Using Classic Outlook on Windows for personal email, calendar, and contact management
Hi youngbaseddave,
Thanks for choosing Microsoft Community.
Based on your description, I know your requirement. To better help you, I did a test for you. Please be kindly to make sure there some words in your message. If there are no words in message, the Toolbar will be grayed out. As you can see as the bellowing two pictures.
If you try to type some words in message and still meet the same issue, please be kindly to Repair an Office application and then check if it can make any difference.
Meanwhile, based on the screenshot you provided, it seems the outlook you use is not the latest, please update outlook to the latest version and check the result.
If there is any update, please feel free to let me know. I will continue to help you based on the information you provide. Your understanding is highly appreciated.
Thanks for your precious time. Have a nice day.
Best Regards,
Katherine