Mailing from Apple Mail to Windows Outlook doesn't show attachments

Tech Support
1

Problem:
Sending an email with attachment, from Apple Mail to Office 365; The attachment is not shown, in fact, there is no trace of any attachment at all. Forwarding that mail to me shows the attachment again!?

Sender is using Office 365 with Apple Mail app. Reciever is Windows.

I have tried to dissect a working email vs a non working email to no avail.

Somehow Office 365 refuse to understand that there’s an attachment, even though it’s still attached when forwarding.

Any ideas where I should start to look? :thinking:

2

Try sending using webmail to see if that makes any difference. If the attachment is visible to the receiver this time, the problem could be Apple Mail.

If attachment still doesn’t show have recipient look at the message in webmail. What email client is recipient using? If receiver can see attachment in webmail the problem may be his client.

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In case you are not aware of the issues involved:

  • To send Windows-friendly attachments for all messages, choose Edit > Attachments, then select Always Send Windows-Friendly Attachments.
  • To send Windows-friendly attachments for a single message, click the Attachment button in the toolbar of the new message window, then select Send Windows-Friendly Attachments (if the checkbox isn’t shown, click Show Details).
4

Is the receiver also using Office 365?

It happens to me when I send from my staff account (Office 365) to a student/faculty account (Gmail). If I send a mail to a staff account, the attachments always work. Therefore, I use Dropbox for attachment links when sending to non-O365 accounts. It happens in both Outlook and Apple Mail, so it’s server-related, not software—I think.

I would love to find an easy fix for this, too, but I’ve been unable to.

5

I know this may sound stupid, and it probably is. But I’ve experienced a few of my colleagues who use Outlook not know where to look for attachments in the UI.

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Followup:

  • I installed Outlook on his Mac, and looked at the email in the Sent box. No attachments there either… Ie, the attachments exists in Mail, but not in Outlook. Weird.
  • I thought that the Windows-friendly attachments option was removed in Sonoma, but I see now that it still exists. Will definitely look at that!
  • @rms - Not stupid, that was the first thing I looked at, because I was convinced that was the problem – “SBK” (Shit Behind the Keyboard). But nope, not a hint about any attachments…

Thanks for the input, I’ll be back with a report.

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7

If the file is large, MacOS may be using the icloud Transfer feature, but Outlook may not recognise that and/or Outlook (or a security tool installed on the PC) may be hading access to the link to “protect” the worker against phishing.

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