Outlook for Mac - Flagged outgoing emails

Just dropping here a workaround I am using, in case anyone with a similar issues finds this conversation. I created a script on Power Automate that automatically flags an email if it is sent from my own address and has my address in BCC. So, everytime I want to flag for followup an outgoing email, I BCC myself. Not very elegant, but... it works (while hoping that this is fixed with a future update).

Thanks for looking further into this. I am afraid I will have to give up then. Only 1% of the corporate users have mac, so won't be getting focus on the topic. I found some other online posts on the topic, so it's not fully isolated, so... will keep hoping someday someone will fix it!

Hi @MassimoUn,

Thank you very much for your response and patience.

Based on your provided information, it appears the issue persists across both your old and current Mac devices, which suggests the root cause may be related to a configuration within your organization environment rather than the Outlook client itself.

To further support you, I’ve conducted deeper research and extensive testing on my Outlook end, including a review of potential configurations in Exchange Online, since it handles mail flow and could theoretically influence how flags behave across platforms.

However, I was unable to identify any settings in Exchange or in Outlook that would cause flagged messages to appear automatically for recipients. The flagging feature is specific to the Outlook client and should not apply to recipient emails without manual input, something only possible in Classic Outlook for Windows.

Given these findings, I recommend that you or your IT administrator raise a support ticket with the Microsoft Support Team via the Microsoft Admin Center. They’ll be able to investigate this further with access to more detailed diagnostic tools and environment-specific insights.

Thank you very much for your time and understanding.

Hi,

I am on the new outlook for mac, and the recipients I tried with are all on the classic outlook for windows. All the accounts are business accounts, from the same company. The issue was already happening on a previous mac, and it happend again on this new one where all the software is updated to the last version and a fresh installation had just been performed.

I cannot use Outlook Web only, as I need to use the computer on the move.

Hi @MassimoUn,

Welcome to the Microsoft Q&A forum, and thank you for reaching out.

Please note that this is the It-It forum. We recommend posting your question in Italian so that more community members can help you. Alternatively, you can also consider posting in the US-EN forum if you prefer to use your native language. We sincerely appreciate your understanding.

Based on your description, it appears that when you flag an outgoing email in the new Outlook for Mac, the recipient using Outlook for Windows also sees the flagged email. Please feel free to correct me if I misunderstand your scenario.

Please note that, as a Microsoft Q&A moderator, my ability to test in macOS environments is limited. However, I will do my best to assist you using the available documentation and resources.

To help us investigate further, could you please confirm the following:

• Are you using a personal or business account (Microsoft 365 for work/school)?
• Does this issue occur when sending to internal, external, or both recipients?
• Have you tested this behavior with multiple recipients to see if the flag always appears on their end?
• Have you tried using Outlook Web App to flag an outgoing email, and does the same behavior occur?

Based on my test, when I try to replicate your issue by sending an email using the new Outlook on macOS to a recipient using the new Outlook on Windows and flagging the message before sending:

On my end: The flag is visible only to me (the sender).

On the recipient's end: The recipient doesn't see the message as flagged.

For potential fix, if the issue only occurs in the new Outlook for Mac, you can try the following general troubleshooting steps commonly recommended for Outlook:

Sign out and sign back in to your Outlook account to see if the issue persists.

Make sure Outlook is up to date by going to Help > Check for Updates and installing any available updates.

If the issue persists, consider reinstalling the latest version of Outlook to ensure a clean installation.

As a workaround, try using Outlook Web App to send a flagged email. If the issue doesn't occur, I recommend temporarily using OWA to mitigate the issue in the meantime.

Please note that while our initial response may not immediately resolve the issue, your input is extremely valuable in helping us better understand the situation. With more details, we will work together to identify the most effective solution for you.

I look forward to your response.

Note: Please follow the steps in our documentation to enable e-mail notifications if you want to receive the related email notification for this thread.