My outlook for Mac fails to send attachments, the paperclip icon disappears a few seconds after sending the email and the attachment disappears. I have cleared the cache but it hasn't resolved it. My 365 apps are up to date and I am running Ventura 13.4.1 Anyone got any ideas?

ActionPlus I'm also suffering from this and have had to move our entire team to webmail until this is resolved! Looks like this issues here has re-emerged (although I don't know if it's to do with signing or encryption - seems to affect emails randomly. Both attachments and inline images in footers for me get wiped. Help please Microsoft, you've broken something! https://support.microsoft.com/en-us/topic/outlook-fails-to-send-attachments-and-inline-images-when-sending-a-signed-or-encrypted-email-using-the-new-outlook-for-mac-5719ab3c-70cd-4e19-8025-e51b7e055efa#articleFooterSupportBridge=communityBridge

Hi just chipping in here - Lots of our users (we have 250-300 active users) are (still) having this issue, all working on recent versions of 'new' Outlook for Mac. Not everybody is having the issue and i'm completely failing to recreate the same issue on my own Mac.While still 'randomly' affecting users, we do see this happening more and more often. For now we have suggested to switch back to 'old outlook' for most users but this is is definitely not a viable solution to us. MS is slow to respond on our support tickets as well.

ActionPlus I'm getting the same thing. Seems to be every time I send an attachment, regardless of whether it's a new mail I'm composing, a reply to a thread, or a mail I'm forwarding. What's interesting is, when the recipient complains and I add the same attachments to my apology, they are always sent second time around.I have a feeling this is related to OneDrive. I've had a few occasions recently where I've clicked to open a file that's synced with my local hdd and a message has appeared saying the file couldn't be found or a helper couldn't be found... something like that. Again, when I click on it a 2nd time, it opens fine.

We are having the same problem on two of our Macs. It is a bit random.

Dont think its OneDrive, we use Dropbox.

Outlook for Mac drops attachments | Microsoft Community Hub

33 Replies

Ryan099
Copper Contributor
Jul 07, 2023
Same issue here impacting all MacOS machines ActionPlus Currently having to use webmail.
MomentaOne
Copper Contributor
Jul 07, 2023
We are having the same problem on two of our Macs. It is a bit random.
Steve Holland
Copper Contributor
Jul 07, 2023
ActionPlus I'm getting the same thing. Seems to be every time I send an attachment, regardless of whether it's a new mail I'm composing, a reply to a thread, or a mail I'm forwarding. What's interesting is, when the recipient complains and I add the same attachments to my apology, they are always sent second time around.

I have a feeling this is related to OneDrive. I've had a few occasions recently where I've clicked to open a file that's synced with my local hdd and a message has appeared saying the file couldn't be found or a helper couldn't be found... something like that. Again, when I click on it a 2nd time, it opens fine.
- Steve Holland
  Copper Contributor
  Jul 13, 2023
  Update: Spoken to MS Outlook support and they've confirmed this is a bug which has been given a high priority to fix. It seems like a VERY SERIOUS bug to me, rendering one of their premier business tools effectively unusable. Let's see how long it takes them...
  - ActionPlus
    Copper Contributor
    Jul 13, 2023
    That's different to what they told me and I quote "365 for Mac is fully operational, this must be a glitch with your OS, we suggest you consult a MAC specialist !
- ActionPlus
  Copper Contributor
  Jul 07, 2023
  Dont think its OneDrive, we use Dropbox.
Dom_Conte
Copper Contributor
Jul 06, 2023
ActionPlus I'm also suffering from this and have had to move our entire team to webmail until this is resolved!

Looks like this issues here has re-emerged (although I don't know if it's to do with signing or encryption - seems to affect emails randomly.

Both attachments and inline images in footers for me get wiped.

Help please Microsoft, you've broken something!

https://support.microsoft.com/en-us/topic/outlook-fails-to-send-attachments-and-inline-images-when-sending-a-signed-or-encrypted-email-using-the-new-outlook-for-mac-5719ab3c-70cd-4e19-8025-e51b7e055efa#articleFooterSupportBridge=communityBridge

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Outlook for Mac drops attachments

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