HiKyle Hendrickson2,
Greetings!
Thank you for posting in Microsoft Community.
Based on the description you posted, it seems that you have an issue with Outlook wherein you are getting annoyed on the fact that the New Outlook auto capitalize feature doesn't work
By the way, it seems that you are not the only one that has been able to encounter this kind of problem.
Another user was also annoyed by this problem, on the other hand. Given that the New Outlook is still in preview, it is expected that some problems like this will arise.
That is why right now, it would be best if you submit a feedback about this issue. In order for the developers of the program to get notified and may apply a fix on this concern in the next upcoming updates.
You can directly provide a feedback to our developers of the New Outlook app by following the steps provided down below:
Help us improve the product by giving us feedback. To provide feedback, go to Help> Feedback.

Feedback will not be available if you disable the Optional connected experience. To enable Feedback, go to Settings > View all Outlook settings > General > Privacy and data > Privacy settingsand turn on the Optional connected experience.

Referenced link: Contact support and provide feedback within the new Outlook for Windows - Microsoft Support
Let me know if this helps,
Sincerely
Khou Sun
Microsoft Community Moderator