Hello MasonThomas14,
Thanks for using Apple Support Communities! It looks like you're having trouble with the raise to wake feature on your Apple watch, and we'd like to help out.
Have you restarted your Apple Watch since noticing this issue? If not, go ahead and do that, as a restart can resolve unexpected issues. How to restart your Apple Watch
If you're still having the same issue, this article has what to check for: Turn on and wake Apple Watch
Scroll down to the section titled "Wake the Apple Watch display", to verify that is set up correctly. That article also has information on the Always On feature.
Here's more info on Aways On: Use the Always On feature with your Apple Watch Series 5
If your arm wasn't lowered enough to register the arm raise, you can also tap the display, or other actions. That info is shown in the above article, in the section titled "How to interact with your watch".
Take care!