Image attachements sent to microsoft exchange email addresses do not come through

Exchange is probably the worst email server with respect to actual email. It was designed for only handling internal emails generated on its own system, then "internet email," as they term it, was cobbled onto it.

Outlook has a very poor performance when handling non-exchange email. Outlook on Windows even has difficulty with emails generated on Outlook for Mac.

Apple Mail generates internet standard compliant emails. Outlook just doesn't display them properly.

Exchange servers can be configured to delete or hide attachments that could possibly compromise the network (on a Windows network that is just about any file at all). Apple Mail "tags" attachments with the completely standards compliant "inline" directive. It may be that those servers are configured to block (delete) any inline attachment.

Hello tykockin,

Thank you for posting in the Apple Support Communities. I understand you've been running into issues sending attachments in Mail.

You've done some good testing to help narrow things down. To clarify, is this happening with a specific recipient, or all recipients that use Outlook? Also, it sounds like you're able to send attachments from Mail to other types of accounts, like Gmail; is that right?

Which macOS version are you using? You can check by clicking Apple menu () > About This Mac. If you're not running the latest macOS version, you might consider updating: Back up your Mac with Time Machine and How to update the software on your Mac.

You might also test this in a temporary administrator account on your Mac. Creating a new user and testing there will tell you more about the issue, and helps determine if it's system-wide or user account-specific. There are other factors to consider with an issue like this, but the test user would help narrow things down on the Mac end: How to test an issue in another user account on your Mac.

Hopefully the information above helps you.

Kind regards.

Hi

that is an interesting problem.

I did the test with what I have and I used my Gmail and send attachment.jpg to my Outlook, and arrived back on my Mac as image in the Outlook account on my mac mail.

To clarify, my Outlook is just online outlook account at https://outlook.live.com/mail/, and I have it also in my Mac mail.

Does this help or did I miss it.

At least it looks like the mac mail is working.

my work-around has been to send everything as PDF. I just got fed up and posted here finally.

You can also Zip the images. It doesn't do anything to compress them, but it does "package" them into a file that seems to be handled ok by Outlook.

Thank you, but I do not plan to do that.

It is clear to me that the Exchange Server is blocking anything but PDF attachments.