This browser is no longer supported.
Upgrade to Microsoft Edge to take advantage of the latest features, security updates, and technical support.
![](data:image/svg+xml, %3Csvg xmlns='http://www.w3.org/2000/svg' height='64' class='font-weight-bold' style='font: 600 30.11764705882353px "SegoeUI", Arial' width='64'%3E%3Ccircle fill='hsl(128, 8%, 22%)' cx='32' cy='32' r='32' /%3E%3Ctext x='50%25' y='55%25' dominant-baseline='middle' text-anchor='middle' fill='%23FFF' %3EA%3C/text%3E%3C/svg%3E)
Hi everyone - has anyone had issues with sending emails using Outlook 365 for Macs? Especially a red error box that appears at the bottom (attached) and says "Message failed to send Open" The email is then stuck in drafts with the option to continue editing but it is simply frozen in drafts and the only way is to delete and try again. Alternatively, you can go to the webmail version of outlook, find the drafts folder and send from there. This has been happening on/off for several weeks now, no pattern, just happens occasionally.
This version of Outlook 365 is absolutely **** with so many issues
Using older versions of Outlook for Mac for personal email and calendar
Locked Question. This question was migrated from the Microsoft Support Community. You can vote on whether it's helpful, but you can't add comments or replies or follow the question.
Multiple people in my organisation are having the same issue.
I suggest everyone who is having this same issue open a support ticket, Microsoft does not appear to be listening to this thread.
That's when I found this thread. When support told me to raise it here and wouldn't raise an escalated but ticket or similar. :-/
Multiple people in my organisation are having the same issue.
I suggest everyone who is having this same issue open a support ticket, Microsoft does not appear to be listening to this thread.
This seems to be happening more and more for me, I'm on Outlook 16.88, but I have found a workaround that so far has worked every time. When this error comes up, I quit Outlook, re-launch, then click in the Inbox the email thread, and then on the Draft message in the thread I click 'Resume Editing' button on the right, then Send.
This is back. After a long time...this error is back.
I'm still having this issue, and I'm updated to the latest versions of Mac and Outlook.
I have to delete attachments in-line from signatures from other people's emails in a thread to work. Very frustrating.