Apple Mail emails using exchange server are received by Outlook app users as blank email with body in attachment

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Apple Mail emails using exchange server are received by Outlook app users as blank email with body in attachment

I've been notified by colleagues at a variety of institutions who all use the Outlook app to access their email that mine (from my Outlook exchange account) show up as a blank email with my text in an attachment. Users in my institution receive them fine, and when I receive replies everything looks normal to me. I don't have a problem when I send from my Google accounts using Apple Mail, so the problem is limited to using Apple Mail to send from my Outlook exchange account to other Outlook app users. I see others in the community have had this issue too, but I didn't see any resolutions. This has happened with multiple versions of OS X and with and without the Mailbutler plug-in installed.

Screenshot included below shows how these recipients see my emails

Posted on Mar 22, 2023 9:05 AM

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Answer 1

carolt82 Author

Level 1

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Mar 22, 2023 9:44 AM in response to carolt82

Upon further testing, the issue happens when the email is signed or not.

Examples of emailing from my Outlook exchange account using Apple Mail and using the Outlook app. Both viewed in the Outlook app.

It appears that is issue is how Mail is sending emails differently from Outlook and the receiving exchange server wraps an external sender warning. Messages sent from Outlook are wrapped appropriately and those sent from Mail are converted into an attachment with the warning wrapper in the new body of the email.

Sent with Apple Mail

Sent with Outlook

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Apple Mail emails using exchange server are received by Outlook app users as blank email with body in attachment

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