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Messages with inline attachments are received as multiple attachments in Exchange Server

Symptoms
In a Microsoft Exchange Server environment, a user sends an email message that has one or more inline attachments. When the recipient receives the message, it does not contain any inline attachments. Instead the message contains one or more attachments. These attachments may include text files that contain text content from the original body of the message.
More information
If the recipient or sender is external to the Exchange organization, you can enable pipeline tracing to view a snapshot of the message as it's received by Exchange. Analysis of the message shows the correct boundary being used within separate parts of the message. However, the section that contains the message text uses the Content-Type of text/plain. Exchange uses this value to determine the format of the message and in this scenario uses the Plain Text format, which cannot display inline images. Therefore, each section is added as a separate attachment to the message.

The following is a sample message:

Content-Type: multipart/mixed; boundary="_005_D8FB5BDDF996406AB2DC5D568B915E90contosocom_"MIME-Version: 1.0X-MS-Exchange-Organization-ContentConversionOptions: False;00160000;True;;iso-8859-1--_005_D8FB5BDDF996406AB2DC5D568B915E90contosocom_Content-Type: text/plain; charset="us-ascii"Content-ID: <410CE56D5777AA47AD1FE9D67F555E14@contoso.com>Content-Transfer-Encoding: quoted-printableText first--_005_D8FB5BDDF996406AB2DC5D568B915E90contosocom_Content-Type: image/png; name="image1.PNG"Content-Description: image1.PNGContent-Disposition: attachment; filename="image1.PNG"; size=75040; creation-date="Wed, 30 Dec 2015 14:02:31 GMT"; modification-date="Wed, 30 Dec 2015 14:02:31 GMT"Content-ID: <0BE526FEDDDBFA4696A137EE7FAB0129@contoso.com>Content-Transfer-Encoding: base64/9j/4AAQSkZJRgABAQAASABIAAD/4QCKRXhpZgAATU0AKgAAAAgAAYdpAAQAAAABAAAAGgAAAAAABZADAAIAAAAUAAAAXJKGAAcAAAASAAAAcKABAAMAAAABAAEAAKACAAQAAAABAAAEAKADAAQAAAAB

Properties

Article ID: 3108205 - Last Review: 01/22/2016 21:08:00 - Revision: 4.0

Exchange Server 2016 Enterprise Edition, Exchange Server 2016 Standard Edition, Microsoft Exchange Server 2013 Enterprise, Microsoft Exchange Server 2013 Standard, Microsoft Exchange Server 2010 Standard, Microsoft Exchange Server 2007 Enterprise Edition, Microsoft Exchange Server 2007 Standard Edition, Microsoft Exchange Online

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