Duplicate emails in Office365 sent folder when sent via iOS SMTP

%3CLINGO-SUB%20id%3D%22lingo-sub-378139%22%20slang%3D%22en-US%22%3EDuplicate%20emails%20in%20Office365%20sent%20folder%20when%20sent%20via%20iOS%20SMTP%3C%2FLINGO-SUB%3E%3CLINGO-BODY%20id%3D%22lingo-body-378139%22%20slang%3D%22en-US%22%3E%3CP%3EHaving%20a%20weird%20issue%20that%20just%20popped%20about%20about%207%20days%20ago.%20Prior%20to%20that%20never%20noticed%20this%20issue%20which%20leads%20me%20to%20believe%20something%20changed%20with%20the%20way%20Office365%20does%20SMTP%20submission.%20This%20relates%20to%20the%20way%20iOS%20and%20Office365%20work%20together%20when%20using%20IMAP%2FSMTP%20configuration.%20We%20do%20not%20want%20to%20use%20the%20Outlook%20for%20iOS%20app%2C%20rather%20we%20want%20to%20use%20IMAP%20and%20SMTP.%20On%20the%20iOS%20device%2C%20the%20device%20shows%20the%20sent%20items%20folder%20and%20one%20entry.%20However%2C%20when%20reviewing%20in%20the%20Outlook%20client%20or%20office365%20web%20client%2C%20can%20see%20multiple%20entries%20for%20same%20email%20message%2C%20only%20difference%20being%20the%20size%20of%20the%20message.%20Note%20the%20message%20IDs%20on%20both%20messages%20are%20the%20same%20so%20I%20assume%20that%20is%20how%20iOS%20knows%20to%20only%20show%20the%20message%20once.%20Confused%20as%20to%20why%20the%20Outlook%20email%20client%20shows%20it%20multiple%20times%20(see%20screenshot).%3C%2FP%3E%3CP%3E%26nbsp%3B%3C%2FP%3E%3CP%3EIf%20I%20turn%20off%20the%20iOS%20option%20to%20force%20it%20to%20save%20messages%20only%20on%20the%20device%20after%20sending%2C%20then%20I%20cannot%20view%20the%20entire%20Sent%20items%20folder%20for%20this%20IMAP%20account.%20So%20that%20option%20is%20out.%3C%2FP%3E%3CP%3E%26nbsp%3B%3C%2FP%3E%3CP%3ESample%20header%20from%20email%201%20Received%3A%20from%20%5BIPv6%3A2600%3A1011%3Ab10d%3A23f4%3Ab9e3%3A6afc%3Abb67%3Abcaf%5D%20(2603%3A10b6%3Aa03%3A114%3A%3A11)%20by%20BYAPR18MB2966.namprd18.prod.outlook.com%20(2603%3A10b6%3Aa03%3A111%3A%3A18)%20with%20Microsoft%20SMTP%20Server%20(version%3DTLS1_2%2C%20cipher%3DTLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384)%20id%2015.20.1730.15%20via%20Mailbox%20Transport%3B%20Thu%2C%2021%20Mar%202019%2006%3A41%3A49%20%2B0000%20From%3A%20name%20goes%20here%20%3CEMAILADDRESSGOESHERE%3E%20Content-Type%3A%20text%2Fplain%3B%20charset%3Dus-ascii%20Content-Transfer-Encoding%3A%20quoted-printable%20Mime-Version%3A%201.0%20(1.0)%20Date%3A%20Wed%2C%2020%20Mar%202019%2023%3A41%3A48%20-0700%20Subject%3A%20Re%3A%20test2%20Message-Id%3A%20%26lt%3B%3CSTRONG%3EDF64BCAE-6B3E-4109-A320-FEF7A4AB626B%3C%2FSTRONG%3E%40domaingoeshere.com%26gt%3B%20References%3A%20%3CE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%20In-Reply-To%3A%20%3CE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%20To%3A%20EMAILADDRESSGOESHERE*REDACTED%40gmail.com%20X-Mailer%3A%20iPhone%20Mail%20(16D57)%20X-MS-Exchange-Organization-ExpirationStartTime%3A%2021%20Mar%202019%2006%3A41%3A49.5534%20(UTC)%20X-MS-Exchange-Organization-ExpirationStartTimeReason%3A%20OriginalSubmit%20X-MS-Exchange-Organization-ExpirationInterval%3A%202%3A00%3A00%3A00.0000000%20X-MS-Exchange-Organization-ExpirationIntervalReason%3A%20OriginalSubmit%20X-MS-Exchange-Organization-Network-Message-Id%3A%20a14e7dcc-4688-4c11-67dd-08d6adc84bc1%20X-MS-Exchange-Organization-AuthSource%3A%20BYAPR18MB2966.namprd18.prod.outlook.com%20X-MS-Exchange-Organization-AuthAs%3A%20Internal%20X-MS-Exchange-Organization-AuthMechanism%3A%2006%20X-Originating-IP%3A%20%5B2600%3A1011%3Ab10d%3A23f4%3Ab9e3%3A6afc%3Abb67%3Abcaf%5D%20X-ClientProxiedBy%3A%20BYAPR21CA0001.namprd21.prod.outlook.com%20(2603%3A10b6%3Aa03%3A114%3A%3A11)%20To%20BYAPR18MB2966.namprd18.prod.outlook.com%20(2603%3A10b6%3Aa03%3A111%3A%3A18)%20X-MS-Exchange-Organization-MessageDirectionality%3A%20Originating%20Return-Path%3A%20EMAILADDRESSGOESHERE*REDACTED%40domaingoeshere.com%3C%2FE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%3C%2FE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%3C%2FEMAILADDRESSGOESHERE%3E%3C%2FP%3E%3CP%3E%26nbsp%3B%3C%2FP%3E%3CP%3ESample%20header%20from%20email%202%20(duplicate%20of%20email%201)%20Content-Type%3A%20text%2Fplain%3B%20charset%3Dus-ascii%20Content-Transfer-Encoding%3A%20quoted-printable%20From%3A%20name%20goes%20here%20%3CEMAILADDRESSGOESHERE%3E%20Mime-Version%3A%201.0%20(1.0)%20Date%3A%20Wed%2C%2020%20Mar%202019%2023%3A41%3A48%20-0700%20Subject%3A%20Re%3A%20test2%20Message-Id%3A%20%26lt%3B%3CSTRONG%3EDF64BCAE-6B3E-4109-A320-FEF7A4AB626B%3C%2FSTRONG%3E%40domaingoeshere.com%26gt%3B%20References%3A%20%3CE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%20In-Reply-To%3A%20%3CE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%20To%3A%20EMAILADDRESSGOESHERE*REDACTED%40gmail.com%3C%2FE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%3C%2FE6FD961C-C2C2-4613-B1FD-FCAE58040BF9%3E%3C%2FEMAILADDRESSGOESHERE%3E%3C%2FP%3E%3C%2FLINGO-BODY%3E%3CLINGO-LABS%20id%3D%22lingo-labs-378139%22%20slang%3D%22en-US%22%3E%3CLINGO-LABEL%3EExchange%3C%2FLINGO-LABEL%3E%3CLINGO-LABEL%3EOffice%20365%3C%2FLINGO-LABEL%3E%3C%2FLINGO-LABS%3E
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New Contributor

Having a weird issue that just popped about about 7 days ago. Prior to that never noticed this issue which leads me to believe something changed with the way Office365 does SMTP submission. This relates to the way iOS and Office365 work together when using IMAP/SMTP configuration. We do not want to use the Outlook for iOS app, rather we want to use IMAP and SMTP. On the iOS device, the device shows the sent items folder and one entry. However, when reviewing in the Outlook client or office365 web client, can see multiple entries for same email message, only difference being the size of the message. Note the message IDs on both messages are the same so I assume that is how iOS knows to only show the message once. Confused as to why the Outlook email client shows it multiple times (see screenshot).

 

If I turn off the iOS option to force it to save messages only on the device after sending, then I cannot view the entire Sent items folder for this IMAP account. So that option is out.

 

Sample header from email 1 Received: from [IPv6:2600:1011:b10d:23f4:b9e3:6afc:bb67:bcaf] (2603:10b6:a03:114::11) by BYAPR18MB2966.namprd18.prod.outlook.com (2603:10b6:a03:111::18) with Microsoft SMTP Server (version=TLS1_2, cipher=TLS_ECDHE_RSA_WITH_AES_256_GCM_SHA384) id 15.20.1730.15 via Mailbox Transport; Thu, 21 Mar 2019 06:41:49 +0000 From: name goes here <EMAILADDRESSGOESHERE*REDACTED@domaingoeshere.com> Content-Type: text/plain; charset=us-ascii Content-Transfer-Encoding: quoted-printable Mime-Version: 1.0 (1.0) Date: Wed, 20 Mar 2019 23:41:48 -0700 Subject: Re: test2 Message-Id: <DF64BCAE-6B3E-4109-A320-FEF7A4AB626B@domaingoeshere.com> References: <E6FD961C-C2C2-4613-B1FD-FCAE58040BF9@domaingoeshere.com> In-Reply-To: <E6FD961C-C2C2-4613-B1FD-FCAE58040BF9@domaingoeshere.com> To: EMAILADDRESSGOESHERE*REDACTED@gmail.com X-Mailer: iPhone Mail (16D57) X-MS-Exchange-Organization-ExpirationStartTime: 21 Mar 2019 06:41:49.5534 (UTC) X-MS-Exchange-Organization-ExpirationStartTimeReason: OriginalSubmit X-MS-Exchange-Organization-ExpirationInterval: 2:00:00:00.0000000 X-MS-Exchange-Organization-ExpirationIntervalReason: OriginalSubmit X-MS-Exchange-Organization-Network-Message-Id: a14e7dcc-4688-4c11-67dd-08d6adc84bc1 X-MS-Exchange-Organization-AuthSource: BYAPR18MB2966.namprd18.prod.outlook.com X-MS-Exchange-Organization-AuthAs: Internal X-MS-Exchange-Organization-AuthMechanism: 06 X-Originating-IP: [2600:1011:b10d:23f4:b9e3:6afc:bb67:bcaf] X-ClientProxiedBy: BYAPR21CA0001.namprd21.prod.outlook.com (2603:10b6:a03:114::11) To BYAPR18MB2966.namprd18.prod.outlook.com (2603:10b6:a03:111::18) X-MS-Exchange-Organization-MessageDirectionality: Originating Return-Path: EMAILADDRESSGOESHERE*REDACTED@domaingoeshere.com

 

Sample header from email 2 (duplicate of email 1) Content-Type: text/plain; charset=us-ascii Content-Transfer-Encoding: quoted-printable From: name goes here <EMAILADDRESSGOESHERE*REDACTED@domaingoeshere.com> Mime-Version: 1.0 (1.0) Date: Wed, 20 Mar 2019 23:41:48 -0700 Subject: Re: test2 Message-Id: <DF64BCAE-6B3E-4109-A320-FEF7A4AB626B@domaingoeshere.com> References: <E6FD961C-C2C2-4613-B1FD-FCAE58040BF9@domaingoeshere.com> In-Reply-To: <E6FD961C-C2C2-4613-B1FD-FCAE58040BF9@domaingoeshere.com> To: EMAILADDRESSGOESHERE*REDACTED@gmail.com

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