Outlook 365 for Mac - not sending attachments

I've now received a reply from Microsoft Support finally:

I would like to inform you that we have identified this behavior as a BUG and report is already filed with the product engineering team and the issue is under investigation. I understand the severity of the issue and the requirement for the resolution. Since this needs to be tested and the fix needs to be rolled out, we would not be able to provide an ETA on the fix. Once the fix is rolled out to any BUG filed with the product engineering team, then it'll be released through updates for Outlook. Hence, keep your Outlook updated. You may also refer to the Microsoft blog, where all the updates to the latest features and fixes are announced. Here is the link: https://docs.microsoft.com/en-us/officeupdates/release-notes-office-for-mac andhttps://support.office.com/en-us/article/Fixes-or-workarounds-for-recent-issues-in-Outlook-for-Mac-54afa5e3-db38-422a-9d94-3b55330ded8e/ As a work around you can revert back to legacy Outlook and continue using it until this BUG is resolved in new Outlook.Please follow the steps mentioned below to revert back to classic Outlook.

-Go to menu bar, click on Help. Select 'Revert back to Legacy Outlook' to switch to legacy Outlook.Thank you.

For the last 2+ months this issue has been driving me crazy and it's definitely unacceptable that Microsoft has yet to provide a fix for such an important issue.

Over the timeframe I have been encountering this issue, I've been stalking this message board and appreciate everyone's input and workarounds. Like many others, I have been composing my emails with attachments in the app, saving in drafts, and then eventually sending from the web version. I've tried installing both beta and regular updates, but nothing ever seems to be consistent.

With that being said, one of the more recent previous posts mentioned the possibility that Add-Ins could be causing the issue -- Particularly the HubSpot integration. Over the past few days, I have removed the HubSpot Add-In from my Outlook desktop app and this has worked like a charm. Since removing this and restarting the app, I have not had any problems successfully sending emails with attachments from the desktop app.

As a result, for those of you that have the HubSpot Add-In installed on your desktop app, I would recommend giving this a try to see if it works for you!

...knowing that we have all been through with this issue, it also wouldn't surprise me if I suddenly start having problems again :)

For Mac users: Switching to legacy Outlook solves the problem, or switching to Beta (I am a Mac user) can help. You can switch to Beta by using the steps here - Help menu > Check for updates > Advanced > Change the channel option to Beta > Check and get the available updates. However, you must ensure you have installed Office from Microsoft, not App Store. If you are not sure just uninstall and install again from your portal. You can download Office from your portal here. - https://portal.office.com/account/?ref=MeControl

I'm using Microsoft Outlook for Mac version 16.74.1 (23061800) on a 2021 14-inch M1 Pro MacBook Pro running Ventura 13.4.

I was getting the same issue of attachments looking like they were attached but not being received. I tried multiple updates of Outlook (standard channel, beta channel etc.), uninstalled / reinstalled, turned off antivirus, turned off VPN etc. and no difference. However I noticed that the issue started randomly rather than after an Outlook update - this was the clue that told me the issue was with Outlook itself and this morning I (fingers crossed) have resolved it.

From what I could gather it was a permission issue with macOS. I've had a number of applications (Microsoft and others) all have permissions issues since apple update macOS, so I checked the following in System Settings | Privacy & Security | Full Disk Access and made sure that all Microsoft (and other apps with issues) were included. Outlook wasn't there by default so I added it. I then checked that it had saved by checking the apps in Files and Folders were showing Full Disk Access.

I rebooted Outlook but it still had the same issue so I check permissions to 2 root folders where I know Outlook stores temporary data:

• My user folder (HD > Users > steve)
• My OneDrive folder

On both of these folders I went to 'Get Info' and checked the 'Sharing & Permissions'. I changed it so that 'everyone' and 'Steve (me)' had 'Read & Write' permissions. Closed Outlook and reopened and my test email with attachment was sent and received with the attachment.

Bit of an extreme fix (providing read & write permissions to all isn't great - but I have lots of security enabled to prevent unwanted access so not too bad), but it seems the issue is a permissions issue outside of Outlook. Or at least it was for me.

Hope the above helps someone else!

Same problem by a month now. I also tried to delete the account, unistall the Outlook app and reboot the entire system.

We cannot work like this so I do need to fix it.

Please update.

Tnx