Hi jacob.peters,
Please share the project file. Here in the forum as zipped, or I can provide an upload link. (Besides that, I open Google, Amazon, Dropbox, Apple, Adobe, and Wetransfer cloud services, nothing else, for security reasons.)
Images don’t tell me the whole story.
As usual, I want to give a solution, not a list of guesses. Images lead to guessing.
Speaking of guesses, try Timeline> View> Automatic Mode (alt/option + A, while the mouse indicator is inside the timeline editor)
All the best