:(601004);SRVR:AMSPR05MB065;BCL:0;PCL:0;RULEID:;SRVR:AMSPR05MB065;
    X-Forefront-PRVS: 05066DEDBB
    X-MS-Exchange-Transport-CrossTenantHeadersStamped: DB3PR04MB236
    X-MS-Exchange-Organization-MessageDirectionality: Incoming
    Received-SPF: Fail (protection.outlook.com: domain of domain.com does not
    designate 157.56.112.128 as permitted sender)
    receiver=protection.outlook.com; client-ip=157.56.112.128;
    helo=emea01-am1-obe.outbound.protection.outlook.com;
    Authentication-Results: spf=fail (sender IP is 157.56.112.128)
    [email protected];
    X-Forefront-Antispam-Report: CIP:157.56.112.128;CTRY:US;IPV:NLI;IPV:NLI;EFV:NLI;SFV:NSPM;SFS:(339900001)(489007)(189002)(71364002)(199003)(102836002)(92726002)(15975445007)(92566002)(17760045003)(62966003)(106466001)(15395725005)(16236675004)(77156002)(110136001)(107886001)(450100001)(5310100001)(229853001)(22756005)(98436002)(2900100001)(5250100002)(19625215002)(66926002)(99936001)(33646002)(15974865002)(19617315012)(19627595001)(67866002)(54356999)(108616004)(19300405004)(19618635001)(87836001)(2656002)(18206015028)(85426001)(512954002)(86362001)(6806004)(46102003)(74482002)(84326002)(19580395003)(50986999)(19580405001)(7099025)(24736002)(15669805003);DIR:INB;SFP:;SCL:1;SRVR:AMSPR05MB065;H:emea01-am1-obe.outbound.protection.outlook.com;FPR:;SPF:Fail;MLV:ovrnspm;MX:1;A:1;PTR:mail-am1on0128.outbound.protection.outlook.com;LANG:en;
    X-MS-Exchange-Transport-CrossTenantHeadersStripped: DB3FFO11FD028.protection.gbl
    X-MS-Exchange-Transport-CrossTenantHeadersPromoted: DB3FFO11FD028.protection.gbl
    X-MS-Exchange-Organization-Network-Message-Id: 927151e3-02c4-4c46-5539-08d22576df82
    X-MS-Exchange-Organization-AVStamp-Service: 1.0
    X-MS-Exchange-Organization-SCL: 1
    X-MS-Exchange-CrossTenant-OriginalArrivalTime: 05 Mar 2015 16:16:28.9728
    (UTC)
    X-MS-Exchange-CrossTenant-Id: cd52bfe2-da2e-446d-b8f1-e78db861d489
    X-MS-Exchange-CrossTenant-OriginalAttributedTenantConnectingIp: TenantId=bfa61dad-1543-4f3b-8075-03498e9f4fcb;Ip=[IP OF ON PREM SERVER HERE]
    X-MS-Exchange-CrossTenant-FromEntityHeader: Internet
    X-MS-Exchange-Transport-CrossTenantHeadersStamped: AMSPR05MB065
    X-MS-Exchange-Organization-AuthSource: DB3FFO11FD028.protection.gbl
    X-MS-Exchange-Organization-AuthAs: Anonymous
    X-MS-Exchange-Transport-EndToEndLatency: 00:00:03.5565465

    MX records are not set to office 365, the MX is pointing directly to the on-prem exchange server. 
    The problem is; Office 365 Mail Delivery Trace is displaying mail we've sent via our On-Prem server - We are having trouble understanding why this is happening.
    To clarify, the message tracer in Office 365 is displaying outbound mail (Which for example, a user has sent out from their outlook) BUT only outbound mail which is being sent to other office 365 users.
    We do not have mail on office 365, only on-premise hence the reason why we are flabbergasted to why the mail we are sending out would be displaying on the office 365 message tracer.
    To further clarify, we are only seeing addresses in the office 365 message trace which belong to recipients whom use office 365 for their mail.
    Hope this makes sense.
    getting messy O365 users to another O365 you mean?
    You mentioned if they send email using their MS Outlook Client.
    I'd suggest you to send another email to the same recipient but using OWA
    There may have been an office 365 connector in Outlook.
    Where Technology Meets Talent

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