Hi Roland,
Welcome to Microsoft Q&A Forum!
Have a good day and I hope you're doing well!
I completely understand how frustrating this UI issue must be for you. It is indeed very annoying to have your daily workflow disrupted by having to send separate emails just to add context to a meeting response.
Based on my testing in a virtual environment with Outlook version 16.106 (26020821) on macOS, everything appears to be working correctly on my end, and the action buttons remain visible when the "Email organiser" toggle is On.
Since I cannot reproduce this on my side, this might be an isolated glitch on your specific instance. Could you please try the following troubleshooting steps?
1. Check for Updates: First, please double-check to ensure that your Outlook client is updated to the absolute latest version available.
2. Clear the Cache: Sometimes, cached data can cause UI display errors. Please try clearing the cache to remove any potentially corrupted data: Clear the cache in Outlook for Mac
3. Re-add your Account: If the issue persists, try removing your email account and adding it back. This refreshes the configuration and often fixes strange UI behaviors.
While troubleshooting, if you need an immediate solution to avoid the "double-email" hassle, I suggest temporarily switching to Legacy Outlook.
In the Legacy interface, the Accept/Tentative/Decline buttons feature a dropdown arrow (Respond with Comments) as shown in the image below. This will allow you to add your message directly within the response, keeping your workflow smooth in the short term.
I hope this helps, at least partially. Please give the steps above a try and let me know how things go. If you have any concerns, questions, or if I misunderstood anything, please feel free to reach out anytime.
Best regards.
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