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.
Can confirm switching to the legacy view fixes it, but with so many users experiencing the same thing on Mac we really shouldn't have to. Crazy that it's gone unaddressed for this long.
I have exactly the same issue, for now I'm reverting back to the 'classic' Outlook version.
Work helpdesk for an MSP. One of our clients is starting to experience this issue as well. Random occurrences on different Macbooks throughout the user base... Extremely frustrating, especially when many users do not want to adjust their normal workflows.
I'm writing to support everyone else who has shared their concerns in this thread, as I have started to have the same issue since the 4th of March.
Really hoping that Microsoft's big team and vast resources can address this seemingly insignificant bug.
Is there any progress Microsoft?
Hi @Microsoft, any progress? I'm having this issue for a year now. I think it started happening when I switched on the Send later option, but disabling it does not fix the issue now. VERY FRUSTRATING, as you think those mails are sent but they never left your draft Box. They are not even in the outbox.
Please fix it!