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.
Has this been fixed yet?!?
It is a year later and I am still having issues with emails not being sent and finding them in Drafts days later.
Come on Microsoft - is it too much to expect that Outlook can reliably send emails !!!!!
We currently have two users with this issue, very recently, since 16.83.2 update.
Waiting for this to slowly happen on our very important client who all use macs....
Hoping it is patched before then but
Legacy version of Outlook works just fine - it's very clearly a problem with the "new" app rather than anything else.
It does also seem to be replies in particular, probably with embedded images in them, haven't got that far yet!
I suppose I will have to raise a support request for this and spend about a month trying to communicate with support...
Please. Fix. This
It's almost like nobody at Microsoft is communicating...
This is causing continuous issues with our client comms. This is a pretty significant issue for an email service...
Hi Eleni,
I'm scratching my head as to why this bug is still around.
It's quite simple. As soon as you reply to a mail with sort sentence structures, it won't send. For instance, "Yes it's approved"
Then when changing it to "Hi John, Yes, the social post has been approved" it will send.
It's very frustrating when you want to do quick replies.
I hope it get's resolved soon!