Hello, DavidKelln,Welcome to Microsoft Community.
Thanks for your feedback, According to my understanding, after you created the restore point, you used an old restore point to go back to a previous state.
This should be due to the design of the feature; system restore points can only restore the system forward, and after restoration, restore points with a later time will be deleted.
Manually created restore points should not be automatically deleted as long as they meet the rules mentioned above. If you find that restore points have been deleted,you can also submit your questions through the FeedbackHub (if convenient, please provide as much detail as possible, including pictures, videos, etc.).
Send feedback to Microsoft with the Feedback Hub app
Please share the feedback link after submitting, I will submit your feedback to the relevant team for investigation through internal channels.
Wishing your problem an early resolution
If my understanding is wrong, please point it out, so that I can assist you better.
Lugoo Bei | Microsoft Community Support Specialist