Hello Rick Kelley1,
Thank you for posting this case in Microsoft Community!
Based on your description: No spell check when writing a new message and you go to the dots in the right corner and scroll down and it shows Microsoft Editor but it is greyed out. Is there something I have to do to enable it? I would like to cooperate with you working on this case. To clarify this case, are you using New Outlook for Windows or Classic Outlook for Windows? Please kindly provide us your Outlook version with product details by going to New Outlook > Settings > General > About Outlook or Classic Outlook > File > Office Account and share that entire page screenshot with hide personal information. What version of Outlook do I have?
To fix this case, you may check following workaround:
- Firstly, you may check if Microsoft Editor options is working normally in Outlook Web or not. This will help to narrow down the issue if only exists on your Outlook client.
- If working fine in Outlook on the web, please go to Outlook>File>Options>Mail if you are using Classic Outlook and check Always check spelling before sending options if enabled or not. Then please also go to Spelling and Autocorrect... options to more settings if enabled. If not, please re-enable all of them as below captures.


- If you are using New Outlook, please follow the below rest steps further:
A. Please make sure if your New Outlook has been upgraded to the latest version.
B. Then Navigate to Settings > General > Privacy and Data > Privacy Settings. **** Please check if enabled Turn on optional connected experiences that analyze your content. If not, please enable it to check again.

C. Then you may perform the further steps as shared Microsoft article Troubleshooting Outlook for Windows issues.
D. Finally you may try to re-install the latest version of Office 365 application and check if working or not.
Download and install or reinstall Microsoft 365 or Office 2021 on a PC or Mac - Microsoft Support
If this case still persists in New Outlook, please also contact New Outlook for Windows Support Team via clicking Help>Contact Supportor Contact support and provide feedback within the new Outlook for Windows. The support team over there has higher permission than us, they can remotely help you and collect logs at your convenience. They can also involve more resources to investigate the issue from backend side. This would be the most efficient way in handling this case for you.
Hope the above workaround would be helpful. If you need further assistance, please feel free to let me know, I will keep assisting you.
Your understanding and patience will be appreciated.
Thank you!