Outlook for MAC does not include attached files

Copper Contributor

I experience that Outlook very often doesn't send the files I have attached. Everything looks correct until the mail I sent. Then it's like the attachment is removed from the e-mail. Also, my image in the signature is often missing. How can I solve this issue? 

54 Replies


If you're facing issues with Outlook for Mac not including attached files and missing images in the signature, here are some troubleshooting steps you can try:

  1. Check attachment size: Ensure that the size of the attached files does not exceed the maximum allowed attachment size set by your email provider. Large attachments may be stripped from the email during the sending process.
  2. Avoid special characters or long file names: Simplify the names of the attached files by removing any special characters or long file names. Sometimes, certain characters or long names can cause issues with attachments.
  3. Use a different email format: Try changing the email format from HTML to Plain Text or Rich Text to see if it resolves the issue. Sometimes, compatibility issues between different email formats can affect the attachment functionality.
  4. Update Outlook: Check for any available updates for Outlook for Mac and install them. Updates often include bug fixes and improvements that can resolve attachment-related issues.
  5. Disable add-ins: Temporarily disable any add-ins or plugins in Outlook for Mac to check if they are causing the problem. Add-ins can sometimes interfere with the attachment functionality.
  6. Repair Outlook profile: Use the Microsoft Database Utility to repair your Outlook profile. This utility can help fix issues with the Outlook database, which may be impacting the attachment and signature functionality.
  7. Rebuild the Outlook database: If repairing the profile doesn't solve the issue, you can try rebuilding the Outlook database. This process can help fix any corruption in the database that might be causing the problem. To do this, quit Outlook, navigate to the "Documents/Microsoft User Data/Office 2011 Identities" folder, and rename the folder to create a new Outlook database.
  8. Reinstall Outlook: If all else fails, consider uninstalling and reinstalling Outlook for Mac. This can provide a clean installation and may resolve any persistent issues.
we are also getting this and the work around was to revert to legacy.

any updates

@Suleyman Ali 


I have the same issue and I have found something which might help you.

- If you add attachment and then start writing email, the attachment is never sent. It disappears.

- If you write email and at the very end add attachment and click on send button, it always send the attachment.


@Suleyman Ali 


How to Fix Attachments Not Showing in Outlook for Mac


My answers are voluntary and without guarantee!


Hope this will help you.



i am going to see if I can reproduce this and then see if Microsoft know anything about this bug


thank you

this is now with Micorosft office 365 tech det under ID EX637339. A potential fix will be out in August
What do we do between now and then?!
not much you can do until a fix is sorted. Options are

1. use outlook on the web only (we have not asked our users to do that)
2. revert to legacy outlook
3. add the attachments at the end of composing the message

@Suleyman Ali Any word on this fix? Been dealing with this with multiple users. 

Do you have any update on this specific issue?

@Casperms, this is an active incident EX637339. The latest is "Current status: We're continuing to develop an Outlook for Mac update that will correct this issue, that we still expect it will be available for download in mid-August. We anticipate providing a release date by our next communication update."

You are actually right so far it works - thank you sir! @NikolinoDE 

pk, their current stgatus:


"Current status: Microsoft completed the Outlook for Mac update which contains the fix and released it to the affected environments. The majority of affected users should have automatically received the fix at this point. However, we've determined that the existing fix may not address all factors contributing to the issue. Microsoft are developing and testing an additional mitigation to address any remaining impact, which we anticipate will begin deploying to affected users by our next scheduled update."


so fix is being deployed

Although this is just about attachments. users have also been sending issues where embedded images (signatures) are also being stripped. Lets hope the fix will work soon

@Suleyman Ali 


Im afraid the problem remains for me after updating today. Both attachments and images in my signature is removed a few seconds after I've sent an email.



Same for me. I have updated to Outlook 16.76 (recent release) and images in my signature are stripped as well as attachments. This is extremely frustrating!

@bsm007Indeed. I'm on the same build/version. Before that I reinstalled Outlook from scratch on a brand new and clean Mac, but the problems persists. Its random when attachments are deleted, so pretty hard to error-track. Its more often then not now unfortunately.


Very annoying having customers and partners complain and ask for attachments. I'm trying to work around through my private gmail and Outlook online (which works), but this is really unbearable.  

Hey everybody.  I fix stated above is to wait until the very very end and attach the files, then press send.  Don't add anyone to the email address or make any modifications to the email and it works.   It's annoying, as you have to download and upload at the end even when forwarding emails!!! :facepalm: @Steffen_Uniwise 

@MCADK I have the same issue, very annoying.