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.
I also have this same issue. About every 1/10 emails does not send and appears with the "Message failed to send" red error box.
Hopefully Microsoft fix this soon because it is very frustrating.
I've got a new issue in the past few days. When I reply to a message it show a small notification saying "creating draft" then the new message immediately is moved to drafts rather then open a new compose window. Happens about 50% of the time. The signatures and images are still being stripped. I tried removing all plugins (only had Hubspot) but didn't help
I still can't believe that 2+ weeks later this issue hasn't been resolved and seems to be getting worse.
What is anyone else on this ticket current status?
Another update - problems started again yesterday, for me its definitely when an email has embedded images and i'm replying or forwarding. After spending an hour or so in chat to Microsoft support, this time a dedicated team who look after Outlook for Macs, they finally admitted that they have received other calls relating to this and had been escalated to a senior tech to investigate and would probably be fixed in future updates!!!
Possible fix!!
Removed my auto signature from Replies and Forwarding, been working fine since then
Have been in contact with Microsoft support who appear to have no interest in solving this.
Get the usual rubbish - "What version of Mac, What version of Outlook" Blah blah blah!!
Would be cool but didn't work for me. I don't have a response signature at all. Hope it works out for you though!
Possible fix!!
Removed my auto signature from Replies and Forwarding, been working fine since then
Have been in contact with Microsoft support who appear to have no interest in solving this.
Get the usual rubbish - "What version of Mac, What version of Outlook" Blah blah blah!!